Ibuprofen

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Identification

Summary

Ibuprofen is an NSAID and non-selective COX inhibitor used to treat mild-moderate pain, fever, and inflammation.

Brand Names

Addaprin, Advil, Advil Cold and Sinus, Advil Congestion Relief, Advil PM, Advil Sinus Congestion and Pain, Alivio, Caldolor, Cedaprin, Children's Ibuprofen, Combogesic, Diphen, Duexis, Ibu, Ibutab, Junior Strength Motrin, Motrin, Motrin PM, Neoprofen, Nuprin, Pedea, Proprinal, Reprexain, Sudafed PE Head Congestion Plus Pain, Vicoprofen, Wal-profen Congestion Relief and Pain

Generic Name

Ibuprofen

DrugBank Accession Number

DB01050

Background

Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and it is considered the first of the propionics.⁷ The formula of ibuprofen is 2-(4-isobutylphenyl) propionic acid and its initial development was in 1960 while researching for a safer alternative for aspirin.⁸ Ibuprofen was finally patented in 1961 and this drug was first launched against rheumatoid arthritis in the UK in 1969 and USA in 1974. It was the first available over-the-counter NSAID.⁹

On the available products, ibuprofen is administered as a racemic mixture. Once administered, the R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo by the activity of the alpha-methylacyl-CoA racemase. In particular, it is generally proposed that the S-enantiomer is capable of eliciting stronger pharmacological activity than the R-enantiomer.²⁴

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 206.2808
Monoisotopic: 206.13067982
Chemical Formula: C₁₃H₁₈O₂

Synonyms

(±)-2-(p-isobutylphenyl)propionic acid
(±)-ibuprofen
(±)-p-isobutylhydratropic acid
(±)-α-methyl-4-(2-methylpropyl)benzeneacetic acid
(4-isobutylphenyl)-α-methylacetic acid
(RS)-ibuprofen
2-(4-isobutylphenyl)propanoic acid
4-isobutylhydratropic acid
Ibuprofen
Ibuprofene
Ibuprofeno
Ibuprofenum
Ibuprophen
α-(4-isobutylphenyl)propionic acid
α-(p-isobutylphenyl)propionic acid

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Pharmacology

Indication

Ibuprofen is the most commonly used and prescribed NSAID. It is a very common over-the-counter medication widely used as an analgesic, anti-inflammatory and antipyretic.¹¹

The use of ibuprofen and its enantiomer Dexibuprofen in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.¹²

Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labour.¹⁰

As ibuprofen is a widely used medication, the main therapeutic indications are:

Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open.¹³
Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders.¹⁴
Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs.¹⁵
Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension.¹
Dental pain - ibuprofen is used to manage acute and chronic orofacial pain.¹⁶
Pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches.¹⁰ It is also used to manage mild to moderate pain and moderate to severe pain as an adjunct to opioid analgesics.²⁸
Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.¹⁰

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Used in combination to manage	Acute pain	Combination Product in combination with: Hydrocodone (DB00956)	••••••••••••
Used in combination to manage	Acute pain	Combination Product in combination with: Oxycodone (DB00497)	••••••••••••
Management of	Ankylosing spondylitis		••• •••••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Phenylephrine (DB00388), Desloratadine (DB00967)	••• •••	•••••••• ••••••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Cetirizine (DB00341), Phenylephrine (DB00388)	••• •••	•••••••• ••••••• •••••••• •••••• ••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials.²³

The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region.²³

The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen.²³

The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms.¹⁰

Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility.¹⁷ As well, it has been reported to reduce significantly the fever and the pain caused by migraines.^18,19 This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system.²³

In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time.²⁰ On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition.²¹ The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.²²

Mechanism of action

The exact mechanism of action of ibuprofen is unknown. However, ibuprofen is considered an NSAID and thus it is a non-selective inhibitor of cyclooxygenase, which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway.²⁷

Ibuprofen is a non-selective COX inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration.²⁵

Target	Actions	Organism
AProstaglandin G/H synthase 2	inhibitor	Humans
AC-X-C chemokine receptor type 2	inhibitor	Humans
AInterleukin-8	inhibitor	Humans
AC-X-C chemokine receptor type 1	inhibitor	Humans
AProstaglandin G/H synthase 1	inhibitor	Humans
UApoptosis regulator Bcl-2	modulator	Humans
UThrombomodulin	inducer	Humans
UFatty acid-binding protein, intestinal	binder	Humans
UPeroxisome proliferator-activated receptor gamma	activator	Humans
UCystic fibrosis transmembrane conductance regulator	inhibitor	Humans
UPeroxisome proliferator-activated receptor alpha	activator	Humans
UPlatelet glycoprotein Ib alpha chain	inducer	Humans
UProtein S100-A7	inducer	Humans

Absorption

It is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption.¹⁰

When orally administered, the absorption of ibuprofen in adults is very rapidly done in the upper GI tract.²³ The average Cmax, Tmax and AUC ranges around 20 mcg/ml, 2 h and 70 mcg.h/ml. These parameters can vary depending on the enantiomer form, route, and dose of administration.²³

Volume of distribution

The apparent volume of distribution of ibuprofen is of 0.1 L/kg.²⁵

Protein binding

Ibuprofen dosage is more than 99% bound to plasma proteins and site II of purified albumin, binding appears to be saturable and becomes non-linear at concentrations exceeding 20 mcg/ml.¹⁰

Metabolism

Ibuprofen is rapidly metabolized and biotransformed in the liver to the formation of major metabolites which are the hydroxylated and carboxylated derivatives.¹⁰ As soon as it is absorbed, the R-enantiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer in vivo by the activity of alpha-methylacyl-CoA racemase.²⁴

Ibuprofen metabolism can be divided in phase I which is represented by the hydroxylation of the isobutyl chains for the formation of 2 or 3-hydroxy derivatives followed by oxidation to 2-carboxy-ibuprofen and p-carboxy-2-propionate. These oxidative reactions are performed by the activity of the cytochrome P450 isoforms CYP 2C9, CYP 2C19 and CYP 2C8. Therefore, these enzymes participate in the oxidation of the alkyl side chain to hydroxyl and carboxyl derivatives. From this enzymes, the major catalyst in the formation of oxidative metabolites is the isoform CYP 2C9.²³

The metabolic phase I is followed by a phase II in which the oxidative metabolites may be conjugated to glucuronide prior to excretion. This activity forms phenolic and acyl glucuronides.²³

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Ibuprofen

Route of elimination

Ibuprofen is rapidly metabolized and eliminated in the urine thus, this via accounts for more than 90% of the administered dose. It is completely eliminated in 24 hours after the last dose and almost all the administered dose goes through metabolism, representing about 99% of the eliminated dose.¹⁰ The biliary excretion of unchanged drug and active phase II metabolites represents 1% of the administered dose.²³

In summary, ibuprofen is excreted as metabolites or their conjugates. The elimination of ibuprofen is not impaired by old age or the presence of renal impairment.¹⁰

Half-life

The serum half-life of ibuprofen is 1.2-2 hours.¹⁰ In patients with a compromised liver function, the half-life can be prolonged to 3.1-3.4 hours.²³

Clearance

The clearance rate ranges between 3-13 L/h depending on the route of administration, enantiomer type and dosage.²³

Adverse Effects

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Toxicity

The symptoms of overdose are presented in individuals that consumed more than 99 mg/kg. Most common symptoms of overdose are abdominal pain, nausea, vomiting, lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other symptoms of overdose include headache, loss of consciousness, tinnitus, CNS depression, convulsions and seizures. May rarely cause metabolic acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea, respiratory depression, coma, acute renal failure, and apnea (primarily in very young pediatric patients).²⁶

The reported LD50 of ibuprofen is of 636 mg/kg in rat, 740 mg/kg in mouse and 495 mg/kg in guinea pig.^MSDS

Pathways

Pathway	Category
Ibuprofen Action Pathway	Drug action
Ibuprofen Metabolism Pathway	Drug metabolism

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Ibuprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Ibuprofen can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Ibuprofen can be increased when combined with Abatacept.
Abciximab	The risk or severity of bleeding can be increased when Ibuprofen is combined with Abciximab.
Abiraterone	The metabolism of Ibuprofen can be decreased when combined with Abiraterone.

