NAV

Coumaphos

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
3D
Similar Structures
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
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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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcebutololCoumaphos may increase the bradycardic activities of Acebutolol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Coumaphos.
AcetylcholineThe risk or severity of adverse effects can be increased when Coumaphos is combined with Acetylcholine.
AclidiniumCoumaphos may increase the neuromuscular blocking activities of Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Coumaphos.
Food Interactions
Not Available

Products

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International/Other Brands
Meldane

Categories

Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. Janes MJ, Hayes BW, Beardsley DW: Horn fly control with coumaphos. J Econ Entomol. 1968 Oct;61(5):1176-8. [Article]
  5. FAULKNER LC, CARROLL EJ, BENJAMIN M: EFFECT OF COUMAPHOS ON BULLS. J Am Vet Med Assoc. 1964 Sep 1;145:456-9. [Article]
  6. Enzo O: Acute poisoning from food contaminated by coumaphos. Wilderness Environ Med. 2006 Spring;17(1):67-9. [Article]
  7. Authors unspecified: Bioassay of coumaphos for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1979;96:1-203. [Article]
  8. Strickland RK, Gerrish RR: Efficacy of coumaphos against Psoroptes ovis. J Am Vet Med Assoc. 1966 Mar 1;148(5):553-5. [Article]
  9. 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]
  10. 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]
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
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.00148 mg/mLALOGPS
logP4.5ALOGPS
logP4.15Chemaxon
logS-5.4ALOGPS
pKa (Strongest Basic)-7.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area53.99 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity89.93 m3·mol-1Chemaxon
Polarizability34.61 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-06vj-7954000000-80e126f971975f223e60
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0009000000-1eb96120bb8c3511912e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bw9-0039000000-13c6f9257fbc11ac5878
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0091000000-5f535054f0f4f1d40167
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-c875939d86ddad0a8e08
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0590000000-878fbf88eb9b1468b002
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0009000000-de911fe1bfd2b19bcc5f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2209000000-cace1c6ffd146f2e1ca4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-ad1a6b9feda84c4236aa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3609000000-ac9f655144efd5e7cdd9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0944000000-b53b0f7eb8e6597e90cd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-5890000000-4a1e9e06aaf51e0e8e0c
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.9469193
predicted
DarkChem Lite v0.1.0
[M-H]-169.75116
predicted
DeepCCS 1.0 (2019)
[M+H]+185.9815193
predicted
DarkChem Lite v0.1.0
[M+H]+172.10915
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.2458193
predicted
DarkChem Lite v0.1.0
[M+Na]+178.2488
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:21 / Updated at June 12, 2020 16:53