NAV

Metrifonate

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

Identification

Generic Name
Metrifonate
DrugBank Accession Number
DB11473
Background

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

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 257.437
Monoisotopic: 255.922578377
Chemical Formula
C4H8Cl3O4P
Synonyms
  • (±)-Trichlorfon
  • 1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester
  • Chlorophos
  • Methyl chlorophos
  • Metrifonate
  • Métrifonate
  • Metrifonato
  • Metrifonatum
  • Trichlorfon

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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.
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AcebutololMetrifonate may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Metrifonate is combined with Acetylcholine.
AclidiniumMetrifonate may increase the neuromuscular blocking activities of Aclidinium.
AmantadineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Metrifonate.
AmifampridineThe risk or severity of adverse effects can be increased when Metrifonate is combined with Amifampridine.
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.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Metrifonate.
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Food Interactions
Not Available

Categories

ATC Codes
P02BB01 — Metrifonate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Chlorohydrin / Dialkyl alkylphosphonate / Halohydrin / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organochloride
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organochlorine compound, organic phosphonate, phosphonic ester (CHEBI:6908) / Organophosphorus insecticides (C07971)
Affected organisms
Not Available

Chemical Identifiers

UNII
DBF2DG4G2K
CAS number
52-68-6
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

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. [Article]
  2. Martinez F, Jarillo JA, Orus MI: Interactions between trichlorfon and three Chlorophyceae. Bull Environ Contam Toxicol. 1991 Apr;46(4):599-605. [Article]
  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. [Article]
  4. Orus MI, Marco E: Disappearance of trichlorfon from cultures with different cyanobacteria. Bull Environ Contam Toxicol. 1991 Sep;47(3):392-7. [Article]
  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. [Article]
  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. [Article]
  7. Authors unspecified: Trichlorfon. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jan;30:207-31. [Article]
  8. Dobson KJ: Trichlorfon toxicity in pigs. Aust Vet J. 1977 Mar;53(3):115-7. [Article]
  9. Hagan CJ: More on febantel and trichlorfon. Vet Med Small Anim Clin. 1979 Jan;74(1):6. [Article]
  10. Csik V, Motika D, Marosi GY: Delayed neuropathy after trichlorfon intoxication. J Neurol Neurosurg Psychiatry. 1986 Feb;49(2):222. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D00805
KEGG Compound
C07971
ChemSpider
5644
BindingDB
50286920
RxNav
1000581
ChEBI
6908
ChEMBL
CHEMBL167150
Wikipedia
Metrifonate

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 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

Drug created at February 25, 2016 19:03 / Updated at June 12, 2020 16:53