Food Interactions

Avoid alcohol.
Take with food. Food reduces irritation.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ibuprofen aluminum	D0YGZ1VO1B	61054-06-6	QAZIXAUMDFPQRW-UHFFFAOYSA-K
Ibuprofen arginine	XV17W49C9U	57469-82-6	GCCOJNYCFNSJII-VWMHFEHESA-N
Ibuprofen lysine	N01ORX9D6S	57469-77-9	IHHXIUAEPKVVII-ZSCHJXSPSA-N
Ibuprofen potassium	48304089JJ	79261-49-7	XJELUCTZEAQYGF-UHFFFAOYSA-M
Ibuprofen sodium	RM1CE97Z4N	527688-20-6	VTGPMVCGAVZLQI-UHFFFAOYSA-M

Product Images

International/Other Brands

Act-3 (Healthcare Logistics) / Actiprofen (Sterling Health) / Adex (Dexxon) / Aktren (Bayer) / Alges-X (Axapharm) / Algoflex (Chinoin) / Algofren (Intermed) / Alivium (Bristol-Myers Squibb) / Artofen (Teva) / Betagesic (Adcock Ingram Pharmaceuticals) / Betaprofen (Be-Tabs Pharmaceuticals) / Bonifen (Krka) / Brufen (Abbott) / Brupro (Sandoz) / Buburone (Towa Yakuhin) / Buprovil (Multilab Industry and Trade of Pharmaceuticals) / Burana (Orion) / Butylenin (Sanken) / Calprofen (McNeil) / Cap-Profen (PERRIGO) / Capsibu (Sandoz) / Children's Elixsure (Pfizer) / Children's Ibuprofen (Pfizer) / Dalsy (Abbott) / Dismenol (Merz) / Diverin (ACI Ltd) / Dolgirid (LGC) / Dolgit (Dolorgiet) / Doloraz (Jordanian Pharmaceutical Manufacturing Co.) / Dolormin (Johnson & Johnson GmbH) / Ebufac (DDSA Pharmaceuticals) / EmuProfen (Progressive Emu, Inc) / Epobron (Ono) / Fenbid (Smith Kline and Beecham) / Fenpaed (Rite Aid Corporation) / Fenpain (Sandoz) / Ibalgin (Zentiva) / IBU-Ratiopharm (Ratiopharm GmbH) / Ibuflam (Natco Pharma Ltd) / Ibugel (Dermal Laboratories Ltd) / Ibugesic (Cipra Ltd) / IbuHEXAL (Hexal AG) / Ibuleve (Diomed Development Ltd) / Ibum (PPF Hasco-Lek SA) / Ibumax (standford Biotech Pvt Ltd) / Ibumetin (Nycomed Denmark Aps) / Ibupain (Sandoz) / Ibuprocin (Nisshin) / Ibuprom (USP Zdrowie) / Ibuprox (Norway) / Ibustar (Berlin-Chemie Menarini Croatia) / Ibutren (Sandoz) / Ibux (Weifa AS) / Ibuxin (Pliva Hrvatska) / Junior Strength Motrin (J&J Consumer Inc) / Kratalgin (Austria) / Lamidon (Kowa) / Lebrufen / Liptan (Kowa) / Lotem (Adcock Ingram) / Medicol (United Lab) / Medipren (Johnson & Johnson) / Mynosedin (Toho Yakuhin) / Mypaid (Ai Pharm) / Myprodol (Adcock Ingram) / Narfen (Alter) / Naron Ace (Primary Care Tokyo) / Neobrufen (Crookes) / Nobfen (Toho) / Nobgen (Toho) / Norvectan / Nuprin (Upjohn Company) / Nureflex (Boots Healthcare, Courbevoie) / Nurofen (Crookes) / Orbifen (Boehringer Ingelheim International GmbH) / Panafen (GlaxoSmithKline Consumer Healthcare Australia Pty Ltd) / Pediaprofen (Whitehall Laboratories) / Rapidol (Actavis) / Rimafen / Roidenin (Showa) / Rufen (Boots) / Salvarina (Salvat, Barcelona) / Seclodin (Whitehall Labs, Maidenhead) / Speedpain NANO (Goodsense) / Spidifen (Zambon) / Suspren / Tabalon (Sanofi India Ltd) / Trendar (Whitehall-Robins) / Urem (Kade, MErlin)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Caldolor	Injection	800 mg/200mL	Intravenous	Cumberland Pharmaceuticals Inc.	2020-01-01	Not applicable
Caldolor	Injection	800 mg/8mL	Intravenous	Cumberland Pharmaceuticals Inc.	2009-06-11	Not applicable
Caldolor	Solution	100 mg / mL	Intravenous	Cumberland Pharmaceuticals Inc	2012-06-15	Not applicable
Caldolor	Injection	100 mg/1mL	Intravenous	Cumberland Pharmaceuticals Inc.	2009-08-27	2009-06-24
Ibupak	Kit	600 mg/1	Oral	PureTek Corporation	2020-05-22	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Alivio	Tablet	600 mg/600mg	Oral	Alivio Medical Products, Llc	2015-07-01	Not applicable
Alivio	Tablet	800 mg/800mg	Oral	Alivio Medical Products, Llc	2015-07-01	Not applicable
Alivio	Tablet	400 mg/400mg	Oral	Alivio Medical Products, Llc	2015-07-01	Not applicable
Alti-ibuprofen Tab 600mg	Tablet	600 mg	Oral	Altimed Pharma Inc.	1984-12-31	1999-09-17
Apo-ibuprofen Tab 600mg	Tablet	600 mg	Oral	Apotex Corporation	1984-12-31	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
24/7 Life IBUPROFEN	Tablet, film coated	200 mg/1	Oral	Lil' Drug Store Products, Inc.	2020-12-16	Not applicable
365 Everday Value Ibuprofen	Tablet, film coated	200 mg/1	Oral	Whole Foods Market, Inc.	2020-08-24	Not applicable
365 Everyday Value Ibuprofen	Tablet, film coated	200 mg/1	Oral	Whole Foods Market, Inc.	2018-08-29	Not applicable
7 Select Childrens Ibuprofen	Suspension	100 mg/5mL	Oral	7-Eleven	2014-08-05	2021-04-30
7 Select Ibuprofen	Capsule, liquid filled	200 mg/1	Oral	7-Eleven	2018-02-02	2021-03-31

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
10 Person ANSI	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-24	Not applicable
25 Person ANSI	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Genuine First Aid	2010-04-25	Not applicable
4389 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (2 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4390 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4392 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
4389 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (2 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4390 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4392 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4395 First Aid Kit	Ibuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Benzalkonium chloride (1.3 mg/1mL) + Benzalkonium chloride (0.13 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g)	Cream; Kit; Liquid; Ointment; Swab; Tablet	Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
Cimetidine 5% / Ibuprofen 2% / Salicylic Acid 17%	Ibuprofen (2 g/100g) + Cimetidine (5 g/100g) + Salicylic acid (17 g/100g)	Gel	Topical	Sincerus Florida, LLC	2019-05-17	Not applicable

Chemical Identifiers

UNII: WK2XYI10QM
CAS number: 15687-27-1
InChI Key: HEFNNWSXXWATRW-UHFFFAOYSA-N
InChI: InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
IUPAC Name: 2-[4-(2-methylpropyl)phenyl]propanoic acid
SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

