Metrifonate: Difference between revisions

{{short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid = 447764575

| chirality = [[Racemic mixture]]

| tradename = Chlorophos (and many others)<ref>{{Cite web|url=http://hazmap.nlm.nih.gov/category-details?id=1141&table=copytblagents|title=Trichlorfon|date=August 2015|website=Haz-Map|publisher=U.S. National Library of Medicine|access-date=2015-10-13}}</ref> 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<ref>{{Cite web|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C52686&Mask=4 |title=Metrifonate|publisher=U.S. National Institute of Standards and Technology|access-date=2016-09-04}}</ref>

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| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = 3 hours

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| CAS_number_Ref = {{cascite|correct|??}}

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| DrugBank =

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 6908

| synonyms = Trichlorphon

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5644

| chemical_formula =

| C=4 | H=8 | Cl=3 | O=4 | P=1

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = NFACJZMKEDPNKN-UHFFFAOYSA-N

'''Metrifonate''' ([[International Nonproprietary Name|INN]]) or '''trichlorfon''' ([[United States Adopted Name|USAN]]) is an irreversible [[organophosphate]] [[acetylcholinesterase inhibitor]].<ref name="urlNLH - Neurological Conditions - Metrifonate for Alzheimers disease">{{cite web |url=http://www.library.nhs.uk/neurological/ViewResource.aspx?resID=237789 |title=NLH - Neurological Conditions - Metrifonate for Alzheimer's disease |archive-url=https://web.archive.org/web/20090719215237/http://www.library.nhs.uk/neurological/ViewResource.aspx?resID=237789 |archive-date=2009-07-19 |url-status=dead }}</ref> 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.<ref>{{cite journal | title = Trichlorfon Facts | url = https://archive.epa.gov/pesticides/reregistration/web/html/trichlorfon_fs.html | journal = Pesticides: Reregistration | publisher = U.S. Environmental Protection Agency }}</ref> 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 plant]]s, 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]].<ref>{{cite web | title = Trichlorfon | url = https://nepis.epa.gov/Exe/tiff2png.cgi/P100AFOA.PNG?-r+75+-g+7+D%3A%5CZYFILES%5CINDEX%20DATA%5C95THRU99%5CTIFF%5C00002508%5CP100AFOA.TIF | work = R.E.D. Facts | publisher = U.S. Environmental Protection Agency }}</ref>

It can be used to treat [[schistosomiasis]]<ref>{{Cite web|url=http://apps.who.int/phint/en/d/Jb/6.1.271.html|archive-url=https://web.archive.org/web/20160603181623/http://apps.who.int/phint/en/d/Jb/6.1.271.html|url-status=dead|archive-date=June 3, 2016|title=Monographs: Pharmaceutical substances: Metrifonate (Metrifonatum)|website=The International Pharmacopoeia Fourth Edition|publisher=[[WHO]]|access-date=2015-10-20}} (dead link 31 January 2019)</ref> caused by ''[[Schistosoma haematobium]]'',<ref>{{Cite web|url=http://apps.who.int/medicinedocs/en/d/Jh2922e/3.7.2.html|archive-url=https://web.archive.org/web/20100715114822/http://apps.who.int/medicinedocs/en/d/Jh2922e/3.7.2.html|url-status=dead|archive-date=July 15, 2010|title=Helminths: Schistosomiasis: Metrifonate|date=1995|work=WHO Model Prescribing Information: Drugs Used in Parasitic Diseases - Second Edition|publisher=[[WHO]]|access-date=2015-10-20}}</ref> but is no longer commercially available.<ref name="urlschistosomiasis">{{cite journal | vauthors = Ross AG, Bartley PB, Sleigh AC, Olds GR, Li Y, Williams GM, McManus DP | title = Schistosomiasis | journal = The New England Journal of Medicine | volume = 346 | issue = 16 | pages = 1212–20 | date = April 2002 | pmid = 11961151 | doi = 10.1056/NEJMra012396 | url = https://espace.library.uq.edu.au/view/UQ:64149/UQ64149_OA.pdf }}</ref>

It has been proposed for use in treatment of [[Alzheimer's disease]], but use for that purpose is not currently recommended.<ref>{{cite journal | vauthors = López-Arrieta JM, Schneider L | title = Metrifonate for Alzheimer's disease | journal = The Cochrane Database of Systematic Reviews | issue = 2 | pages = CD003155 | date = April 2006 | pmid = 16625573 | doi = 10.1002/14651858.CD003155.pub3 | editor1-last = López-Arrieta | editor1-first = Jess }}</ref>

==Bans and restrictions==

In the United States, trichlorfon/metrifonate may only be used on nonfood and nonfeed sites.<ref name="epa">{{cite web |url=https://archive.epa.gov/pesticides/reregistration/web/pdf/0104.pdf |title=Reregistration Eligibility Decision Trichlorfon |access-date=2018-08-09 }}</ref>

Trichlorfon/metrifonate was banned in the [[EU]] in 2008 (Regulation (EC) 689/2008) and in Brazil in 2010.<ref name="rotterdam">{{cite web |url=http://www.pic.int/Portals/5/download.aspx?d=UNEP-FAO-RC-DGD-Trichlorfon.En.pdf |title=Decision Guidance Document Trichlorfon - Rotterdam Convention |access-date=2018-08-09 }}</ref>

Trichlorfon/metrifonate was banned in Argentina in 2018,<ref name="argent">{{cite web |url=http://news.agropages.com/News/NewsDetail---26404.htm |title=Argentina bans dichlorvos and trichlorfon |access-date=2018-08-09 }}</ref> noting that trichlorvon converts to [[dichlorvos]] by metabolism in plants, as well as by biodegradation of the soil.

Trichlorfon/metrifonate was banned in New Zealand in 2011.<ref name="nz">{{cite web |url=https://agrow.agribusinessintelligence.informa.com/AG009095/New-Zealand-bans-trichlorfon |title=New Zealand bans trichlorfon |access-date=2018-08-09 }}</ref>

Trichlorfon/metrifonate was banned in India from 2020.<ref name="india">{{cite web |url=http://abcofagri.com/banned-pesticides-in-india/ |title=Banned Pesticides in India |access-date=2018-08-09 |date=2018-01-17 }}</ref>

{{Insecticides}}

{{Acetylcholine metabolism and transport modulators}}

[[Category:Insecticides]]

[[Category:Organophosphate insecticides]]

[[Category:Phosphonate esters]]

[[Category:Trichloromethyl compounds]]

[[Category:Prodrugs]]

{{antiinfective-drug-stub}}