- Metrifonate
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Metrifonate 
Systematic (IUPAC) name (RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate Clinical data AHFS/Drugs.com International Drug Names Pregnancy cat. ? Legal status ? Identifiers CAS number 52-68-6 ATC code P02BB01 QP52AB01 QP53AF02 PubChem CID 5853 UNII DBF2DG4G2K 
KEGG C07971 Chemical data Formula C4H8Cl3O4P Mol. mass 257.436 g/mol SMILES eMolecules & PubChem 
(what is this?) (verify)Metrifonate (INN) or trichlorfon (USAN) is an irreversible organophosphate acetylcholinesterase inhibitor.[1] it is a prodrug which is activated non-enzymatically into 2,2-dichlorovinyl dimethyl phosphate (DDVP).
It can be used to treat schistosomiasis caused by Schistoma haematobium but is no longer commercially available.[2]
It has been proposed for use in treatment of Alzheimer's disease, but use for that purpose is not currently recommended.[3]
References
- ^ "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease". http://www.library.nhs.uk/neurological/ViewResource.aspx?resID=237789.
- ^ Ross A.G.P., Bartley P.B., Sleigh A.C., Olds G.R., Li Y., Williams G.M., and McManus D.P. (2002). "Schistosomiasis". The New England Journal of Medicine 346 (16): 1212–1220. doi:10.1056/NEJMra012396. PMID 11961151. http://content.nejm.org/cgi/reprint/346/16/1212.
- ^ 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.
Antiparasitics – Anthelmintics (P02) Antiplatyhelmintic agents Antitrematodals
(schistosomicides)Binds tubulinphosphonic acid (Metrifonate)Other/unknownquinoline (Praziquantel#, Oxamniquine#) • phenol (Bithionol) • thiazole (Niridazole) • arylsulfonate (Stibophen)Anticestodals
(taeniacides)Binds tubulinOther/unknownsalicylanilide (Niclosamide)# • aminoacridine (Quinacrine) • butyrophenone (Desaspidin) • chlorophenol (Dichlorophen)Antinematodal agents
(including
macrofilaricides)Binds tubulinbenzimidazole (Mebendazole#, Albendazole#, Thiabendazole, Fenbendazole, Ciclobendazole, Flubendazole)Other/unknownpiperazine (Piperazine • Diethylcarbamazine#) • thiazole (Levamisole#) • quinolinium (Pyrvinium) • benzylammonium (Bephenium) • naphthalenesulfonate (Suramin#) • Tribendimidine#WHO-EM. ‡Withdrawn from market. Clinical trials: †Phase III. §Never to phase III M: IFT
helm,arth (acar)
helm, arth (lice), zoon
helm, arth
Psychoanaleptics: Antidementia agents (N06D) Anticholinesterases Cymserine • Donepezil • Galantamine • Huperzine A (Huperzia serrata) • Ladostigil • Rivastigmine • TacrineOthers Bifemelane • Bilobalide (Ginkgo biloba) • Cerlapirdine • Ensaculin • Latrepirdine • Lecozotan • Leteprinim • Memantine • SemagacestatCholinergics Receptor ligands Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium bromide • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • PD-0298029 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium bromide • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • Anatoxin-a • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • XenonReuptake inhibitors PlasmalemmalCHT InhibitorsHemicholinium-3 (Hemicholine; HC3) • TriethylcholineVAChT InhibitorsEnzyme inhibitors ChAT inhibitors1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • CatabolismAChE inhibitorsReversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)BChE inhibitorsCymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.Others Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • PirisudanolOthersAcetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • PralidoximeCategories:- Acetylcholinesterase inhibitors
- Phosphonate esters
- Organochlorides
- Antiparasitic agents
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Look at other dictionaries:
Metrifonate — Strukturformel (1S) Trichlorfon (links) bzw. (1R) Trichlorfon (rechts) Allgemeines Name Trichlorfon Andere Namen O,O Dimethyl 2,2,2 trichlor 1 … Deutsch Wikipedia
metrifonate — /mi trif euh nayt /, n. Pharm. an organophosphorus compound, C4H8Cl3O4P, used as an insecticide and anthelmintic. Also called trichlorfon. [appar. contr. of the chemical name] * * * … Universalium
metrifonate — SYN: trichlorfon. * * * met·ri·fo·nate (met″rĭ foґnāt) [USP] an organophosphorus insecticide having potent anticholinesterase activity; especially effective against Schistosoma haematobium. Administered topically or sometimes… … Medical dictionary
metrifonate — /mi trif euh nayt /, n. Pharm. an organophosphorus compound, C4H8Cl3O4P, used as an insecticide and anthelmintic. Also called trichlorfon. [appar. contr. of the chemical name] … Useful english dictionary
Schistosomiasis — Classification and external resources Skin vesicles on the forearm, created by the penetration of Schistosoma. Source: CDC ICD 10 B … Wikipedia
Acetylcholinesterase inhibitor — Acetylcholine … Wikipedia
Dichlorvos — Systematic (IUPAC) name 2,2 … Wikipedia
trichlorfon — An organophosphorus compound effective against immature and mature stages of Schistosoma haematobium, but ineffective against other species of Schistosoma in humans. SYN: metrifonate. * * * tri·chlor·fon also tri·chlor·phon ( )trī klō(ə)r .fän,… … Medical dictionary
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