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Identification
- Summary
Esomeprazole is a proton pump inhibitor used to treat GERD, reduce the risk of NSAID associated gastric ulcers, eradicate H. pylori, and to treat conditions causing gastric acid hypersecretion.
- Brand Names
- Nexium, Vimovo
- Generic Name
- Esomeprazole
- DrugBank Accession Number
- DB00736
- Background
Esomeprazole, sold under the brand name Nexium, is a proton pump inhibitor (PPI) medication used for the management of gastroesophageal reflux disease (GERD), for gastric protection to prevent recurrence of stomach ulcers or gastric damage from chronic use of NSAIDs, and for the treatment of pathological hypersecretory conditions including Zollinger-Ellison (ZE) Syndrome. It can also be found in quadruple regimens for the treatment of H. pylori infections along with other antibiotics including Amoxicillin, Clarithromycin, and Metronidazole, for example.7,10 Its efficacy is considered similar to other medications within the PPI class including Omeprazole, Pantoprazole, Lansoprazole, Dexlansoprazole, and Rabeprazole. Esomeprazole is the s-isomer of Omeprazole, which is a racemate of the S- and R-enantiomer. Esomeprazole has been shown to inhibit acid secretion to a similar extent as Omeprazole, without any significant differences between the two compounds in vitro.
Esomeprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of esomeprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, esomeprazole's duration of antisecretory effect persists longer than 24 hours.Label
PPIs such as esomeprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.3,4
Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as esomeprazole has been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients such as iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.5
Rapid discontinuation of PPIs such as esomeprazole may cause a rebound effect and a short term increase in hypersecretion.6 Esomeprazole doses should be slowly lowered, or tapered, before discontinuing to prevent this rebound effect.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Esomeprazole (DB00736)
- Weight
- Average: 345.416
Monoisotopic: 345.114712179 - Chemical Formula
- C17H19N3O3S
- Synonyms
- (−)-omeprazole
- (S)-(−)-omeprazole
- (S)-omeprazole
- Esomeprazol
- Ésoméprazole
- Esomeprazole
- Esomeprazolum
- Omeprazole S-form
- Perprazole
- External IDs
- A02BC05
- H 199/18
Pharmacology
- Indication
Esomeprazole is indicated for the treatment of acid-reflux disorders including healing and maintenance of erosive esophagitis, and symptomatic gastroesophageal reflux disease (GERD), peptic ulcer disease, H. pylori eradication, prevention of gastrointestinal bleeds with NSAID use, and for the long-term treatment of pathological hypersecretory conditions including Zollinger-Ellison Syndrome.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Duodenal ulcer Combination Product in combination with: Sodium bicarbonate (DB01390) •••••••••••• •••••• Treatment of Erosive esophagitis •••••••••••• Used in combination to manage Erosive esophagitis (ee) Combination Product in combination with: Sodium bicarbonate (DB01390) •••••••••••• •••••• Used in combination for symptomatic treatment of Erosive esophagitis (ee) Combination Product in combination with: Sodium bicarbonate (DB01390) •••••••••••• •••••• Management of Gerd •••••••••••• - Contraindications & Blackbox Warnings
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Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. By doing so, it inhibits acid secretion into the gsatric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
Esomeprazole is the s-isomer of Omeprazole, which is a racemate of the S- and R-enantiomer. Esomeprazole has been shown to inhibit acid secretion to a similar extent as Omeprazole, without any significant differences between the two compounds in vitro.
