Coumaphos
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Coumaphos
- DrugBank Accession Number
- DB11390
- Background
This drug is a fat-soluble phosphorothioate agent that kills both insects and mites. It is non-volatile in nature and is well known by a variety of names as such a dip or wash. Coumaphos is widely used for both farm and domestic animals to control ticks, mites, flies and fleas.
- Type
- Small Molecule
- Groups
- Vet approved
- Structure
- Weight
- Average: 362.766
Monoisotopic: 362.014458531 - Chemical Formula
- C14H16ClO5PS
- Synonyms
- 3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate
- 3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester
- 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin
- 3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate
- Coumafos
- Coumaphos
- O-(3-chloro-4-methyl-2-oxo-2H-chromen-7-yl) O,O-diethyl thiophosphate
- O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphate
- O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphorothioate
- Phosphorothioic acid, O-(3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl ester
- External IDs
- BAYER 21199
- BAYER-21199
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- 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 Integrate drug-drug
interactions in your softwareAcebutolol Coumaphos may increase the bradycardic activities of Acebutolol. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Coumaphos. Acetylcholine The risk or severity of adverse effects can be increased when Coumaphos is combined with Acetylcholine. Aclidinium Coumaphos may increase the neuromuscular blocking activities of Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Coumaphos. - Food Interactions
- Not Available
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.
- International/Other Brands
- Meldane
Categories
- Drug Categories
- Agrochemicals
- Anthelmintics
- Anti-Infective Agents
- Antinematodal Agents
- Antiparasitic Agents
- Benzopyrans
- Cholinergic Agents
- Cholinesterase Inhibitors
- Compounds used in a research, industrial, or household setting
- Coumarins
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Insecticides
- Neurotransmitter Agents
- Organophosphates
- Organophosphorus Compounds
- Organothiophosphates
- Organothiophosphorus Compounds
- Pesticides
- Potential QTc-Prolonging Agents
- Pyrans
- QTc Prolonging Agents
- Sulfur Compounds
- Toxic Actions
- Umbelliferones
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Coumarins and derivatives
- Sub Class
- Not Available
- Direct Parent
- Coumarins and derivatives
- Alternative Parents
- Aryl thiophosphates / 1-benzopyrans / Thiophosphate triesters / Pyranones and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds show 3 more
- Substituents
- 1-benzopyran / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Aryl thiophosphate / Benzenoid / Benzopyran / Coumarin / Heteroaromatic compound / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organochlorine compound, organic thiophosphate, organothiophosphate insecticide (CHEBI:3903) / Acaricides (C11025) / a small molecule (CPD-8964)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- L08SZ5Z5JC
- CAS number
- 56-72-4
- InChI Key
- BXNANOICGRISHX-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3
- IUPAC Name
- O-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate
- SMILES
- CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2
References
- General References
- Fang TC, Chen KW, Wu MH, Sung JM, Huang JJ: Coumaphos intoxications mimic food poisoning. J Toxicol Clin Toxicol. 1995;33(6):699-703. [Article]
- Jindal T, Singh DK, Agarwal HC: Persistence, degradation and leaching of coumaphos in soil. J Environ Sci Health B. 2000 May;35(3):309-20. [Article]
- Jindal T, Singh DK, Agarwal HC: Persistence and degradation of coumaphos in model cattle dipping vats. J Environ Sci Health B. 2002 Jan;37(1):33-42. [Article]
- Janes MJ, Hayes BW, Beardsley DW: Horn fly control with coumaphos. J Econ Entomol. 1968 Oct;61(5):1176-8. [Article]
- FAULKNER LC, CARROLL EJ, BENJAMIN M: EFFECT OF COUMAPHOS ON BULLS. J Am Vet Med Assoc. 1964 Sep 1;145:456-9. [Article]
- Enzo O: Acute poisoning from food contaminated by coumaphos. Wilderness Environ Med. 2006 Spring;17(1):67-9. [Article]
- Authors unspecified: Bioassay of coumaphos for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1979;96:1-203. [Article]
- Strickland RK, Gerrish RR: Efficacy of coumaphos against Psoroptes ovis. J Am Vet Med Assoc. 1966 Mar 1;148(5):553-5. [Article]
- Silvestri R, Himes JA, Edds GT: Repeated oral administration of coumaphos in sheep: interactions of coumaphos with bishydroxycoumarin, trichlorfon, and phenobarbital sodium. Am J Vet Res. 1975 Mar;36(3):289-92. [Article]
- Train CT, White RG, Hansen MF: Efficacy of coumaphos and naphthalophos against nematodes of lambs. Am J Vet Res. 1968 Dec;29(12):2331-5. [Article]
- External Links
- KEGG Drug
- D07750
- KEGG Compound
- C11025
- ChemSpider
- 2768
- BindingDB
- 50366033
- ChEBI
- 3903
- ChEMBL
- CHEMBL251680
- ZINC
- ZINC000000608284
- PDBe Ligand
- WZ0
- Wikipedia
- Coumaphos
- PDB Entries
- 8h7r
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00148 mg/mL ALOGPS logP 4.5 ALOGPS logP 4.15 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) -7.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 53.99 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 89.93 m3·mol-1 Chemaxon Polarizability 34.61 Å3 Chemaxon Number of Rings 2 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 184.9469193 predictedDarkChem Lite v0.1.0 [M-H]- 169.75116 predictedDeepCCS 1.0 (2019) [M+H]+ 185.9815193 predictedDarkChem Lite v0.1.0 [M+H]+ 172.10915 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.2458193 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.2488 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:21 / Updated at June 12, 2020 16:53