Coumaphos

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

Identification

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Name
Coumaphos
Accession Number
DB11390
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
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
International/Other Brands
Meldane
Categories
UNII
L08SZ5Z5JC
CAS number
56-72-4
Weight
Average: 362.766
Monoisotopic: 362.014458531
Chemical Formula
C14H16ClO5PS
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbexinostatThe risk or severity of QTc prolongation can be increased when Coumaphos is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Coumaphos is combined with Acebutolol.
AceprometazineThe risk or severity of QTc prolongation can be increased when Coumaphos is combined with Aceprometazine.
AcetylcholineThe risk or severity of adverse effects can be increased when Coumaphos is combined with Acetylcholine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Coumaphos is combined with Acetyldigoxin.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Coumaphos.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Coumaphos.
AdenosineThe risk or severity of QTc prolongation can be increased when Coumaphos is combined with Adenosine.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Coumaphos.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Coumaphos.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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. [PubMed:8523496]
  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. [PubMed:10808995]
  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. [PubMed:11990357]
  4. Janes MJ, Hayes BW, Beardsley DW: Horn fly control with coumaphos. J Econ Entomol. 1968 Oct;61(5):1176-8. [PubMed:5680751]
  5. FAULKNER LC, CARROLL EJ, BENJAMIN M: EFFECT OF COUMAPHOS ON BULLS. J Am Vet Med Assoc. 1964 Sep 1;145:456-9. [PubMed:14215377]
  6. Enzo O: Acute poisoning from food contaminated by coumaphos. Wilderness Environ Med. 2006 Spring;17(1):67-9. [PubMed:16538949]
  7. Authors unspecified: Bioassay of coumaphos for possible carcinogenicity. Natl Cancer Inst Carcinog Tech Rep Ser. 1979;96:1-203. [PubMed:12806395]
  8. Strickland RK, Gerrish RR: Efficacy of coumaphos against Psoroptes ovis. J Am Vet Med Assoc. 1966 Mar 1;148(5):553-5. [PubMed:5950512]
  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. [PubMed:46730]
  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. [PubMed:5749116]
External Links
KEGG Drug
D07750
KEGG Compound
C11025
ChemSpider
2768
BindingDB
50366033
ChEBI
3903
ChEMBL
CHEMBL251680
Wikipedia
Coumaphos

Clinical Trials

Clinical Trials
Not Available

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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Coumarin / Aryl thiophosphate / Benzopyran / 1-benzopyran / Thiophosphate triester / Pyranone / Aryl chloride / Aryl halide / Thiophosphoric acid ester / Benzenoid
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)

Drug created on February 25, 2016 11:21 / Updated on June 04, 2019 07:20