PPIs such as esomeprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.3,4
Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as esomeprazole has been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients including iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.5
- Mechanism of action
Esomeprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of esomeprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, esomeprazole's duration of antisecretory effect that persists longer than 24 hours.Label
Target Actions Organism APotassium-transporting ATPase alpha chain 1 inhibitorHumans APotassium-transporting ATPase subunit beta modulatorHumans UN(G),N(G)-dimethylarginine dimethylaminohydrolase 1 Not Available Humans - Absorption
After oral administration, peak plasma levels (Cmax) occur at approximately 1.5 hours (Tmax). The Cmax increases proportionally when the dose is increased, and there is a three-fold increase in the area under the plasma concentration-time curve (AUC) from 20 to 40 mg. At repeated once-daily dosing with 40 mg, the systemic bioavailability is approximately 90% compared to 64% after a single dose of 40 mg. The mean exposure (AUC) to esomeprazole increases from 4.32 μmolhr/L on Day 1 to 11.2 μmolhr/L on Day 5 after 40 mg once daily dosing. The AUC after administration of a single 40 mg dose of Esomeprazole is decreased by 43% to 53% after food intake compared to fasting conditions. Esomeprazole should be taken at least one hour before meals.Label
Combination Therapy with Antimicrobials:
Esomeprazole magnesium 40 mg once daily was given in combination with Clarithromycin 500 mg twice daily and Amoxicillin 1000 mg twice daily for 7 days to 17 healthy male and female subjects. The mean steady state AUC and Cmax of esomeprazole increased by 70% and 18%, respectively during triple combination therapy compared to treatment with esomeprazole alone. The observed increase in esomeprazole exposure during co-administration with clarithromycin and amoxicillin is not expected to produce significant safety concerns.
- Volume of distribution
The apparent volume of distribution at steady state in healthy volunteers is approximately 16 L.Label
- Protein binding
Esomeprazole is 97% bound to plasma proteins. Plasma protein binding is constant over the concentration range of 2 to 20 µmol/L.Label
- Metabolism
Esomeprazole is extensively metabolized in the liver by the cytochrome P450 (CYP) enzyme system. The metabolites of esomeprazole lack antisecretory activity. The major part of esomeprazole’s metabolism is dependent upon the CYP2C19 isoenzyme, which forms the hydroxy and desmethyl metabolites. The remaining amount is dependent on CYP3A4 which forms the sulphone metabolite. CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15 to 20% of Asians lack CYP2C19 and are termed Poor Metabolizers.Label However, the influence of CYP 2C19 polymorphism is less pronounced for esomeprazole than for omeprazole.9 At steady state, the ratio of AUC in Poor Metabolizers to AUC in the rest of the population (Extensive Metabolizers) is approximately 2.
Following administration of equimolar doses, the S- and R-isomers are metabolized differently by the liver, resulting in higher plasma levels of the S- than of the R-isomer.Label
Nine major urinary metabolites have been detected. The two main metabolites have been identified as hydroxyesomeprazole and the corresponding carboxylic acid. Three major metabolites have been identified in plasma: the 5-O-desmethyl- and sulphone derivatives and hydroxyesomeprazole. The major metabolites of esomeprazole have no effect on gastric acid secretion.9
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- Route of elimination
The plasma elimination half-life of esomeprazole is approximately 1 to 1.5 hours. Less than 1% of parent drug is excreted in the urine. Approximately 80% of an oral dose of esomeprazole is excreted as inactive metabolites in the urine, and the remainder is found as inactive metabolites in the feces.
- Half-life
1-1.5 hours
- Clearance
Not Available
- Adverse Effects
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Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating
- Pathways
Pathway Category Esomeprazole Metabolism Pathway Drug metabolism Esomeprazole Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYP2C19*2 (A;A) A Allele, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of esomeprazole. Details Cytochrome P450 2C19 CYP2C19*3 (A;A) A Allele, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of esomeprazole. Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Poor metabolizer, lower dose requirement, improved drug efficacy Details
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 Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Esomeprazole can be increased when it is combined with Abametapir. Abatacept The metabolism of Esomeprazole can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Esomeprazole. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Esomeprazole. Acyclovir The excretion of Acyclovir can be decreased when combined with Esomeprazole. - Food Interactions
- Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Esomeprazole magnesium 925R0D7W1O 161973-10-0 KWORUUGOSLYAGD-YPPDDXJESA-N Esomeprazole magnesium dihydrate 36H71644EQ 217087-10-0 DBOUSUONOXEWHU-VCKZSRROSA-N Esomeprazole magnesium trihydrate R6DXU4WAY9 217087-09-7 VEVZQDGATGBLIC-UHFFFAOYSA-N Esomeprazole sodium L2C9GWQ43H 161796-78-7 RYXPMWYHEBGTRV-JIDHJSLPSA-N Esomeprazole strontium SCC2RK476A 914613-86-8 FEVPVZSYBDUVGY-YPPDDXJESA-N Esomeprazole strontium hydrate C5N25H3803 934714-36-0 NCGHIAKEJNQSMS-QLGOZJDFSA-N - Product Images
- International/Other Brands
- Alenia (Delta) / Awa-Block (Usawa) / Axagon (Simesa) / Cor (Prater) / Cronopep (Biotoscana) / Emanera (Krka) / Emep (Aristopharma) / Emozul (HYGIA) / ES-OD (Piramal Healthcare) / Esmep (HYGIA) / Eso (Asiatic Lab) / Esofag (Micro Labs) / Esolok (Ibn Sina) / Esomarfan (Marfan) / Esomenta (RAK) / Esomep (ACI) / Esomeprazol Genfar (Genfar S.A) / Esopral (Maquifarma) / Esorest (Centaur) / Inexium paranova / Lucen (Malesci) / Nexiam (AstraZeneca)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Esomeprazole Tablet, delayed release 40 mg Oral Sanis Health Inc 2014-09-22 Not applicable Canada 
Esomeprazole Tablet, delayed release 40 mg Oral Ethypharm Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral TEVA Canada Limited Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral Sanis Health Inc 2024-03-20 Not applicable Canada Esomeprazole Tablet, delayed release 40 mg Oral Sivem Pharmaceuticals Ulc 2015-07-22 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-esomeprazole Tablet, delayed release 40 mg Oral Apotex Corporation 2011-03-07 Not applicable Canada Apo-esomeprazole Tablet, delayed release 20 mg Oral Apotex Corporation 2012-03-02 Not applicable Canada Esomeprazole DR Capsule, delayed release 20 mg/1 Oral Direct_Rx 2022-09-13 Not applicable US 
Esomeprazole Magneisum D/r Capsule, delayed release 40 mg/1 Oral Direct_Rx 2019-06-04 Not applicable US Esomeprazole Magnesium Capsule, delayed release 40 mg/1 Oral Unit Dose Services 2015-02-17 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acid Reducer Tablet, delayed release 20 mg/1 Oral CVS PHARMACY 2021-12-31 Not applicable US Acid Reducer Tablet, delayed release 20 mg/1 Oral Rite Aid Corporation 2021-07-23 Not applicable US Acid Reducer Tablet, delayed release 20 mg/1 Oral H E B 2022-03-31 Not applicable US Acid Reducer Tablet, delayed release 20 mg/1 Oral Cardinal Health (Leader) 70000 2021-04-30 Not applicable US Acid Reducer Tablet, delayed release 20 mg/1 Oral P & L Development, LLC 2020-12-31 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Anodyne Ile Esomeprazole magnesium trihydrate (40 mg/1) + Ibuprofen (100 mg/5mL) + Levomenthol (1 g/100g) + Lidocaine (4 g/100g) Kit Oral; Topical Fortus Pharma, Llc 2017-10-16 2018-08-27 US CHRYSTELLE Esomeprazole magnesium dihydrate (0.02 MG) + Estradiol (3 MG) Tablet, film coated Eg S.P.A. 2014-07-08 Not applicable Italy 
ESOVIP 20/1680 MG TOZ İÇEREN SAŞE, 14 ADET Esomeprazole (20 mg) + Sodium bicarbonate (1680 mg) Powder Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2012-11-22 Not applicable Turkey 
ESOVIP 20/1680 MG TOZ İÇEREN SAŞE, 28 ADET Esomeprazole (20 mg) + Sodium bicarbonate (1680 mg) Powder Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2012-11-22 Not applicable Turkey Mylan-naproxen/esomeprazole Mr Esomeprazole magnesium (20 mg) + Naproxen (375 mg) Tablet, delayed release Oral Mylan Pharmaceuticals 2017-02-27 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image PharmapureRx ESOMEP-EZS Esomeprazole magnesium dihydrate (20 mg/1) Kit Oral PureTek Corporation 2017-07-26 2021-05-31 US
Categories
- ATC Codes
- A02BD06 — Esomeprazole, amoxicillin and clarithromycin
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BC — Proton pump inhibitors
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- 2-Pyridinylmethylsulfinylbenzimidazoles
- Acid Reducers
- Alimentary Tract and Metabolism
- Anti-Ulcer Agents
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Benzimidazoles
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Enzyme Inhibitors
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Heterocyclic Compounds, Fused-Ring
- Musculo-Skeletal System
- OAT3/SLC22A8 Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Photosensitizing Agents
- Propionates
- Proton Pump Inhibitors
- Proton-pump Inhibitors
- Pyridines
- Sulfoxides
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzimidazoles
- Sub Class
- Sulfinylbenzimidazoles
- Direct Parent
- Sulfinylbenzimidazoles
- Alternative Parents
- Anisoles / Methylpyridines / Alkyl aryl ethers / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- N3PA6559FT
- CAS number
- 119141-88-7
- InChI Key
- SUBDBMMJDZJVOS-DEOSSOPVSA-N
- InChI
- InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1
- IUPAC Name
- 5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
- SMILES
- COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1
References
- Synthesis Reference
Manne Reddy, "Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof." U.S. Patent US20040167173, issued August 26, 2004.
