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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/27 16:50:40」(JST)

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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 is used as an insecticide.

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".
^ 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.
^ 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.

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UpToDate Contents

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1. 住血吸虫症の治療および予防 treatment and prevention of schistosomiasis

English Journal

Cholinesterase activity in the tissues of bivalves Noah's ark shell (Arca noae) and warty venus (Venus verrucosa): characterisation and in vitro sensitivity to organophosphorous pesticide trichlorfon.

Perić L, Ribarić L, Nerlović V.SourceRuđer Bošković Instititute, Center for Marine Research, G. Paliaga 5, 52210 Rovinj, Croatia. lorena.peric@cim.irb.hr
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology.Comp Biochem Physiol B Biochem Mol Biol.2013 Aug;165(4):243-9. doi: 10.1016/j.cbpb.2013.05.002. Epub 2013 May 20.
Cholinesterase (ChE, EC 3.1.1.7) activity was investigated in gills and adductor muscle of two bivalve species: Arca noae and Venus verrucosa. The properties of ChEs were investigated using acetylcholine iodide (ASCh), butyrylcholine iodide (BSCh) and propionylcholine iodide (PrSCh) as substrates an
PMID 23701992

Molecular and immunological responses of the giant freshwater prawn, Macrobrachium rosenbergii, to the organophosphorus insecticide, trichlorfon.

Chang CC, Rahmawaty A, Chang ZW.SourceDepartment of Aquaculture, National Pingtung University of Science and Technology, Taiwan, ROC. changcc@mail.npust.edu.tw
Aquatic toxicology (Amsterdam, Netherlands).Aquat Toxicol.2013 Apr 15;130-131:18-26. doi: 10.1016/j.aquatox.2012.12.024. Epub 2013 Jan 8.
Trichlorfon is an organophosphorus (OP) insecticide that is used as an agriculture pesticide to destroy insects, a human medicine to combat internal parasites, and an ectoparasiticide in the livestock and aquaculture industries, but which has caused aquatic toxicity in the prawn industry. The aim of
PMID 23340335

Simultaneous Determination of Nine Trace Organophosphorous Pesticide Residues in Fruit Samples Using Molecularly Imprinted Matrix Solid-Phase Dispersion Followed by Gas Chromatography.

Wang X, Qiao X, Ma Y, Zhao T, Xu Z.SourceCollege of Food Science and Engineering, Shandong Agricultural University , Tai'an 271018, People's Republic of China.
Journal of agricultural and food chemistry.J Agric Food Chem.2013 Apr 12. [Epub ahead of print]
How to determine trace multipesticide residues in fruits is an important problem. This paper reports a molecularly imprinted polymer (MIP) that was prepared using 4-(dimethoxyphosphorothioylamino)butanoic acid as the template, acrylamide as the functional monomer, and ethylene glycol dimethacrylate
PMID 23544352

Japanese Journal

Comparative brain cholinesterase inhibiting activity of Glycyrrhiza glabra, Myristica fragrans, ascorbic acid and metrifonate in mice

DHINGRA D.
J. Med. Food 9, 281-283, 2006
NAID 30018245720

Efficacy of metrifonate in improving the psychiatric and behavioral disturbances of patients with Alzheimer's disease

CUMMINGS JL
J Geriatr Psychiatr Neurol 14, 101-108, 2001
NAID 30026459725

<Abstract of Published Report>Effects of Metrifonate on Memory Impairment and Cholinergic Dysfunction in Rats.

ITOH Akio,NITTA Atsumi,KATONO Yuki,USUI Miho,NARUHASHI Kazumasa,IIDA Ryuichi,HASEGAWA Takaaki,NABESHIMA Toshitaka
岐阜藥科大學紀要 47, 79, 1998-06-30
NAID 110000054110

Related Pictures

★リンクテーブル★

リンク元	「駆虫薬」「メトリホナート」「trichlorfon」「メトリホネート」

「駆虫薬」

Metrifonate
Systematic (IUPAC) name
	(RS)-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Pharmacokinetic data
Half-life	3 hours
Identifiers
CAS number	52-68-6
ATC code	P02BB01 QP52AB01 QP53AF02
PubChem	CID 5853
ChemSpider	5644
UNII	DBF2DG4G2K
KEGG	C07971
ChEBI	CHEBI:6908
Synonyms	Trichlorphon
Chemical data
Formula	C4H8Cl3O4P
Mol. mass	257.436 g/mol
	SMILES COP(=O)(C(C(Cl)(Cl)Cl)O)OC InChI = 1/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3;
	InChI InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3; Key:NFACJZMKEDPNKN-UHFFFAOYSA-N ;
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英: anthelmintic, anthelmintics
ラ: anthelmintica
関

http://en.wikipedia.org/wiki/Anthelmintic

antiplatyhelmintic agents	Antitrematodals (schistosomicides)	binds tubulin	benzimidazole (Triclabendazole#)
		acetylcholinesterase inhibitor	phosphonic acid (metrifonate)
		Other/unknown	quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen)
	anticestodals (taeniacides)	binds tubulin	benzimidazole (albendazole#)
	anticestodals (taeniacides)	Other/unknown	salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen)
antinematodal agents (macrofilaricides)		binds tubulin	benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole)
		chloride channel	macrolide (ivermectin#)
		NMDA	tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel)
		Other/unknown	piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine