Metrifonate

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
Metrifonate
Accession Number
DB11473
Type
Small Molecule
Groups
Vet approved
Description

Metrifonate or trichlorfon is an irreversible organophosphate acetylcholinesterase inhibitor. It is a prodrug which is activated non-enzymatically into 2,2-dichlorovinyl dimethyl phosphate.

Structure
Thumb
Synonyms
  • (±)-Trichlorfon
  • 1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester
  • Chlorophos
  • Methyl chlorophos
  • Metrifonate
  • Métrifonate
  • Metrifonato
  • Metrifonatum
  • Trichlorfon
Categories
UNII
DBF2DG4G2K
CAS number
52-68-6
Weight
Average: 257.437
Monoisotopic: 255.922578377
Chemical Formula
C4H8Cl3O4P
InChI Key
NFACJZMKEDPNKN-UHFFFAOYSA-N
InChI
InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
IUPAC Name
dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
SMILES
COP(=O)(OC)C(O)C(Cl)(Cl)Cl

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Metrifonate.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Metrifonate.
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Metrifonate.
AmikacinThe therapeutic efficacy of Metrifonate can be decreased when used in combination with Amikacin.
AmitriptylineThe therapeutic efficacy of Amitriptyline can be decreased when used in combination with Metrifonate.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Metrifonate.
AmoxapineThe therapeutic efficacy of Amoxapine can be decreased when used in combination with Metrifonate.
Anisotropine methylbromideThe therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Metrifonate.
ApramycinThe therapeutic efficacy of Metrifonate can be decreased when used in combination with Apramycin.
AprobarbitalThe therapeutic efficacy of Aprobarbital can be decreased when used in combination with Metrifonate.
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
    Evidence Level

    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. Czeizel AE, Elek C, Gundy S, Metneki J, Nemes E, Reis A, Sperling K, Timar L, Tusnady G, Viragh Z: Environmental trichlorfon and cluster of congenital abnormalities. Lancet. 1993 Feb 27;341(8844):539-42. [PubMed:8094783]
  2. Martinez F, Jarillo JA, Orus MI: Interactions between trichlorfon and three Chlorophyceae. Bull Environ Contam Toxicol. 1991 Apr;46(4):599-605. [PubMed:1855006]
  3. Wu ML, Deng JF: Acute hemolysis caused by incidental trichlorfon exposure. J Chin Med Assoc. 2009 Apr;72(4):214-8. doi: 10.1016/S1726-4901(09)70058-9. [PubMed:19372080]
  4. Orus MI, Marco E: Disappearance of trichlorfon from cultures with different cyanobacteria. Bull Environ Contam Toxicol. 1991 Sep;47(3):392-7. [PubMed:1768954]
  5. Xu WN, Liu WB, Liu ZP: Trichlorfon-induced apoptosis in hepatocyte primary cultures of Carassius auratus gibelio. Chemosphere. 2009 Nov;77(7):895-901. doi: 10.1016/j.chemosphere.2009.08.043. Epub 2009 Sep 22. [PubMed:19775726]
  6. Wang X, Tang Q, Wang Q, Qiao X, Xu Z: Study of a molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography for simultaneous determination of trace trichlorfon and monocrotophos residues in vegetables. J Sci Food Agric. 2014 May;94(7):1409-15. doi: 10.1002/jsfa.6429. Epub 2013 Oct 31. [PubMed:24122545]
  7. Authors unspecified: Trichlorfon. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jan;30:207-31. [PubMed:6578181]
  8. Dobson KJ: Trichlorfon toxicity in pigs. Aust Vet J. 1977 Mar;53(3):115-7. [PubMed:869797]
  9. Hagan CJ: More on febantel and trichlorfon. Vet Med Small Anim Clin. 1979 Jan;74(1):6. [PubMed:256352]
  10. Csik V, Motika D, Marosi GY: Delayed neuropathy after trichlorfon intoxication. J Neurol Neurosurg Psychiatry. 1986 Feb;49(2):222. [PubMed:3950648]
  11. Okuyama A, Arima T, Goto Y, Imai M, Haraoka S: [A case of hypocholinesterasemia induced by trichlorfon]. Acta Med Okayama. 1975 Jun;29(3):233-6. [PubMed:127517]
  12. Brocard P, Pfister K: [Efficacy of the oral antiparasitic mebendazole plus trichlorfon (telmin plus trichlorfon) against Gasterophilus in the horse]. Schweiz Arch Tierheilkd. 1993;135(11-12):356-9. [PubMed:8266053]
External Links
KEGG Drug
D00805
KEGG Compound
C07971
ChemSpider
5644
BindingDB
50286920
ChEBI
6908
ChEMBL
CHEMBL167150
Wikipedia
Metrifonate
ATC Codes
P02BB01 — Metrifonate

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 Solubility7.17 mg/mLALOGPS
logP0.81ALOGPS
logP1.14ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.59 m3·mol-1ChemAxon
Polarizability19.33 Å3ChemAxon
Number of Rings0ChemAxon
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
GC-MS Spectrum - EI-BGC-MSsplash10-0bvi-6900000000-bc340a4a5dc69af91e1c
Mass Spectrum (Electron Ionization)MSsplash10-0bvj-8900000000-7ca1c4413fd81f66277d
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Phosphonic acid diesters
Direct Parent
Dialkyl alkylphosphonates
Alternative Parents
Phosphonic acid esters / Chlorohydrins / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Dialkyl alkylphosphonate / Phosphonic acid ester / Halohydrin / Chlorohydrin / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organophosphorus compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organochlorine compound, organic phosphonate, phosphonic ester (CHEBI:6908) / Organophosphorus insecticides (C07971)

Drug created on February 25, 2016 12:03 / Updated on December 14, 2018 05:46