US20040167173- General References
- Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. [Article]
- Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. [Article]
- Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [Article]
- Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [Article]
- Haastrup PF, Thompson W, Sondergaard J, Jarbol DE: Side Effects of Long-Term Proton Pump Inhibitor Use: A Review. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):114-121. doi: 10.1111/bcpt.13023. Epub 2018 May 24. [Article]
- Reimer C, Sondergaard B, Hilsted L, Bytzer P: Proton-pump inhibitor therapy induces acid-related symptoms in healthy volunteers after withdrawal of therapy. Gastroenterology. 2009 Jul;137(1):80-7, 87.e1. doi: 10.1053/j.gastro.2009.03.058. Epub 2009 Apr 10. [Article]
- Fallone CA, Chiba N, van Zanten SV, Fischbach L, Gisbert JP, Hunt RH, Jones NL, Render C, Leontiadis GI, Moayyedi P, Marshall JK: The Toronto Consensus for the Treatment of Helicobacter pylori Infection in Adults. Gastroenterology. 2016 Jul;151(1):51-69.e14. doi: 10.1053/j.gastro.2016.04.006. Epub 2016 Apr 19. [Article]
- DailyMed Label: NEXIUM (esomeprazole magnesium) delayed-release capsules or granules, for oral use [Link]
- Health Canada Label - Esomeprazole [File]
- TOP Guidelines - H pylori [File]
- External Links
- Human Metabolome Database
- HMDB0005009
- KEGG Drug
- D07917
- PubChem Compound
- 9568614
- PubChem Substance
- 46504894
- ChemSpider
- 7843323
- 283742
- ChEBI
- 50275
- ChEMBL
- CHEMBL1201320
- ZINC
- ZINC000004693574
- Therapeutic Targets Database
- DCL000524
- PharmGKB
- PA10075
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Esomeprazole
- FDA label
- Download (1.02 MB)
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 dataNot Available Completed Not Available Calcium Metabolism Disorders 1 somestatus stop reason just information to hide Not Available Completed Not Available Community Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Gastro-esophageal Reflux Disease (GERD) / Quality of Life (QOL) 1 somestatus stop reason just information to hide Not Available Completed Not Available Gastroesophageal Reflux 1 somestatus stop reason just information to hide Not Available Completed Not Available Helicobacter Pylori 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Astrazeneca lp
- Packagers
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- AstraZeneca Inc.
- Cardinal Health
- Direct Pharmaceuticals Inc.
- Diversified Healthcare Services Inc.
- Innoviant Pharmacy Inc.
- Lake Erie Medical and Surgical Supply
- Merck & Co.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Prepackage Specialists
- Rebel Distributors Corp.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Dosage Forms
Form Route Strength Capsule Oral 40.00 mg Capsule Oral 22.250 mg Kit Oral; Topical Injection, powder, for solution 40 MG Tablet, film coated Tablet, coated Oral 20 mg Capsule, delayed release pellets Oral 20 mg Capsule, delayed release pellets Oral 40 mg Capsule Oral 20 mg Capsule Oral 40 mg Powder Intravenous 40 mg/1vial Powder Intravenous 40 mg Powder, for solution Intravenous 40 mg Tablet Oral Capsule, delayed release Oral 22.25 MG Capsule, delayed release Oral 44.5 MG Tablet, delayed release Oral 22.545 MG Tablet, delayed release Oral 45.09 MG Capsule, coated pellets Oral 20 mg Capsule, coated pellets Oral 40 mg Injection Intravenous 40 mg Capsule, coated Oral 4000000 mg Capsule, coated Oral 2000000 mg Granule Oral 5 mg Injection Intravenous Tablet, delayed release Oral 20 mg Tablet, delayed release Oral 40 mg Tablet, delayed release Oral 4000000 mg Injection, powder, for solution Parenteral Tablet, delayed release Oral Tablet, coated Oral 2000000 mg Capsule Oral 20 mg/1 Tablet, delayed release Oral 20 mg/1 Tablet, orally disintegrating, delayed release Oral 20 mg/1 Capsule, coated pellets Oral 20 mg/1 Capsule, coated pellets Oral 40 mg/1 Capsule, delayed release Oral 40 1/1 Capsule, delayed release pellets Oral 20 mg/1 Capsule, delayed release pellets Oral 40 mg/1 For suspension Oral 20 mg/1 For suspension Oral 40 mg/1 Granule, for suspension, extended release Oral 10 mg/1 Injection, powder, for solution Intravenous 40 mg Injection Intravenous 40 mg/5mL Injection, powder, for solution 40 MG/ML Injection, powder, for solution Intravenous 40 mg/5ml Injection, powder, for solution; injection, powder, lyophilized, for solution Intravenous 40 mg Injection, powder, lyophilized, for solution Intravenous 120 mg Injection, powder, lyophilized, for solution Intravenous 20 mg/5mL Injection, powder, lyophilized, for solution Intravenous 20 mg/1 Injection, powder, lyophilized, for solution Intravenous 40 mg/1 Injection, powder, lyophilized, for solution Intravenous 40 mg/5mL Capsule, delayed release Oral 24.65 mg/1 Capsule, delayed release Oral 49.3 mg/1 Tablet Oral 40 MG Capsule, delayed release Oral Powder, for solution Parenteral 40 MG Tablet, delayed release Oral 22.21 mg Capsule, coated Oral 20 mg Capsule Oral Powder Oral Injection, powder, lyophilized, for solution Intravenous 40 mg Tablet, coated Oral 20.00 mg Tablet, coated Oral 40.00 mg Injection, powder, for solution Tablet, film coated Oral 20 mg Tablet, delayed release Oral 22.264 Mg Tablet, delayed release Oral 44.528 Mg Capsule, coated Oral 41.2 mg Capsule, coated Oral 40 mg Tablet, coated Oral 40 mg Granule Oral 10 MG Injection, powder, for solution Parenteral 40 MG Solution Intravenous 42.533 mg Tablet Oral 41.400 mg Granule Oral 2.500 mg Tablet Oral 20.000 mg Tablet, film coated Oral Granule Oral 2.5 mg Granule Oral 0.167 g Granule Oral 20 mg Granule Oral 40 mg Injection, powder, for solution; injection, powder, lyophilized, for solution 40 mg Capsule, delayed release Oral 20 mg/1 Capsule, delayed release Oral 40 mg/1 Granule Oral 11.1 MG Granule, delayed release Oral 10 mg/1 Granule, delayed release Oral 10 mg / sachet Granule, delayed release Oral 2.5 mg/1 Granule, delayed release Oral 20 mg/1 Granule, delayed release Oral 40 mg/1 Granule, delayed release Oral 5 mg/1 Tablet, film coated Oral 40 mg Granule, delayed release Oral 10 MG Tablet Oral 20 mg/1 Tablet Oral 20 MG Injection Intravenous 20 mg/5mL Solution Parenteral 40.000 mg Tablet, film coated Oral Tablet, coated Oral Capsule Oral 44.500 mg Capsule, extended release Oral 40 mg Kit Oral 20 mg/1 Capsule, delayed release Oral 20 mg Capsule, delayed release Oral 40 mg Injection, powder, lyophilized, for solution Intravenous 42.5 mg Tablet, coated Oral 44.55 mg Capsule, coated Oral Tablet Oral 44.569 mg Tablet, delayed release Oral 22545 Mg Solution Intravenous 42.60 mg Injection, powder, for solution Intravenous 40.00 mg Capsule Oral 20.0000 mg Solution Intravenous 42.547 mg Tablet Oral Tablet, delayed release Oral Tablet, extended release Oral Solution 40.000 mg Injection, powder, for solution 40 mg/1vial - Prices