References

General References

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Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, Ascherio A: Nonsteroidal antiinflammatory drug use and the risk for Parkinson's disease. Ann Neurol. 2005 Dec;58(6):963-7. [Article]
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Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [Article]
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Rainsford KD: Discovery, mechanisms of action and safety of ibuprofen. Int J Clin Pract Suppl. 2003 Apr;(135):3-8. [Article]
Halford GM, Lordkipanidze M, Watson SP: 50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams. Platelets. 2012;23(6):415-22. doi: 10.3109/09537104.2011.632032. Epub 2011 Nov 18. [Article]
Bushra R, Aslam N: An overview of clinical pharmacology of Ibuprofen. Oman Med J. 2010 Jul;25(3):155-1661. doi: 10.5001/omj.2010.49. [Article]
Adams SS, McCullough KF, Nicholson JS: The pharmacological properties of ibuprofen, an anti-inflammatory, analgesic and antipyretic agent. Arch Int Pharmacodyn Ther. 1969 Mar;178(1):115-29. [Article]
Potthast H, Dressman JB, Junginger HE, Midha KK, Oeser H, Shah VP, Vogelpoel H, Barends DM: Biowaiver monographs for immediate release solid oral dosage forms: ibuprofen. J Pharm Sci. 2005 Oct;94(10):2121-31. doi: 10.1002/jps.20444. [Article]
Sharma PK, Garg SK, Narang A: Pharmacokinetics of oral ibuprofen in premature infants. J Clin Pharmacol. 2003 Sep;43(9):968-73. [Article]
Tan SC, Patel BK, Jackson SH, Swift CG, Hutt AJ: Ibuprofen stereochemistry: double-the-trouble? Enantiomer. 1999;4(3-4):195-203. [Article]
Konstan MW, Krenicky JE, Finney MR, Kirchner HL, Hilliard KA, Hilliard JB, Davis PB, Hoppel CL: Effect of ibuprofen on neutrophil migration in vivo in cystic fibrosis and healthy subjects. J Pharmacol Exp Ther. 2003 Sep;306(3):1086-91. doi: 10.1124/jpet.103.052449. Epub 2003 Jun 13. [Article]
Moore PA, Hersh EV: Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. J Am Dent Assoc. 2001 Apr;132(4):451-6. [Article]
Dawood MY: Primary dysmenorrhea: advances in pathogenesis and management. Obstet Gynecol. 2006 Aug;108(2):428-41. doi: 10.1097/01.AOG.0000230214.26638.0c. [Article]
Krishna S, Pukrittayakamee S, Supanaranond W, ter Kuile F, Ruprah M, Sura T, White NJ: Fever in uncomplicated Plasmodium falciparum malaria: randomized double-'blind' comparison of ibuprofen and paracetamol treatment. Trans R Soc Trop Med Hyg. 1995 Sep-Oct;89(5):507-9. [Article]
Evers S, Rahmann A, Kraemer C, Kurlemann G, Debus O, Husstedt IW, Frese A: Treatment of childhood migraine attacks with oral zolmitriptan and ibuprofen. Neurology. 2006 Aug 8;67(3):497-9. doi: 10.1212/01.wnl.0000231138.18629.d5. Epub 2006 Jun 14. [Article]
Casper D, Yaparpalvi U, Rempel N, Werner P: Ibuprofen protects dopaminergic neurons against glutamate toxicity in vitro. Neurosci Lett. 2000 Aug 11;289(3):201-4. [Article]
Ton TG, Heckbert SR, Longstreth WT Jr, Rossing MA, Kukull WA, Franklin GM, Swanson PD, Smith-Weller T, Checkoway H: Nonsteroidal anti-inflammatory drugs and risk of Parkinson's disease. Mov Disord. 2006 Jul;21(7):964-9. doi: 10.1002/mds.20856. [Article]
Harris RE, Kasbari S, Farrar WB: Prospective study of nonsteroidal anti-inflammatory drugs and breast cancer. Oncol Rep. 1999 Jan-Feb;6(1):71-3. [Article]
Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]
Tracy TS, Hall SD: Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A. Drug Metab Dispos. 1992 Mar-Apr;20(2):322-7. [Article]
Rao P, Knaus EE: Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci. 2008 Sep 20;11(2):81s-110s. [Article]
Hall AH, Smolinske SC, Conrad FL, Wruk KM, Kulig KW, Dwelle TL, Rumack BH: Ibuprofen overdose: 126 cases. Ann Emerg Med. 1986 Nov;15(11):1308-13. [Article]
Current issues in pharmacy and medical sciences [Link]
FDA Approved Drug Products: Caldolor (ibuprofen) solution for intravenous injection [Link]

External Links

Human Metabolome Database: HMDB0001925
KEGG Drug: D00126
KEGG Compound: C01588
PubChem Compound: 3672
PubChem Substance: 46507255
ChemSpider: 3544
BindingDB: 50009859
RxNav: 5640
ChEBI: 5855
ChEMBL: CHEMBL521
Therapeutic Targets Database: DAP000780
PharmGKB: PA449957
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Ibuprofen

FDA label

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MSDS

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Clinical Trials

Clinical Trials Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Active Not Recruiting	Not Available	Myocardial Dysfunction / Newborn Morbidity / Obesity, Maternal	1	somestatus	stop reason	just information to hide
Not Available	Active Not Recruiting	Prevention	Opioid Misuse / Opioids Use / Pain / Postoperative pain	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Adverse Events / Overdose	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Aging / Physical Fitness	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Concussion, Brain / Headache	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Abbott Laboratories Ltd.
Actavis Group
Advanced Pharmaceutical Services Inc.
Aidarex Pharmacuticals LLC
Altura Pharmaceuticals Inc.
Amerisource Health Services Corp.
Amneal Pharmaceuticals
Apotheca Inc.
Apothecary Shop Wholesale
A-S Medication Solutions LLC
Ascend Laboratories LLC
Atlantic Biologicals Corporation
BASF Corp.
Bayer Healthcare
Ben Venue Laboratories Inc.
Blenheim Pharmacal
Breckenridge Pharmaceuticals
Bryant Ranch Prepack
Bv Pharbita
Cardinal Health
Caremark LLC
Central Texas Community Health Centers
Centrix Pharmaceuticals
Chain Drug
Corepharma LLC
Coupler Enterprises Inc.
Cumberland Pharmaceuticals
CVS Pharmacy
Darby Dental Supply Co. Inc.
Dept Health Central Pharmacy
DHHS Program Support Center Supply Service Center
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Doctor Reddys Laboratories Ltd.
Dorx LLC
Eckerd
Equaline Vitamins
Gm Pharmaceuticals Inc.
Golden State Medical Supply Inc.
Greenstone LLC
Group Health Cooperative
H and H Laboratories
H.J. Harkins Co. Inc.
Hawthorn Pharmaceuticals
Heartland Repack Services LLC
Hl Moore Drug Exchange
Imiren Pharmaceuticals Inc.
Innoviant Pharmacy Inc.
Ivax Pharmaceuticals
Kaiser Foundation Hospital
Keltman Pharmaceuticals Inc.
Kowa Pharmaceuticals America Inc.
Lake Erie Medical and Surgical Supply
LeaderPharma
Legacy Pharmaceuticals Packaging LLC
Liberty Pharmaceuticals
Lundbeck Inc.
Major Pharmaceuticals
Mckesson Corp.
McNeil Laboratories
Medicine Shop
Medique Products
Medisca Inc.
Medvantx Inc.
Murfreesboro Pharmaceutical Nursing Supply
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
Particle Dynamics Co.
Patient First Corp.
PCA LLC
PD-Rx Pharmaceuticals Inc.
Perrigo Co.
Pharmaceutical Association
Pharmaceutical Utilization Management Program VA Inc.
Pharmacia Inc.
Pharmedix
Physicians Total Care Inc.
Poly Pharmaceuticals Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Prescript Pharmaceuticals
Prescription Dispensing Service Inc.
Publix Super Markets
Qualitest
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Resource Optimization and Innovation LLC
Rite Aid Corp.
Sandhills Packaging Inc.
Shanghai Ziyuan Pharmaceutical Co. Ltd.
Shasun Chemicals & Drugs Ltd.
Southwood Pharmaceuticals
St Mary's Medical Park Pharmacy
Stat Rx Usa
Sunmark
Talbert Medical Management Corp.
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Ultras Pharmaceuticals Inc.
Va Cmop Dallas
Vangard Labs Inc.
Veratex Corp.
Vintage Pharmaceuticals Inc.
Vistapharm Inc.
Walgreen Co.
Watson Pharmaceuticals
Wyeth Pharmaceuticals
Xactdose Inc.

Dosage Forms

Form	Route	Strength
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; swab; tablet	Oral; Topical
Kit	Ophthalmic; Oral; Topical
Tablet	Not applicable
Injection, powder, for solution	Intramuscular
Capsule	Oral	400.000 mg
Gel	Cutaneous	5.00 g
Capsule, liquid filled	Oral	600 mg
Tablet, sugar coated	Oral
Suspension	Oral	400 mg
Kit	Oral; Topical
Kit	Topical
Tablet, coated	Topical	200 mg/1
Tablet	Oral	600.000 mg
Tablet, extended release	Oral	600 mg
Capsule; kit	Oral
Tablet, coated	Oral	200 mg
Tablet, coated	Oral	256 mg/1
Tablet, coated	Oral	200 mg/1000mg
Suspension	Oral	2.000 g
Capsule	Oral
Capsule	Oral	200 mg
Capsule	Oral	200.000 mg
Capsule	Oral	600.000 mg
Capsule	Oral	200.000 mg
Suspension	Oral	20 MG/ML
Tablet	Oral	400 mg/400mg
Tablet	Oral	600 mg/600mg
Tablet	Oral	800 mg/800mg
Suspension	Oral	100 mg
Tablet	Oral	200 mg
Tablet	Oral	300 mg
Tablet	Oral	600 mg
Capsule	Oral	600.0000 mg
Tablet	Oral	1212.100 mg
Capsule	Oral	250 MG
Injection, powder, for solution	Intramuscular	400 MG/3ML
Injection, solution	Intramuscular	400 MG/3ML
Solution	Intramuscular	400 mg/3ml
Solution	Vaginal	10 MG/ML
Suppository	Rectal	250 MG
Tablet	Oral	500 MG
Tablet	Oral	20.000 mg
Gel	Topical	5 g
Solution	Intravenous	10 mg
Tablet	Oral	800.00 mg
Cream	Topical	10 G/100G
Cream	Topical	30 G
Pill		300 MG
Pill		400 MG
Tablet, coated		600 MG
Tablet, coated		800 MG
Tablet, film coated	Oral
Tablet, coated	Oral	400 mg
Tablet, delayed release	Oral	800 mg
Ointment	Topical
Powder, for solution	Oral
Suspension	Oral	200 mg/5mL
Suspension	Oral	200000 g
Powder	Oral	200 MG
Powder	Oral	400 MG
Injection	Intravenous
Injection	Intravenous	100 mg/1mL
Injection	Intravenous	800 mg/200mL
Injection	Intravenous	800 mg/8mL
Solution	Intravenous	100 mg / mL
Granule	Oral	2.2 g
Suspension	Oral	100 mg / 5 mL
Tablet, chewable	Oral	50 mg
Tablet	Oral	50 mg
Solution	Oral	100 mg/5mL
Suspension	Oral	200 mg/10mL
Suspension / drops	Oral	100 mg/5mL
Suspension	Oral	100 mg/10mL
Suspension	Oral
Tablet, delayed release	Oral
Gel	Topical
Kit; tablet	Oral
Tablet, film coated
Injection	Intravenous
Solution	Intravenous
Kit; tablet	Oral	800 mg/1
Powder	Not applicable	66 mg/100mg
Powder		85 mg/100mg
Syrup	Oral
Capsule, liquid filled	Oral	200 mg/1
Patch	Topical
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated	Oral; Topical
Gel	Topical	50 mg/g
Gel	Topical
Liquid	Oral	100 mg/100mL
Cream	Topical
Cream	Topical	5 %
Tablet, sugar coated	Oral	400 mg/1
Tablet, sugar coated	Oral	600 mg/1
Gel	Topical	400 mg/1
Capsule	Oral	50 mg/g
Suspension	Oral	200000000 mg
Solution / drops	Oral
Capsule, liquid filled	Oral	200 mg
Suspension	Oral	40 MG/ML
Capsule, coated	Oral	200 mg
Gel	Topical	10 %
Injection, solution	Intravenous	400 mg/100ml
Injection, solution, concentrate	Intravenous	20 mg/2ml
Capsule, liquid filled	Oral	200 mg/1201
Powder, for solution	Vaginal
Solution	Vaginal
Powder	Oral	0.2 g
Granule	Oral	200 mg
Granule	Oral	13.33 g
Suspension	Oral	40.000 mg
Solution	Topical
Pill
Tablet, orally disintegrating	Oral	200 MG
Suspension	Oral	4 g
Granule, effervescent	Oral	200 MG
Granule, effervescent	Oral	400 MG
Capsule	Oral	400.000000 mg
Capsule	Oral
Capsule	Oral	600 mg
Suspension	Oral	50 mg/1.25mL
Tablet, film coated	Oral
Suppository	Rectal
Tablet, film coated	Oral	293 MG
Tablet, film coated	Oral	500 MG
Syrup	Oral	20 MG/ML
Syrup	Oral	40 MG/ML
Tablet, film coated	Oral	800 MG
Powder; powder, for solution; powder, for suspension	Oral	200 MG
Powder; powder, for solution; powder, for suspension	Oral	400 MG
Tablet, film coated	Oral	684 MG
Syrup	Oral	100 mg
Tablet, extended release	Oral	800 MG
Suppository	Rectal	60 mg
Patch	Topical	136 MG
Solution	Oral	40 mg
Tablet, film coated	Oral	100 mg
Injection, solution		5 mg/ml
Capsule, coated	Oral	200 mg/1
Capsule, liquid filled	Oral	200 mg/2001
Kit; tablet, film coated	Oral
Suspension	Oral	100 mg/5mL
Tablet	Not applicable	200 mg/1
Tablet	Oral
Tablet	Oral	0.2 g/1g
Tablet	Oral	200 mg/1
Tablet	Oral	400 mg/1
Tablet	Oral	600 mg/1
Tablet	Oral	800 mg/1
Tablet, coated	Oral	200 mg/1
Tablet, coated	Oral	400 mg/1
Tablet, coated	Oral	600 mg/1
Tablet, coated	Oral	800 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	200 1/1
Tablet, film coated	Oral	200 mg/1 1
Tablet, film coated	Oral	256 mg/1
Tablet, film coated	Oral	400 mg/301
Tablet, film coated	Oral	400 mg/400mg
Tablet, film coated	Oral	400 mg/1
Tablet, film coated	Oral	600 mg/1
Tablet, film coated	Oral	600 mg/600mg
Tablet, film coated	Oral	800 mg/1
Tablet, film coated	Oral	800 mg/800mg
Tablet, sugar coated	Oral	200 mg/1
Capsule, extended release	Oral	400 MG
Suppository	Rectal	500 MG
Capsule	Oral	200 mg/1
Suppository	Rectal	600 mg
Tablet, sugar coated	Oral
Solution	Parenteral
Solution		4 mg/ml
Solution		6 mg/ml
Tablet, chewable	Oral
Tablet, chewable	Oral	100 mg/1
Solution	Parenteral	400 mg
Suspension	Oral
Capsule, liquid filled	Oral
Gel	Topical	50 mg
Granule	Oral	400 MG
Granule	Oral	600 MG
Syrup	Oral
Granule	Oral
Injection, solution
Granule, effervescent	Oral	600 MG
Injection, solution		400 MG
Injection, solution		600 MG
Injection, solution	Intravenous	5 mg/mL
Suspension	Oral	200 MG
Tablet, coated	Oral	4000 mg
Suspension	Oral	2 g
Tablet, coated	Oral	470.5882 mg
Tablet, delayed release	Oral	400 mg
Solution	Intravenous	4 mg/mL
Solution, concentrate	Intravenous	600 mg
Tablet, coated	Oral	800 mg
Tablet, delayed release	Oral	600 mg
Suspension	Oral	200 g
Suspension	Oral	2.0832 g
Tablet, delayed release	Oral	200 mg
Capsule, gelatin coated
Cream	Topical	50 mg
Solution	Intravenous	400 mg
Tablet, film coated	Oral	1000 MG
Tablet, coated	Oral
Solution / drops	Oral	40 mg / mL
Tablet	Oral	800 mg
Injection	Intravenous	100 MG/ML
Injection, solution	Intravenous	400 mg/4ml
Injection, solution	Intravenous	800 mg/8ml
Enema	Rectal	125 MG
Solution	Intravenous	400.000 mg
Gel	Topical	100 MG/G
Tablet, chewable	Oral	100 mg
Tablet, coated	Oral	100 mg/1
Tablet	Oral	100 mg
Tablet, coated	Oral	400 mg (titer)
Suspension	Oral	100 ml
Gel	Topical	0.5 g
Tablet		400 MG
Capsule, coated	Oral	400 mg
Capsule, coated	Oral
Solution / drops; suspension / drops		40 MG/ML
Granule, for solution	Oral	200 MG
Solution / drops	Oral	20 G/100ML
Tablet, chewable	Oral	200 MG
Tablet, effervescent	Oral	200 MG
Powder	Oral
Granule, for solution	Oral
Tablet	Oral	200 mg / tab
Tablet, film coated	Oral	100 mg/1
Tablet	Oral	800.000 mg
Kit; tablet; tablet, orally disintegrating	Oral
Capsule, liquid filled	Oral	800 mg
Tablet	Oral	350 mg
Granule, effervescent	Oral
Injection, solution	Intravenous	10 mg/1mL
Solution	Intravenous	10 mg/1mL
Capsule, liquid filled	Oral	400 mg
Suspension; syrup	Oral	100 MG/5ML
Kit; liquid; tablet	Oral; Topical
Tablet, coated		200 MG
Tablet, coated		400 MG
Tablet, orally disintegrating	Oral
Plaster	Topical
Tablet, film coated	Oral	200 mg
Capsule, liquid filled	Oral
Capsule	Oral	342 mg
Tablet	Oral	342 mg
Syrup	Oral	200 mg/5mL
Tablet, coated	Oral	30 MG
Suspension	Oral	40 MG
Suspension	Oral	20 MG
Suspension	Oral	2 %
Tablet, sugar coated	Oral	400 mg
Tablet	Oral	200.00 mg
Suspension	Oral	100 mg/1mL
Injection, solution	Intravenous
Liquid	Oral	50 mg/1.25mL
Injection, solution	Intravenous	10 mg/2ml
Tablet, sugar coated	Oral	200 mg
Kit; tablet	Oral	600 mg/1
Suspension	Oral	4000 mg
Tablet	Oral	400 mg
Tablet	Oral	400.000 mg
Tablet	Oral	400 mg/537mg
Gel	Topical	5 %
Cream	Topical	50 mg/g
Suppository	Rectal	125 mg
Tablet, coated	Oral	80000000 mg
Tablet, film coated	Oral	292.6 mg
Tablet, film coated	Oral	200 1/2001
Tablet, coated	Oral	400 mg
Tablet; tablet, film coated	Oral	400 MG
Tablet	Oral
Granule, for solution	Oral	400 mg
Solution / drops	Oral	200 MG/ML
Granule, for solution	Oral	600 MG
Granule, for suspension	Oral	400 MG
Granule, for suspension	Oral	600 MG
Patch		136 MG
Suspension	Oral	2000 mg
Suspension	Oral	4.000 g
Tablet, coated	Oral	200 mg
Kit	Oral
Cream	Topical
Kit	Oral	600 mg/1
Suspension	Oral	5 mg/ml
Tablet, effervescent	Oral
Tablet, coated	Oral
Tablet	Oral	200.000 mg
Syrup	Oral	2 g
Liquid	Oral	100 mg/5mL
Suspension / drops	Oral	50 mg/1.25mL
Suspension	Oral	2 %w/v
Suspension	Oral	20.0 mg
Tablet	Oral	400.00 mg
Syrup	Oral	100 mg/5ml
Tablet, film coated	Oral	600 mg
Tablet, film coated	Oral	400 mg
Gel	Topical	5 %w/w
Tablet, film coated	Oral	342 mg
Tablet, coated	Oral	684 mg
Tablet, coated	Oral	600 mg
Tablet, film coated	Oral	200 mg
Capsule	Oral	400 mg

