Trichlorfon: Difference between revisions

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List of terms related to Trichlorfon

Metrifonate
Clinical data
Synonyms	Trichlorphon
AHFS/Drugs.com	International Drug Names
ATC code	P02BB01 (WHO) Template:ATCvet Template:ATCvet;
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 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C4H8Cl3O4P
Molar mass	257.436 g/mol
3D model (JSmol)	Interactive image;
	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;
(verify)

VisualWikitext

Latest revision as of 17:20, 20 August 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

Template:Anthelmintics

[urlNLH_-_Neurological_Conditions_-_Metrifonate_for_Alzheimers_disease-1] "NLH - Neurological Conditions - Metrifonate for Alzheimer's disease".

[urlschistosomiasis-2] 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.

[3] 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.

[1]

[2]

[3]

@@ Line 1: / Line 1: @@
-{{Chembox new
+{{Drugbox
-|ImageFile=Trichlorfon.PNG
+| verifiedrevid = 447764575
-|ImageSize=
+| IUPAC_name = (''RS'')-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
-|IUPACName=2,2,2-trichloro-1- dimethoxyphosphoryl-ethanol
+| image = Trichlorfon.PNG
-|OtherNames=
+| width = 200
-|Section1= {{Chembox Identifiers
+| imagename = 1 : 1 mixture (racemate)
-|  CASNo=52-68-6
+| drug_name = Metrifonate
-|  PubChem=5853
-|  SMILES=COP(=O)(C(C(Cl)(Cl)Cl)O)OC
+<!--Clinical data-->
-|  MeSHName=Trichlorfon
+| tradename =
-  }}
+| Drugs.com = {{drugs.com|international|metrifonate}}
-|Section2= {{Chembox Properties
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-|  Formula=C<sub>4</sub>H<sub>8</sub>Cl<sub>3</sub>O<sub>4</sub>P
+| pregnancy_US = <!-- A / B            / C / D / X -->
-|  MolarMass=257.436
+| pregnancy_category =
-|  Appearance=
+| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
-|  Density=
+| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
-|  MeltingPt=
+| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
-|  BoilingPt=
+| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
-|  Solubility=
+| legal_status =
-  }}
+| routes_of_administration =
-|Section3= {{Chembox Hazards
-|  MainHazards=
+<!--Pharmacokinetic data-->
-|  FlashPt=
+| bioavailability =
-|  Autoignition=
+| protein_bound =
-  }}
+| metabolism =
+| elimination_half-life =  3 hours
+| excretion =
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 52-68-6
+| CAS_supplemental =
+| ATC_prefix = P02
+| ATC_suffix = BB01
+| ATC_supplemental =  {{ATCvet|P52|AB01}} {{ATCvet|P53|AF02}}
+| PubChem = 5853
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank =
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = DBF2DG4G2K
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = C07971
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 6908
+| synonyms = Trichlorphon
+| ChemSpiderID      = 5644
+<!--Chemical data-->
+| chemical_formula =
+| C=4 | H=8 | Cl=3 | O=4 | P=1
+| molecular_weight = 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
+| InChIKey          = NFACJZMKEDPNKN-UHFFFAOYAJ
+| StdInChI          = 1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
+| StdInChIKey       = NFACJZMKEDPNKN-UHFFFAOYSA-N
 }}
+__NOTOC__
+{{SI}}
 {{CMG}}
-__NOTOC__
+==Overview==
+'''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 |format= |work= |accessdate=}}</ref> It is a prodrug which is activated non-enzymatically into [[2,2-dichlorovinyl dimethyl phosphate]] ([[DDVP]]).
+It is used as an insecticide.
-==Overview==
+It can be used to treat [[schistosomiasis]] caused by ''Schistoma haematobium'' but is no longer commercially available.<ref name="urlschistosomiasis">{{cite journal |doi=10.1056/NEJMra012396 |url=http://content.nejm.org/cgi/reprint/346/16/1212 |title=Schistosomiasis  |journal=The New England Journal of Medicine |author=Ross A.G.P., Bartley P.B., Sleigh A.C., Olds G.R., Li Y., Williams G.M., and McManus D.P.|volume=346 |issue=16 |pages=1212–1220 |year=2002 |pmid=11961151}}</ref>
-'''Trichlorfon''' is an [[organophosphate]] [[acetylcholinesterase inhibitor]].
+It has been proposed for use in treatment of [[Alzheimer's disease]], but use for that purpose is not currently recommended.<ref>{{cite journal |author=López-Arrieta J, Schneider L |editor1-last=López-Arrieta |editor1-first=Jess |title=Metrifonate for Alzheimer's disease |journal=Cochrane Database of Systematic Reviews |volume= |issue=1 |pages=CD003155 |year=2008 |doi=10.1002/14651858.CD003155.pub3 |pmid=16625573}}</ref>
+== References ==
+{{Reflist|2}}
 {{Anthelmintics}}
+[[Category:Insecticides]]
+[[Category:Antiparasitic agents]]
 [[Category:Organophosphate insecticides]]
+[[Category:Anticholinesterases]]
-[[de:Trichlorfon]]
+[[Category:Organochlorides]]
-[[ru:Хлорофос]]
+[[Category:Drug]]
-{{WikiDoc Help Menu}}
-{{WikiDoc Sources}}

Trichlorfon: Difference between revisions

Latest revision as of 17:20, 20 August 2015

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