Unit description Cost Unit Nexium i.v. 20 mg vial 33.91USD vial Nexium i.v. 40 mg vial 33.91USD vial NexIUM 20 mg Delayed Release Capsule 6.76USD capsule NexIUM 40 mg Delayed Release Capsule 6.76USD capsule Nexium 10 mg packet 6.5USD each Nexium 20 mg capsule 6.5USD capsule Nexium 20 mg packet 6.5USD each Nexium 40 mg capsule 6.5USD capsule Nexium 40 mg packet 6.5USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5877192 No 1999-03-02 2014-05-27 US CA1338377 No 1996-06-11 2013-06-11 Canada CA2346988 No 2009-02-10 2019-11-03 Canada US6191148 Yes 2001-02-20 2019-04-09 US US6147103 Yes 2000-11-14 2019-04-09 US US6166213 Yes 2000-12-26 2019-04-09 US US5900424 Yes 1999-05-04 2016-11-04 US US6369085 Yes 2002-04-09 2018-11-25 US US6428810 Yes 2002-08-06 2020-05-03 US US7411070 Yes 2008-08-12 2018-11-25 US US8466175 Yes 2013-06-18 2018-11-25 US US8852636 No 2014-10-07 2022-05-31 US US8858996 No 2014-10-14 2022-05-31 US US6926907 No 2005-08-09 2023-02-28 US US7745466 No 2010-06-29 2018-10-13 US US9161920 No 2015-10-20 2022-05-31 US US9198888 No 2015-12-01 2022-05-31 US US8945621 No 2015-02-03 2031-10-17 US US8557285 No 2013-10-15 2022-05-31 US US9220698 No 2015-12-29 2031-03-10 US US5714504 Yes 1998-02-03 2015-08-03 US US9345695 No 2016-05-24 2022-05-31 US US9393208 No 2016-07-19 2029-09-03 US US9707181 No 2017-07-18 2022-05-31 US US10076494 No 2018-09-18 2036-12-08 US US10835488 No 2020-11-17 2036-12-08 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 155 °C Not Available water solubility Very slightly soluble in water Not Available logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.353 mg/mL ALOGPS logP 1.66 ALOGPS logP 2.43 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 9.68 Chemaxon pKa (Strongest Basic) 4.77 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 77.1 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 93.66 m3·mol-1 Chemaxon Polarizability 35.81 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9968 Blood Brain Barrier - 0.6326 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5573 P-glycoprotein inhibitor I Inhibitor 0.6622 P-glycoprotein inhibitor II Non-inhibitor 0.968 Renal organic cation transporter Non-inhibitor 0.542 CYP450 2C9 substrate Non-substrate 0.7838 CYP450 2D6 substrate Substrate 0.6175 CYP450 3A4 substrate Substrate 0.6901 CYP450 1A2 substrate Inhibitor 0.7505 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7895 Ames test Non AMES toxic 0.5692 Carcinogenicity Non-carcinogens 0.8318 Biodegradation Not ready biodegradable 0.9778 Rat acute toxicity 2.2254 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.719 hERG inhibition (predictor II) Non-inhibitor 0.8977
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0udj-0902000000-d7c360235f936b712320 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6t-0049000000-dd6465ff98d6ab7b732e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-1904000000-2c0b41fb687c7276742c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6t-0935000000-8e10633e2e9d56c4305a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0900000000-9fd0b7267901f29c8a26 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-4900000000-c49d95c2f14e14dc5350 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0910000000-3cb2734362e389c7f316 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 204.5956042 predictedDarkChem Lite v0.1.0 [M-H]- 204.4013042 predictedDarkChem Lite v0.1.0 [M-H]- 203.6952042 predictedDarkChem Lite v0.1.0 [M-H]- 181.43503 predictedDeepCCS 1.0 (2019) [M+H]+ 206.3136042 predictedDarkChem Lite v0.1.0 [M+H]+ 205.6878042 predictedDarkChem Lite v0.1.0 [M+H]+ 205.1514042 predictedDarkChem Lite v0.1.0 [M+H]+ 183.79305 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.3173042 predictedDarkChem Lite v0.1.0 [M+Na]+ 204.4892042 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.0212042 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.64558 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- The catalytic subunit of the gastric H(+)/K(+) ATPase pump which transports H(+) ions in exchange for K(+) ions across the apical membrane of parietal cells. Uses ATP as an energy source to pump H(+) ions to the gastric lumen while transporting K(+) ion from the lumen into the cell (By similarity). Remarkably generates a million-fold proton gradient across the gastric parietal cell membrane, acidifying the gastric juice down to pH 1 (By similarity). Within a transport cycle, the transfer of a H(+) ion across the membrane is coupled to ATP hydrolysis and is associated with a transient phosphorylation that shifts the pump conformation from inward-facing (E1) to outward-facing state (E2). The release of the H(+) ion in the stomach lumen is followed by binding of K(+) ion converting the pump conformation back to the E1 state (By similarity).