Prices

Unit description	Cost	Unit
Neoprofen 20 mg/2 ml vial	304.5USD	ml
Caldolor 400 mg/4 ml vial	2.21USD	ml
Caldolor 800 mg/8 ml vial	1.58USD	ml
Nuprin arthritis patch	1.11USD	patch
Ibuprofen powder	1.04USD	g
Nuprin muscle & joint patch	1.03USD	patch
Profen II 45-800 mg 12 Hour tablet	0.69USD	tablet
Motrin 800 mg tablet	0.59USD	tablet
Advil allergy sinus caplet	0.5USD	caplet
Ibu-drops 40 mg/ml suspension drops	0.42USD	ml
Motrin 600 mg tablet	0.4USD	tablet
Ibuprofen 800 mg tablet	0.36USD	tablet
Ibuprofen 400 mg tablet	0.35USD	tablet
Infant's motrin 50 mg/1.25 ml	0.34USD	ml
Childs ibuprofen susp drp	0.33USD	ml
Ibuprofen 600 mg tablet	0.33USD	tablet
Wal-profen cold & sinus cplt	0.3USD	caplet
Infant ibuprofen susp drop	0.29USD	ml
Motrin 400 mg tablet	0.29USD	tablet
CVS Pharmacy infant ibuprofen susp drop	0.25USD	ml
Infants medi-profen susp	0.23USD	ml
Advil cold & sinus caplet	0.22USD	caplet
Advil pm caplet	0.22USD	caplet
Soba profen cold-sinus tablet	0.22USD	tablet
Midol caplet	0.21USD	caplet
Advil migraine 200 mg capsule	0.2USD	capsule
Ibuprofen cold-sinus caplet	0.2USD	caplet
Motrin 100 mg caplet	0.2USD	caplet
Motrin pm caplet	0.2USD	caplet
Advil 200 mg liqui-gel capsule	0.19USD	capsule
Soba profen ib caplet	0.19USD	caplet
Motrin 100 mg tablet chew	0.18USD	tablet
Pub infants profenib drops	0.18USD	ml
Sm ibuprofen ib 100 mg tablet	0.18USD	tablet
Eck ibuprofen jr caplet	0.17USD	caplet
Ibuprofen pm caplet	0.17USD	caplet
Advil 200 mg caplet	0.15USD	capsule
Advil 200 mg gel caplet	0.15USD	caplet
Advil 200 mg tablet	0.15USD	tablet
Ibuprofen 100 mg tablet chew	0.15USD	tablet
Motrin ib 200 mg caplet	0.15USD	caplet
Apo-Ibuprofen 600 mg Tablet	0.14USD	tablet
CVS Pharmacy ibuprofen jr str 100 mg tablet	0.14USD	tablet
Nu-Ibuprofen 600 mg Tablet	0.14USD	tablet
Motrin ib 200 mg tablet	0.13USD	tablet
Motrin ib 200 mg gelcap	0.12USD	capsule
Nuprin 200 mg caplet	0.12USD	caplet
Wal-profen 200 mg caplet	0.12USD	caplet
Wal-profen 200 mg tablet	0.12USD	tablet
Eql ibuprofen 200 mg tablet	0.1USD	tablet
Nuprin 200 mg tablet	0.1USD	tablet
Apo-Ibuprofen 400 mg Tablet	0.08USD	tablet
Ibuprofen ib 200 mg tablet	0.08USD	tablet
Novo-Profen 400 mg Tablet	0.08USD	tablet
Apo-Ibuprofen 300 mg Tablet	0.07USD	tablet
Medi-profen 200 mg tablet	0.07USD	tablet
Ibuprofen 100 mg/5ml Suspension	0.06USD	ml
Ibuprofen 200 mg caplet	0.06USD	caplet
Child ibuprofen susp	0.05USD	ml
Children's medi-profen susp	0.05USD	ml
Children's motrin cold suspension	0.05USD	ml
CVS Pharmacy ibuprofen 200 mg tablet	0.05USD	tablet
Ibuprofen cold suspension	0.05USD	ml
I-prin 200 mg tablet	0.05USD	tablet
Novo-Profen 600 mg Tablet	0.05USD	tablet
Children's motrin cold	0.04USD	ml
Pv ibuprofen 200 mg caplet	0.04USD	caplet
Soba children's profenib susp	0.04USD	ml
Ibuprofen 200 mg tablet	0.03USD	tablet
CVS Pharmacy ibuprofen 200 mg caplet	0.02USD	caplet
Pv ibuprofen 200 mg tablet	0.02USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5215755	No	1993-06-01	2010-06-01
US6599531	No	2003-07-29	2017-06-10
US6348216	No	2002-02-19	2017-06-10
US6342530	No	2002-01-29	2020-11-14
US6344479	No	2002-02-05	2021-03-20
US8415337	No	2013-04-09	2032-03-02
US6211246	No	2001-04-03	2019-06-10
US8883849	No	2014-11-11	2022-01-17
US9155718	No	2015-10-13	2022-01-17
US8263647	No	2012-09-11	2022-05-30
US7863287	No	2011-01-04	2027-02-28
US6251426	No	2001-06-26	2018-06-25
US6727286	No	2004-04-27	2021-11-27
US8735452	No	2014-05-27	2029-09-30
US9138404	No	2015-09-22	2029-09-30
US9114068	No	2015-08-25	2029-09-30
US8871810	No	2014-10-28	2029-09-30
US9012508	No	2015-04-21	2030-09-14
US9295639	No	2016-03-29	2029-09-30
US8067451	No	2011-11-29	2026-07-18
US8501228	No	2013-08-06	2026-07-18
US8318202	No	2012-11-27	2026-07-18
US8449910	No	2013-05-28	2026-07-18
US8309127	No	2012-11-13	2026-07-18
US8067033	No	2011-11-29	2026-07-18
US9649284	No	2017-05-16	2029-09-30
US9072710	No	2015-07-07	2032-03-16
US9072661	No	2015-07-07	2032-03-16
US10238640	No	2019-03-26	2024-05-25
US10532036	No	2020-01-14	2025-09-22
US11197830	No	2021-12-14	2039-02-27
US11534407	No	2019-02-27	2039-02-27
US11446266	No	2011-10-26	2031-10-26
US11806400	No	2012-03-16	2032-03-16
US11213498	No	2016-01-14	2036-01-14
US11389416	No	2015-07-17	2035-07-17
US11896567	No	2011-10-26	2031-10-26
US11918693	No	2021-07-09	2041-07-09

