| Revision as of 19:52, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457487337 of page Acetohexamide for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 21:25, 12 July 2024 edit Rcfische2 (talk | contribs)106 edits Actually, this sounds better. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{distinguish|acetazolamide}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457457565 |
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| verifiedrevid = 477239096 |
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| IUPAC_name = 4-acetyl-''N''-(cyclohexylcarbamoyl)benzenesulfonamide |
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| IUPAC_name = 1--3-cyclohexylurea |
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| image = Acetohexamide.svg |
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4-acetyl-''N''-(cyclohexylcarbamoyl)benzenesulfonamide |
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| image = Acetohexamide.svg |
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| image2 = Acetohexamide_ball-and-stick.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Dymelor |
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| tradename = Dymelor |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 6793 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 968-81-0 |
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| CAS_number = 968-81-0 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = 1989 |
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| PubChem = 1989 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00414 |
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| DrugBank = DB00414 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1589 |
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| ChEMBL = 1589 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=15 | H=20 | N=2 | O=4 | S=1 |
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| C=15 | H=20 |
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| N=2 | O=4 |
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| S=1 |
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| molecular_weight = 324.395 g/mol |
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| smiles = O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(C(=O)C)cc2 |
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| smiles = O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(C(=O)C)cc2 |
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| InChI = 1/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19) |
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| InChIKey = VGZSUPCWNCWDAN-UHFFFAOYAN |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19) |
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| StdInChI = 1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VGZSUPCWNCWDAN-UHFFFAOYSA-N |
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| StdInChIKey = VGZSUPCWNCWDAN-UHFFFAOYSA-N |
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| melting_point = 188 |
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| melting_high = 190 |
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}} |
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}} |
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'''Acetohexamide''' (trade name '''Dymelor''') is a first-generation ] ] used to treat ], particularly in people whose diabetes cannot be controlled by diet alone.<ref name="pmid14216839">{{cite journal | vauthors = Montgomery DA | title = Current Therapeutics. CCII. Acetohexamide | journal = The Practitioner | volume = 193 | issue = | pages = 555–60 | date = October 1964 | pmid = 14216839 | doi = | url = }}</ref> |
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==Mechanism of action== |
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Acetohexamide binds to an ] (K<sub>ATP</sub>) channel on the cell membrane of ]s. This inhibits the outflux of ], which causes the ] to become more positive. This depolarization in turn opens ]s. The rise in intracellular ] leads to increased fusion of ] with the cell membrane, and therefore increased secretion of insulin.<ref>{{cite web | title = Acetohexamide | url = https://go.drugbank.com/drugs/DB00414 | work = DrugBank }}</ref> |
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==Risks== |
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Sulfonylureas, especially first-generation sulfonylureas such as Acetohexamide, can cause severe hypoglycemia and increase the risk of adverse cardiovascular events. <ref>{{cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/017532s030lbl.pdf |title=www.accessdata.fda.gov}}</ref><ref>{{cite web | title = Acetohexamide | url = https://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a682478.html | work = Medline Plus | archive-url = https://web.archive.org/web/20050911024428/http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a682478.html | archive-date = 11 September 2005 }}</ref> |
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==References== |
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{{Reflist}} |
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{{Oral hypoglycemics}} |
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{{Ion channel modulators}} |
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] |
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] |
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] |
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{{Gastrointestinal-drug-stub}} |