- Specific Function
- ATP binding
- Gene Name
- ATP4A
- Uniprot ID
- P20648
- Uniprot Name
- Potassium-transporting ATPase alpha chain 1
- Molecular Weight
- 114117.74 Da
References
- Saccar CL: The pharmacology of esomeprazole and its role in gastric acid related diseases. Expert Opin Drug Metab Toxicol. 2009 Sep;5(9):1113-24. doi: 10.1517/17425250903124363. [Article]
- McKeage K, Blick SK, Croxtall JD, Lyseng-Williamson KA, Keating GM: Esomeprazole: a review of its use in the management of gastric acid-related diseases in adults. Drugs. 2008;68(11):1571-607. [Article]
- Vachhani R, Olds G, Velanovich V: Esomeprazole: a proton pump inhibitor. Expert Rev Gastroenterol Hepatol. 2009 Feb;3(1):15-27. doi: 10.1586/17474124.3.1.15. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- The beta subunit of the gastric H(+)/K(+) ATPase pump which transports H(+) ions in exchange for K(+) ions across the apical membrane of parietal cells. Plays a structural and regulatory role in the assembly and membrane targeting of a functionally active pump (By similarity). Within a transport cycle, the transfer of a H(+) ion across the membrane is coupled to ATP hydrolysis and is associated with a transient phosphorylation of the alpha subunit that shifts the pump conformation from inward-facing (E1) to outward-facing state (E2). Interacts with the phosphorylation domain of the alpha subunit and functions as a ratchet, stabilizing the lumenal-open E2 conformation and preventing the reverse reaction of the transport cycle (By similarity).
- Specific Function
- ATPase activator activity
- Gene Name
- ATP4B
- Uniprot ID
- P51164
- Uniprot Name
- Potassium-transporting ATPase subunit beta
- Molecular Weight
- 33366.95 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
- Specific Function
- amino acid binding
- Gene Name
- DDAH1
- Uniprot ID
- O94760
- Uniprot Name
- N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
- Molecular Weight
- 31121.5 Da
References
- Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [Article]
- Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. [Article]
- Modak AS, Klyarytska I, Kriviy V, Tsapyak T, Rabotyagova Y: The effect of proton pump inhibitors on the CYP2C19 enzyme activity evaluated by the pantoprazole-(13)C breath test in GERD patients: clinical relevance for personalized medicine. J Breath Res. 2016 Dec 17;10(4):046017. doi: 10.1088/1752-7163/10/4/046017. [Article]
- Esomeprazole Therapy and CYP2C19 Genotype [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [Article]
- Wedemeyer RS, Blume H: Pharmacokinetic drug interaction profiles of proton pump inhibitors: an update. Drug Saf. 2014 Apr;37(4):201-11. doi: 10.1007/s40264-014-0144-0. [Article]
- 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
- Chioukh R, Noel-Hudson MS, Ribes S, Fournier N, Becquemont L, Verstuyft C: Proton pump inhibitors inhibit methotrexate transport by renal basolateral organic anion transporter hOAT3. Drug Metab Dispos. 2014 Dec;42(12):2041-8. doi: 10.1124/dmd.114.058529. Epub 2014 Sep 19. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 27, 2024 07:15