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	75-77.5 ºC	U.S. Patent 3,228,831 U.S. Patent 3,385,886
boiling point (°C)	157 ºC	'AlfaAesar MSDS'
water solubility	21 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	3.97	AVDEEF,A (1997)
logS	-3.99	ADME Research, USCD
Caco2 permeability	-4.28	ADME Research, USCD
pKa	5.3	Bushra and Aslam. Oman Med. 25, 3. (2010)

Predicted Properties

Property	Value	Source
Water Solubility	0.0684 mg/mL	ALOGPS
logP	3.5	ALOGPS
logP	3.84	Chemaxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.85	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	37.3 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	60.73 m³·mol^-1	Chemaxon
Polarizability	23.76 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9927
Blood Brain Barrier	+	0.9619
Caco-2 permeable	+	0.8866
P-glycoprotein substrate	Non-substrate	0.759
P-glycoprotein inhibitor I	Non-inhibitor	0.9705
P-glycoprotein inhibitor II	Non-inhibitor	0.9323
Renal organic cation transporter	Non-inhibitor	0.9323
CYP450 2C9 substrate	Non-substrate	0.7594
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.6877
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9305
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9881
CYP450 3A4 inhibitor	Non-inhibitor	0.9655
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9691
Ames test	Non AMES toxic	0.9894
Carcinogenicity	Carcinogens	0.5553
Biodegradation	Ready biodegradable	0.5142
Rat acute toxicity	2.3092 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9719
hERG inhibition (predictor II)	Non-inhibitor	0.9734

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (11.4 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	GC-MS	splash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	GC-MS	splash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	GC-MS	splash10-00di-9300000000-cc259b7768023e4cdba8
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0296-3900000000-497aad6d6a3e7af1ac0a
GC-MS Spectrum - EI-B	GC-MS	splash10-03di-3910000000-618880f8fd7b8ec3d473
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-00di-9300000000-cc259b7768023e4cdba8
Mass Spectrum (Electron Ionization)	MS	splash10-03xr-3900000000-e20ef3c30496e17720ba
MS/MS Spectrum - Quattro_QQQ 10V, N/A	LC-MS/MS	splash10-03di-0910000000-90bf6813134491c9fbfd
MS/MS Spectrum - Quattro_QQQ 25V, N/A	LC-MS/MS	splash10-001i-9800000000-56f599abc462380b648c
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	LC-MS/MS	splash10-03di-3910000000-618880f8fd7b8ec3d473
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0006-0497000000-fa397d6ffd29da116900
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0a4i-0690000000-f598b8bee69a6b62e817
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-1900000000-f1b7a986fee133d97eb1
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-0920000000-aa36b3244e32560bb9d5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1930000000-728a67daaea8ecb1b60a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-e8049d9759b81f0d56b0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05mo-5900000000-3c32234af86d6b3a2656
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-02ai-0900000000-e1c07c4d6d5219e98219
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0ldl-4900000000-7635978e2602fb36e1ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0900000000-b1bbd0cff6f4f6df9ebc
1H NMR Spectrum	1D NMR	Not Applicable
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	161.798312	predicted	DarkChem Lite v0.1.0
[M-H]-	145.04115	predicted	DeepCCS 1.0 (2019)
[M+H]+	148.78854	predicted	DeepCCS 1.0 (2019)
[M+Na]+	157.5005	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	8000	N/A	N/A	A27774
IC 50 (nM)	100	N/A	N/A	A27777
IC 50 (nM)	30000	N/A	N/A	A29389 / A29390 / A29391
IC 50 (nM)	1030000	N/A	N/A	A27759
IC 50 (nM)	6200	N/A	N/A	A29388
IC 50 (nM)	1100	N/A	N/A	A28402 / A29236 / A28406 / A29392 / A28407 / A28413 / A27813 / A28423
IC 50 (nM)	80000	N/A	N/A	A27805 / A27812
IC 50 (nM)	1400	N/A	N/A	A27808
IC 50 (nM)	730	N/A	N/A	A29393
IC 50 (nM)	1350	N/A	N/A	A29394
IC 50 (nM)	36000	N/A	N/A	A29075
Ki (nM)	9900	N/A	N/A	A5629
Ki (nM)	7200	N/A	N/A	A27471
Ki (nM)	>10000	N/A	N/A	A27471 / A27790

Details1. Prostaglandin G/H synthase 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity).
Specific Function: enzyme binding
Gene Name: PTGS2
Uniprot ID: P35354
Uniprot Name: Prostaglandin G/H synthase 2
Molecular Weight: 68995.625 Da

References

Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [Article]
Ouellet M, Falgueyret JP, Percival MD: Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms. Biochem J. 2004 Feb 1;377(Pt 3):675-84. [Article]
Gallego-Sandin S, Novalbos J, Rosado A, Gisbert JP, Galvez-Mugica MA, Garcia AG, Pajares JM, Abad-Santos F: Effect of ibuprofen on cyclooxygenase and nitric oxide synthase of gastric mucosa: correlation with endoscopic lesions and adverse reactions. Dig Dis Sci. 2004 Sep;49(9):1538-44. [Article]
Murphey LJ, Williams MK, Sanchez SC, Byrne LM, Csiki I, Oates JA, Johnson DH, Morrow JD: Quantification of the major urinary metabolite of PGE2 by a liquid chromatographic/mass spectrometric assay: determination of cyclooxygenase-specific PGE2 synthesis in healthy humans and those with lung cancer. Anal Biochem. 2004 Nov 15;334(2):266-75. [Article]
Sanchez-Fidalgo S, Martin-Lacave I, Illanes M, Motilva V: Angiogenesis, cell proliferation and apoptosis in gastric ulcer healing. Effect of a selective cox-2 inhibitor. Eur J Pharmacol. 2004 Nov 28;505(1-3):187-94. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. C-X-C chemokine receptor type 2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Receptor for interleukin-8 which is a powerful neutrophil chemotactic factor (PubMed:1891716). Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system (PubMed:8662698). Binds to IL-8 with high affinity. Also binds with high affinity to CXCL3, GRO/MGSA and NAP-2.
Specific Function: C-C chemokine binding
Gene Name: CXCR2
Uniprot ID: P25025
Uniprot Name: C-X-C chemokine receptor type 2
Molecular Weight: 40758.735 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details3. Interleukin-8

