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
Structure for Metrifonate (DB11473)
- 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 WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our 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 Metrifonate may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Metrifonate is combined with Acetylcholine. Aclidinium Metrifonate may increase the neuromuscular blocking activities of Aclidinium. Amantadine The therapeutic efficacy of Amantadine can be decreased when used in combination with Metrifonate. Amifampridine The risk or severity of adverse effects can be increased when Metrifonate is combined with Amifampridine. Amitriptyline The therapeutic efficacy of Amitriptyline can be decreased when used in combination with Metrifonate. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Metrifonate. Amoxapine The therapeutic efficacy of Amoxapine can be decreased when used in combination with Metrifonate. Anisotropine methylbromide The therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Metrifonate. Aripiprazole The therapeutic efficacy of Aripiprazole can be decreased when used in combination with Metrifonate. 
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- Not Available
Categories
- ATC Codes
- P02BB01 — Metrifonate
- Drug Categories
- Agrochemicals
- Anthelmintics
- Anti-Infective Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antitrematodals
- Cholinergic Agents
- Cholinesterase Inhibitors
- Compounds used in a research, industrial, or household setting
- Enzyme Inhibitors
- Insecticides
- Neurotransmitter Agents
- Organophosphonates
- Organophosphorous Compounds
- Organophosphorus Compounds
- Pesticides
- Toxic Actions
- 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
- 1MVY4KU98F
- 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
- 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]
- Martinez F, Jarillo JA, Orus MI: Interactions between trichlorfon and three Chlorophyceae. Bull Environ Contam Toxicol. 1991 Apr;46(4):599-605. [Article]
- 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]
- Orus MI, Marco E: Disappearance of trichlorfon from cultures with different cyanobacteria. Bull Environ Contam Toxicol. 1991 Sep;47(3):392-7. [Article]
- 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]
- 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]
- Authors unspecified: Trichlorfon. IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jan;30:207-31. [Article]
- Dobson KJ: Trichlorfon toxicity in pigs. Aust Vet J. 1977 Mar;53(3):115-7. [Article]
- Hagan CJ: More on febantel and trichlorfon. Vet Med Small Anim Clin. 1979 Jan;74(1):6. [Article]
- Csik V, Motika D, Marosi GY: Delayed neuropathy after trichlorfon intoxication. J Neurol Neurosurg Psychiatry. 1986 Feb;49(2):222. [Article]
- 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]
- 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]
- External Links
- KEGG Drug
- D00805
- KEGG Compound
- C07971
- ChemSpider
- 5644
- BindingDB
- 50286920
- 1000581
- ChEBI
- 6908
- ChEMBL
- CHEMBL167150
- Wikipedia
- Metrifonate
Clinical Trials
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 7.17 mg/mL ALOGPS logP 0.81 ALOGPS logP 1.14 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 10.12 ChemAxon pKa (Strongest Basic) -4.9 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 55.76 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 47.59 m3·mol-1 ChemAxon Polarizability 19.33 Å3 ChemAxon Number of Rings 0 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
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-0bvi-6900000000-bc340a4a5dc69af91e1c Mass Spectrum (Electron Ionization) MS splash10-0bvj-8900000000-7ca1c4413fd81f66277d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Drug created on February 25, 2016 19:03 / Updated on June 12, 2020 16:53