| Revision as of 14:58, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit |
Latest revision as of 19:50, 7 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Chloroarenes; added Category:2-Chlorophenyl compounds using HotCat |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 401596207 |
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| verifiedrevid = 456686940 |
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| IUPAC_name = 2,2'-''bis'' |
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| IUPAC_name = 2,2'-''bis'' |
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| image = Ambenonium.svg |
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| image = Ambenonium.svg |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 7648-98-8 |
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| CAS_number = 7648-98-8 |
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| ATC_prefix = N07 |
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| ATC_prefix = N07 |
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| ATC_suffix = AA30 |
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| ATC_suffix = AA30 |
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| PubChem = 8288 |
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| PubChem = 8288 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = <!-- blanked - oldvalue: APRD00771 --> |
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| DrugBank = DB01122 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7987 |
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| ChemSpiderID = 7987 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01001 |
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| KEGG = D01001 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 2628 |
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| ChEBI = 2628 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1652 --> |
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| ChEMBL = 1652 |
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<!--Chemical data--> |
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| C=28 | H=42 | Cl=2 | N=4 | O=2 | charge = +2 |
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| C=28 | H=42 | Cl=2 | N=4 | O=2 | charge = +2 |
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| molecular_weight = 537.564 g/mol |
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| smiles = ..Clc1ccccc1C(CC)(CC)CCNC(=O)C(=O)NCC(Cc2ccccc2Cl)(CC)CC |
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| smiles = ..Clc1ccccc1C(CC)(CC)CCNC(=O)C(=O)NCC(Cc2ccccc2Cl)(CC)CC |
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| InChI = 1/C28H40Cl2N4O2.2ClH/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30;;/h9-16H,5-8,17-22H2,1-4H3;2*1H |
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| InChIKey = DXUUXWKFVDVHIK-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C28H40Cl2N4O2.2ClH/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30;;/h9-16H,5-8,17-22H2,1-4H3;2*1H |
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| StdInChI = 1S/C28H40Cl2N4O2.2ClH/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30;;/h9-16H,5-8,17-22H2,1-4H3;2*1H |
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| StdInChIKey = DXUUXWKFVDVHIK-UHFFFAOYSA-N |
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| StdInChIKey = DXUUXWKFVDVHIK-UHFFFAOYSA-N |
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}} |
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}} |
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'''Ambenonium''' (as '''ambenonium dichloride''', trade name '''Mytelase''') is a ]<ref name="pmid13679187">{{cite journal |author=Bolognesi ML, Cavalli A, Andrisano V, ''et al.'' |title=Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors |journal=Farmaco |volume=58 |issue=9 |pages=917–28 |year=2003 |month=September |pmid=13679187 |doi= 10.1016/S0014-827X(03)00150-2|url=http://linkinghub.elsevier.com/retrieve/pii/S0014827X03001502}}</ref> used in the management of ]. |
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'''Ambenonium''' (as '''ambenonium dichloride''', trade name '''Mytelase''') is a ]<ref name="pmid13679187">{{cite journal |vauthors =Bolognesi ML, Cavalli A, Andrisano V |title=Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors |journal=Farmaco |volume=58 |issue=9 |pages=917–28 |date=September 2003 |pmid=13679187 |doi= 10.1016/S0014-827X(03)00150-2|display-authors=etal}}</ref> used in the management of ]. |
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It is classified as reversible.<ref name="pmid1588924">{{cite journal |author=Hodge AS, Humphrey DR, Rosenberry TL |title=Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities |journal=Mol. Pharmacol. |volume=41 |issue=5 |pages=937–42 |year=1992 |month=May |pmid=1588924 |doi= |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1588924}}</ref> |
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It is classified as a reversible cholinesterase inhibitor.<ref name="pmid1588924">{{cite journal |vauthors =Hodge AS, Humphrey DR, Rosenberry TL |title=Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities |journal=Mol. Pharmacol. |volume=41 |issue=5 |pages=937–42 |date=May 1992 |pmid=1588924 |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1588924}}</ref> |
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==Mechanism of Action== |
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'''Ambenonium''' exerts its actions against ] by competitive reversible inhibition of ], the enzyme responsible for the hydrolysis of acetylcholine. Myasthenia Gravis occurs when the body produces antibodies against acetylcholine receptors, and thus inhibits signal transmission across the myoneural junction. Ambenonium reversibly binds acetylcholinesterase, inactivates it and therefore increases levels of acetylcholine. This, in turn, facilitates transmission of impulses across the myoneural junction and effectively treats the disease |
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==Mechanism of action== |
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Ambenonium exerts its actions against ] by competitive reversible inhibition of ], the enzyme responsible for the hydrolysis of acetylcholine. Myasthenia gravis occurs when the body produces antibodies against acetylcholine receptors, and thus inhibits signal transmission across the neuromuscular junction. Ambenonium reversibly binds acetylcholinesterase, inactivates it and therefore increases levels of acetylcholine. This, in turn, facilitates transmission of impulses across the myoneural junction and effectively treats the disease. |
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==Indications== |
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==Indications== |
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Ambenonium is used to treat muscle weakness due to muscle disease (myasthenia gravis). |
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Ambenonium is used to treat muscle weakness due to disease or defect of the neuromuscular junction (]). |
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Ambenonium was withdrawn from the market in the United States in 2010.<ref>{{Cite web | url = http://www.stelizabeth.com/ADAM/doc/Thomson%20DrugNotes/45/5103.htm | publisher = St. Elizabeth Healthcare | title = Ambenonium | access-date = 2016-02-10 | archive-url = https://web.archive.org/web/20150908065032/http://www.stelizabeth.com/ADAM/doc/Thomson%20DrugNotes/45/5103.htm | archive-date = 2015-09-08 | url-status = dead }}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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{{Acetylcholine metabolism and transport modulators}} |
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{{Cholinergics}} |
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{{nervous-system-drug-stub}} |
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{{nervous-system-drug-stub}} |
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] |
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