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Chemotactic factor that mediates inflammatory response by attracting neutrophils, basophils, and T-cells to clear pathogens and protect the host from infection (PubMed:18692776, PubMed:7636208). Also plays an important role in neutrophil activation (PubMed:2145175, PubMed:9623510). Released in response to an inflammatory stimulus, exerts its effect by binding to the G-protein-coupled receptors CXCR1 and CXCR2, primarily found in neutrophils, monocytes and endothelial cells (PubMed:1840701, PubMed:1891716). G-protein heterotrimer (alpha, beta, gamma subunits) constitutively binds to CXCR1/CXCR2 receptor and activation by IL8 leads to beta and gamma subunits release from Galpha (GNAI2 in neutrophils) and activation of several downstream signaling pathways including PI3K and MAPK pathways (PubMed:11971003, PubMed:8662698).
Specific Function: chemokine activity
Gene Name: CXCL8
Uniprot ID: P10145
Uniprot Name: Interleukin-8
Molecular Weight: 11097.98 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details4. C-X-C chemokine receptor type 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Receptor to interleukin-8, which is a powerful neutrophils chemotactic factor (PubMed:1840701). Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system (PubMed:8662698).
Specific Function: C-C chemokine binding
Gene Name: CXCR1
Uniprot ID: P25024
Uniprot Name: C-X-C chemokine receptor type 1
Molecular Weight: 39790.735 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	18000	N/A	N/A	A27759
IC 50 (nM)	6900	N/A	N/A	A29388

Details5. Prostaglandin G/H synthase 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity).
Specific Function: heme binding
Gene Name: PTGS1
Uniprot ID: P23219
Uniprot Name: Prostaglandin G/H synthase 1
Molecular Weight: 68685.82 Da

References

Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [Article]
Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [Article]
Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [Article]
Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [Article]
Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [Article]

Details6. Apoptosis regulator Bcl-2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Modulator

General Function: Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785).
Specific Function: BH domain binding
Gene Name: BCL2
Uniprot ID: P10415
Uniprot Name: Apoptosis regulator Bcl-2
Molecular Weight: 26265.66 Da

References

Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]

Details7. Thrombomodulin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin generated.
Specific Function: calcium ion binding
Gene Name: THBD
Uniprot ID: P07204
Uniprot Name: Thrombomodulin
Molecular Weight: 60328.72 Da

References

Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]

Details8. Fatty acid-binding protein, intestinal

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: FABPs are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long-chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor.
Specific Function: fatty acid binding
Gene Name: FABP2
Uniprot ID: P12104
Uniprot Name: Fatty acid-binding protein, intestinal
Molecular Weight: 15237.195 Da

References

Velkov T, Chuang S, Wielens J, Sakellaris H, Charman WN, Porter CJ, Scanlon MJ: The interaction of lipophilic drugs with intestinal fatty acid-binding protein. J Biol Chem. 2005 May 6;280(18):17769-76. Epub 2005 Feb 18. [Article]

Details9. Peroxisome proliferator-activated receptor gamma

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Activator

General Function: Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity).
Specific Function: alpha-actinin binding
Gene Name: PPARG
Uniprot ID: P37231
Uniprot Name: Peroxisome proliferator-activated receptor gamma
Molecular Weight: 57619.58 Da

References

Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [Article]

Details10. Cystic fibrosis transmembrane conductance regulator

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Epithelial ion channel that plays an important role in the regulation of epithelial ion and water transport and fluid homeostasis (PubMed:26823428). Mediates the transport of chloride ions across the cell membrane (PubMed:10792060, PubMed:11524016, PubMed:11707463, PubMed:12519745, PubMed:12529365, PubMed:12588899, PubMed:12727866, PubMed:15010471, PubMed:17036051, PubMed:1712898, PubMed:17182731, PubMed:19398555, PubMed:19621064, PubMed:22178883, PubMed:25330774, PubMed:26846474, PubMed:28087700, PubMed:8910473, PubMed:9804160). Possesses an intrinsic ATPase activity and utilizes ATP to gate its channel; the passive flow of anions through the channel is gated by cycles of ATP binding and hydrolysis by the ATP-binding domains (PubMed:11524016, PubMed:15284228, PubMed:26627831, PubMed:8910473). The ion channel is also permeable to HCO(3)(-); selectivity depends on the extracellular chloride concentration (PubMed:15010471, PubMed:19019741). In vitro, mediates ATP-dependent glutathione flux (PubMed:12727866). Exerts its function also by modulating the activity of other ion channels and transporters (PubMed:12403779, PubMed:22121115, PubMed:22178883, PubMed:27941075). Plays an important role in airway fluid homeostasis (PubMed:16645176, PubMed:19621064, PubMed:26823428). Contributes to the regulation of the pH and the ion content of the airway surface fluid layer and thereby plays an important role in defense against pathogens (PubMed:14668433, PubMed:16645176, PubMed:26823428). Modulates the activity of the epithelial sodium channel (ENaC) complex, in part by regulating the cell surface expression of the ENaC complex (PubMed:17182731, PubMed:17434346, PubMed:27941075). Inhibits the activity of the ENaC channel containing subunits SCNN1A, SCNN1B and SCNN1G (PubMed:17182731). Inhibits the activity of the ENaC channel containing subunits SCNN1D, SCNN1B and SCNN1G, but not of the ENaC channel containing subunits SCNN1A, SCNN1B and SCNN1G (PubMed:17182731, PubMed:27941075). May regulate bicarbonate secretion and salvage in epithelial cells by regulating the transporter SLC4A7 (PubMed:12403779). Can inhibit the chloride channel activity of ANO1 (PubMed:22178883). Plays a role in the chloride and bicarbonate homeostasis during sperm epididymal maturation and capacitation (PubMed:19923167, PubMed:27714810).
Specific Function: ABC-type transporter activity
Gene Name: CFTR
Uniprot ID: P13569
Uniprot Name: Cystic fibrosis transmembrane conductance regulator
Molecular Weight: 168139.895 Da

References

Devor DC, Schultz BD: Ibuprofen inhibits cystic fibrosis transmembrane conductance regulator-mediated Cl- secretion. J Clin Invest. 1998 Aug 15;102(4):679-87. [Article]

Details11. Peroxisome proliferator-activated receptor alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Activator

General Function: Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as a transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Specific Function: DNA binding
Gene Name: PPARA
Uniprot ID: Q07869
Uniprot Name: Peroxisome proliferator-activated receptor alpha
Molecular Weight: 52224.595 Da

References

Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [Article]

Details12. Platelet glycoprotein Ib alpha chain

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: GP-Ib, a surface membrane protein of platelets, participates in the formation of platelet plugs by binding to the A1 domain of vWF, which is already bound to the subendothelium.
Specific Function: thrombin-activated receptor activity
Gene Name: GP1BA
Uniprot ID: P07359
Uniprot Name: Platelet glycoprotein Ib alpha chain
Molecular Weight: 71539.265 Da

References

Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]

Details13. Protein S100-A7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Not Available
Specific Function: calcium ion binding
Gene Name: S100A7
Uniprot ID: P31151
Uniprot Name: Protein S100-A7
Molecular Weight: 11470.87 Da

References

Fujiwara R, Takenaka S, Hashimoto M, Narawa T, Itoh T: Expression of human solute carrier family transporters in skin: possible contributor to drug-induced skin disorders. Sci Rep. 2014 Jun 11;4:5251. doi: 10.1038/srep05251. [Article]

Enzymes

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	50000	N/A	N/A	A27494

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031).
Specific Function: (R)-limonene 6-monooxygenase activity
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Carlile DJ, Hakooz N, Bayliss MK, Houston JB: Microsomal prediction of in vivo clearance of CYP2C9 substrates in humans. Br J Clin Pharmacol. 1999 Jun;47(6):625-35. [Article]
Flockhart Table of Drug Interactions [Link]
FDA label, Ibuprofen [File]

