Metrifonate

Metrifonate

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; O,O-Dimetil-(2,2,2-tricloro-1-idrossi-etil)-fosfonato; Phosphonic acid, (1-hydroxy-2,2,2-trichloroethyl)-, dimethyl ester; Proxol; Trichloorfon; Trichlorofon; Trichlorophon; Trinex; 1-Hydroxy-2,2,2-trichloro-ethyle phosphonate de dimethyle; 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]
AHFS/Drugs.com	International Drug Names
ATC code	P02BB01 (WHO) QP52AB01 (WHO) QP53AF02 (WHO)
Pharmacokinetic data
Biological half-life	3 hours
Identifiers
IUPAC name (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
Synonyms	Trichlorphon
CAS Number	52-68-6
PubChem (CID)	5853
ChemSpider	5644
UNII	DBF2DG4G2K
KEGG	C07971
ChEBI	CHEBI:6908
ECHA InfoCard	100.000.137
Chemical and physical data
Formula	C4H8Cl3O4P
Molar mass	257.436 g/mol
3D model (Jmol)	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 2,2-dichlorovinyl dimethyl phosphate (DDVP).

It is used as an insecticide.

It can be used to treat schistosomiasis^[4] caused by Schistoma haematobium,^[5] but is no longer commercially available.^[6]

It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended.^[7]

References

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.
3. "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease".
4. "Monographs: Pharmaceutical substances: Metrifonate (Metrifonatum)". The International Pharmacopoeia Fourth Edition. WHO. Retrieved 2015-10-20.
5. "Helminths: Schistosomiasis: Metrifonate". WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition. WHO. 1995. Retrieved 2015-10-20.
6. Ross A.G.P.; Bartley P.B.; Sleigh A.C.; Olds G.R.; Li Y.; Williams G.M.; McManus D.P. (2002). "Schistosomiasis". The New England Journal of Medicine. 346 (16): 1212–1220. doi:10.1056/NEJMra012396. PMID 11961151.
7. López-Arrieta J, Schneider L (2008). López-Arrieta, Jess, ed. "Metrifonate for Alzheimer's disease". Cochrane Database of Systematic Reviews (1): CD003155. doi:10.1002/14651858.CD003155.pub3. PMID 16625573.