Metrifonate information

Metrifonate
Clinical data
Trade names	Chlorophos (and many others) Trichlorfon; Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl) dimethylphosphonate; Agroforotox; Anthon; Chlorofos; Chloroftalm; Chlorophos; Chlorophthalm; Chloroxyphos; Combot; Dimethyl (trichlorohydroxyethyl)phosphonate; Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate; Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate; Dipterax; Dipterex; Dipterex 50; Diptevur; Ditrifon; Dylox; Dyrex; Dyvon; DEP; DEP (Pesticide); DETF; ENT 19,763; Flibol E; Fliegenteller; Forotox; Foschlor; Foschlor R; Foschlor R 50; Hypodermacid; Loisol; Masoten; Mazoten; Methyl Chlorophos; Metifonate; Metriphonate; Neguron; Neguvon; O,O-Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate; O,O-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate; O,O-Dimethyl (2,2,2-trichlorohydroxyethyl)phosphonate; Phoschlor; Phoschlor R50; Polfoschlor; Ricifon; Ritsifon; Soldep; Sotipox; Trichlorphon; Trichlorphon FN; Tugon; Volfartol; Votexit; Wotexit; WEC 50; (1-Hydroxy-2,2,2-trichloroethyl)phosphonic acid, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl)phosphonate, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester; Bayer L 1359; Bilarcil; Bovinox; Briton; BAY 15922; Cekufon; Chlorophosciclosom; Clorofos; Danex; Dimethoxy-(2,2,2-trichloro-1-hydroxyethyl)phosphine oxide; Equino-Aid; Foschlorem; Khloroftalm; NCI-C54831; O,O-Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphate; O,O-Dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphosaeure ester; O,O-Dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat; O,O-Dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat; O,O-Dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat; Phosphonic acid, (1-hydroxy-2,2,2-trichloroethyl)-, dimethyl ester; Proxol; Trichloorfon; Trichlorofon; Trichlorophon; Trinex; Bay-L 1359; Briten; Denkaphon; Dipterex WP 80; Ertefon; OMS 800; Zeltivar; Onefon; O,O-Dimethyl-1-oxy-2,2,2-trichloroethyl phosphonate;Trichlorfon; 1-Hydroxy-2,2,2-trichloroethylphosphonate-O,O-dimethyl ester; Phosphonic acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester; Chlorak; Dimetox; Dioxaphos
Other names	Trichlorphon
AHFS/Drugs.com	International Drug Names
ATC code	P02BB01 (WHO) QP52AB01 (WHO) QP53AF02 (WHO);
Pharmacokinetic data
Elimination half-life	3 hours
Identifiers
	IUPAC name (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate;
CAS Number	52-68-6 ;
PubChem CID	5853;
ChemSpider	5644 ;
UNII	DBF2DG4G2K;
KEGG	C07971 ;
ChEBI	CHEBI:6908 ;
CompTox Dashboard (EPA)	DTXSID0021389 ;
ECHA InfoCard	100.000.137
Chemical and physical data
Formula	C4H8Cl3O4P
Molar mass	257.43 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES COP(=O)(C(C(Cl)(Cl)Cl)O)OC;
	InChI InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 ; Key:NFACJZMKEDPNKN-UHFFFAOYSA-N ;
	(what is this?) (verify)

Metrifonate (INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor.^[3] It is a prodrug which is activated non-enzymatically into the active agent dichlorvos.

It is used as an insecticide. According to the US Environmental Protection Agency trichlorfon has been used on golf course turf, home lawns, non-food contact areas of food and meat processing plants, ornamental shrubs and plants, and ornamental and baitfish ponds. Used to control caterpillars, white grubs, mole crickets, cattle lice, sod webworms, leaf miners, stink bugs, flies, ants, cockroaches, earwigs, crickets, diving beetle, water scavenger beetle, water boatman backswimmer, water scorpions, giant water bugs and pillbugs.^[4] After reregistration, a number of its uses were voluntarily restricted, and currently, it is used in nonfood areas to control flies, roaches, and ants among other pests. Outdoors it is used on ornamental plants, golf courses, and lawn grass to treat lepidopteran larvae pests, it is also used to treat flies in animal husbandry in areas that are not accessible to animals, it also used to control harvester ants.^[5]

It can be used to treat schistosomiasis^[6] caused by Schistosoma haematobium,^[7] but is no longer commercially available.^[8]

It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended.^[9]

^ "Trichlorfon". Haz-Map. U.S. National Library of Medicine. August 2015. Retrieved 2015-10-13.
^ "Metrifonate". U.S. National Institute of Standards and Technology. Retrieved 2016-09-04.
^ "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease". Archived from the original on 2009-07-19.
^ "Trichlorfon Facts". Pesticides: Reregistration. U.S. Environmental Protection Agency.
^ "Trichlorfon". R.E.D. Facts. U.S. Environmental Protection Agency.
^ "Monographs: Pharmaceutical substances: Metrifonate (Metrifonatum)". The International Pharmacopoeia Fourth Edition. WHO. Archived from the original on June 3, 2016. Retrieved 2015-10-20. (dead link 31 January 2019)
^ "Helminths: Schistosomiasis: Metrifonate". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition. WHO. 1995. Archived from the original on July 15, 2010. Retrieved 2015-10-20.
^ Ross AG, Bartley PB, Sleigh AC, Olds GR, Li Y, Williams GM, McManus DP (April 2002). "Schistosomiasis" (PDF). The New England Journal of Medicine. 346 (16): 1212–20. doi:10.1056/NEJMra012396. PMID 11961151.
^ López-Arrieta JM, Schneider L (April 2006). López-Arrieta J (ed.). "Metrifonate for Alzheimer's disease". The Cochrane Database of Systematic Reviews (2): CD003155. doi:10.1002/14651858.CD003155.pub3. PMID 16625573.

[1] "Trichlorfon". Haz-Map. U.S. National Library of Medicine. August 2015. Retrieved 2015-10-13.

[2] "Metrifonate". U.S. National Institute of Standards and Technology. Retrieved 2016-09-04.

[urlNLH_-_Neurological_Conditions_-_Metrifonate_for_Alzheimers_disease-3] "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease". Archived from the original on 2009-07-19.

[4] "Trichlorfon Facts". Pesticides: Reregistration. U.S. Environmental Protection Agency.

[5] "Trichlorfon". R.E.D. Facts. U.S. Environmental Protection Agency.

[6] "Monographs: Pharmaceutical substances: Metrifonate (Metrifonatum)". The International Pharmacopoeia Fourth Edition. WHO. Archived from the original on June 3, 2016. Retrieved 2015-10-20. (dead link 31 January 2019)

[7] "Helminths: Schistosomiasis: Metrifonate". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition. WHO. 1995. Archived from the original on July 15, 2010. Retrieved 2015-10-20.

[urlschistosomiasis-8] Ross AG, Bartley PB, Sleigh AC, Olds GR, Li Y, Williams GM, McManus DP (April 2002). "Schistosomiasis" (PDF). The New England Journal of Medicine. 346 (16): 1212–20. doi:10.1056/NEJMra012396. PMID 11961151.

[9] López-Arrieta JM, Schneider L (April 2006). López-Arrieta J (ed.). "Metrifonate for Alzheimer's disease". The Cochrane Database of Systematic Reviews (2): CD003155. doi:10.1002/14651858.CD003155.pub3. PMID 16625573.

Metrifonate information

and 27 Related for: Metrifonate information

Metrifonate

Acetylcholinesterase inhibitor

Praziquantel

Tetrahydrocannabinol

List of drugs used to treat schistosomiasis

Caffeine

Schistosomiasis

Anticholinergic

Nerve agent

Sarin

Carbendazim

Botulinum toxin

Gasterophilus intestinalis

Dichlorvos

Pyridostigmine

ATC code P02

Donepezil

Ethylcholine mustard

Neostigmine

Parathion

Novichok

Dicyclohexyl phosphorofluoridate

Itopride

Acetylcholine

Fenobucarb

Diazinon

Carbofuran

Clinical data

Trade names	Chlorophos (and many others)^[1] Trichlorfon; Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl) dimethylphosphonate; Agroforotox; Anthon; Chlorofos; Chloroftalm; Chlorophos; Chlorophthalm; Chloroxyphos; Combot; Dimethyl (trichlorohydroxyethyl)phosphonate; Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate; Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate; Dipterax; Dipterex; Dipterex 50; Diptevur; Ditrifon; Dylox; Dyrex; Dyvon; DEP; DEP (Pesticide); DETF; ENT 19,763; Flibol E; Fliegenteller; Forotox; Foschlor; Foschlor R; Foschlor R 50; Hypodermacid; Loisol; Masoten; Mazoten; Methyl Chlorophos; Metifonate; Metriphonate; Neguron; Neguvon; O,O-Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate; O,O-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate; O,O-Dimethyl (2,2,2-trichlorohydroxyethyl)phosphonate; Phoschlor; Phoschlor R50; Polfoschlor; Ricifon; Ritsifon; Soldep; Sotipox; Trichlorphon; Trichlorphon FN; Tugon; Volfartol; Votexit; Wotexit; WEC 50; (1-Hydroxy-2,2,2-trichloroethyl)phosphonic acid, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl)phosphonate, dimethyl ester; (2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester; Bayer L 1359; Bilarcil; Bovinox; Briton; BAY 15922; Cekufon; Chlorophosciclosom; Clorofos; Danex; Dimethoxy-(2,2,2-trichloro-1-hydroxyethyl)phosphine oxide; Equino-Aid; Foschlorem; Khloroftalm; NCI-C54831; O,O-Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphate; O,O-Dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphosaeure ester; O,O-Dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat; O,O-Dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat; O,O-Dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat; Phosphonic acid, (1-hydroxy-2,2,2-trichloroethyl)-, dimethyl ester; Proxol; Trichloorfon; Trichlorofon; Trichlorophon; Trinex; Bay-L 1359; Briten; Denkaphon; Dipterex WP 80; Ertefon; OMS 800; Zeltivar; Onefon; O,O-Dimethyl-1-oxy-2,2,2-trichloroethyl phosphonate;Trichlorfon; 1-Hydroxy-2,2,2-trichloroethylphosphonate-O,O-dimethyl ester; Phosphonic acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester; Chlorak; Dimetox; Dioxaphos^[2]
Other names	Trichlorphon
AHFS/Drugs.com	International Drug Names
ATC code	P02BB01 (WHO) QP52AB01 (WHO) QP53AF02 (WHO)
Pharmacokinetic data
Elimination half-life	3 hours
Identifiers
IUPAC name (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
CAS Number	52-68-6^Y
PubChem CID	5853
ChemSpider	5644^N
UNII	DBF2DG4G2K
KEGG	C07971^Y
ChEBI	CHEBI:6908^N
CompTox Dashboard (EPA)	DTXSID0021389
ECHA InfoCard	100.000.137
Chemical and physical data
Formula	C₄H₈Cl₃O₄P
Molar mass	257.43 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES COP(=O)(C(C(Cl)(Cl)Cl)O)OC
InChI InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3^N Key:NFACJZMKEDPNKN-UHFFFAOYSA-N^N
^NY (what is this?) (verify)