Details2. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316).
Specific Function: arachidonic acid epoxygenase activity
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [Article]
Chang SY, Li W, Traeger SC, Wang B, Cui D, Zhang H, Wen B, Rodrigues AD: Confirmation that cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(-)-ibuprofen hydroxylation in vitro. Drug Metab Dispos. 2008 Dec;36(12):2513-22. doi: 10.1124/dmd.108.022970. Epub 2008 Sep 11. [Article]
Hamman MA, Thompson GA, Hall SD: Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. Biochem Pharmacol. 1997 Jul 1;54(1):33-41. doi: 10.1016/s0006-2952(97)00143-3. [Article]

Details3. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307).
Specific Function: (R)-limonene 6-monooxygenase activity
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55944.565 Da

References

Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]
Goldstein JA: Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55. [Article]
Mazaleuskaya LL, Theken KN, Gong L, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106. doi: 10.1097/FPC.0000000000000113. [Article]

Details4. UDP-glucuronosyltransferase 1A3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Isoform 1 UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:18674515, PubMed:18719240, PubMed:23288867, PubMed:23756265, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:23756265). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229, PubMed:18719240, PubMed:23288867). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3, essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonists losartan, candesartan and zolarsartan, which can inhibit the effect of angiotensin II (PubMed:18674515).
Specific Function: enzyme binding
Gene Name: UGT1A3
Uniprot ID: P35503
Uniprot Name: UDP-glucuronosyltransferase 1A3
Molecular Weight: 60337.835 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details5. UDP-glucuronosyltransferase 1A9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Isoform 1 UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212).
Specific Function: enzyme binding
Gene Name: UGT1A9
Uniprot ID: O60656
Uniprot Name: UDP-glucuronosyltransferase 1A9
Molecular Weight: 59940.495 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details6. UDP-glucuronosyltransferase 2B4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18719240, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18719240, PubMed:23288867). Catalyzes the glucuronidation of the endogenous estrogen hormones such as estradiol and estriol (PubMed:18719240, PubMed:23288867).
Specific Function: glucuronosyltransferase activity
Gene Name: UGT2B4
Uniprot ID: P06133
Uniprot Name: UDP-glucuronosyltransferase 2B4
Molecular Weight: 60512.035 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details7. UDP-glucuronosyltransferase 2B7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161).
Specific Function: glucuronosyltransferase activity
Gene Name: UGT2B7
Uniprot ID: P16662
Uniprot Name: UDP-glucuronosyltransferase 2B7
Molecular Weight: 60720.15 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details8. Alpha-methylacyl-CoA racemase

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Not Available
Specific Function: catalytic activity
Gene Name: AMACR
Uniprot ID: D6RB81
Uniprot Name: Alpha-methylacyl-CoA racemase
Molecular Weight: 40674.37 Da

References

Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]

Details9. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981).
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Mazaleuskaya LL, Theken KN, Gong L, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106. doi: 10.1097/FPC.0000000000000113. [Article]

Carriers

Details1. Albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017).
Specific Function: antioxidant activity
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Albumin
Molecular Weight: 69365.94 Da

References

Yamasaki K, Rahman MH, Tsutsumi Y, Maruyama T, Ahmed S, Kragh-Hansen U, Otagiri M: Circular dichroism simulation shows a site-II-to-site-I displacement of human serum albumin-bound diclofenac by ibuprofen. AAPS PharmSciTech. 2000 May 14;1(2):E12. [Article]
Galantini L, Leggio C, Konarev PV, Pavel NV: Human serum albumin binding ibuprofen: a 3D description of the unfolding pathway in urea. Biophys Chem. 2010 Apr;147(3):111-22. doi: 10.1016/j.bpc.2010.01.002. Epub 2010 Jan 18. [Article]

Transporters

Details1. Solute carrier organic anion transporter family member 2B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927).
Specific Function: bile acid transmembrane transporter activity
Gene Name: SLCO2B1
Uniprot ID: O94956
Uniprot Name: Solute carrier organic anion transporter family member 2B1
Molecular Weight: 76697.93 Da

References

Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [Article]

Details2. ATP-dependent translocase ABCB1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218).
Specific Function: ABC-type xenobiotic transporter activity
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: ATP-dependent translocase ABCB1
Molecular Weight: 141477.255 Da

References

Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [Article]

Details3. ATP-binding cassette sub-family C member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685).
Specific Function: 15-hydroxyprostaglandin dehydrogenase (NAD+) activity
Gene Name: ABCC4
Uniprot ID: O15439
Uniprot Name: ATP-binding cassette sub-family C member 4
Molecular Weight: 149525.33 Da

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]

Details4. Multidrug resistance-associated protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Mediates export of organic anions and drugs from the cytoplasm (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:9281595). Hydrolyzes ATP with low efficiency (PubMed:16230346). Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (PubMed:17050692). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity). Mediates ATP-dependent, GSH-independent cyclic GMP-AMP (cGAMP) export (PubMed:36070769). Thus, by limiting intracellular cGAMP concentrations negatively regulates the cGAS-STING pathway (PubMed:36070769).
Specific Function: ABC-type glutathione S-conjugate transporter activity
Gene Name: ABCC1
Uniprot ID: P33527
Uniprot Name: Multidrug resistance-associated protein 1
Molecular Weight: 171589.5 Da

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]

Details5. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable).
Specific Function: bile acid transmembrane transporter activity
Gene Name: SLCO1A2
Uniprot ID: P46721
Uniprot Name: Solute carrier organic anion transporter family member 1A2
Molecular Weight: 74144.105 Da

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	8000	N/A	N/A	A16280

Details6. Solute carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651).
Specific Function: alpha-ketoglutarate transmembrane transporter activity
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: Solute carrier family 22 member 6
Molecular Weight: 61815.78 Da

References

Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [Article]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [Article]
Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1170000	N/A	N/A	A6155

Details7. Organic anion transporter 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity).
Specific Function: organic anion transmembrane transporter activity
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Organic anion transporter 3
Molecular Weight: 59855.585 Da

References

Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [Article]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]

Details8. Solute carrier family 22 member 11

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Antiporter that mediates the transport of conjugated steroids and other specific organic anions at the basal membrane of syncytiotrophoblast and at the apical membrane of proximal tubule epithelial cells, in exchange for anionic compounds (PubMed:10660625, PubMed:11907186, PubMed:15037815, PubMed:15102942, PubMed:15291761, PubMed:15576633, PubMed:17229912, PubMed:18501590, PubMed:26277985, PubMed:28027879). May be responsible for placental absorption of fetal-derived steroid sulfates such as estrone sulfate (E1S) and the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S), as well as clearing waste products and xenobiotics from the fetus (PubMed:12409283). Maybe also be involved in placental urate homeostasis (PubMed:17229912). Facilitates the renal reabsorption of organic anions such as urate and derived steroid sulfates (PubMed:15037815, PubMed:17229912). Organic anion glutarate acts as conteranion for E1S renal uptake (PubMed:15037815, PubMed:17229912). Possible transport mode may also include DHEA-S/E1S exchange (PubMed:28027879). Also interacts with inorganic anions such as chloride and hydroxyl ions, therefore possible transport modes may include E1S/Cl(-), E1S/OH(-), urate/Cl(-) and urate/OH(-) (PubMed:17229912). Also mediates the transport of prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may be involved in their renal excretion (PubMed:11907186). Also able to uptake anionic drugs, diuretics, bile salts and ochratoxin A (PubMed:10660625, PubMed:26277985). Mediates the unidirectional efflux of glutamate and aspartate (PubMed:28027879). Glutamate efflux down its transmembrane gradient may drive SLC22A11/OAT4-mediated placental uptake of E1S (PubMed:26277985).
Specific Function: organic anion transmembrane transporter activity
Gene Name: SLC22A11
Uniprot ID: Q9NSA0
Uniprot Name: Solute carrier family 22 member 11
Molecular Weight: 59970.945 Da

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 27, 2024 07:15

Ibuprofen

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Structure for Ibuprofen (DB01050)

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