View source for Acetohexamide

{{Short description|Chemical compound}}
{{distinguish|acetazolamide}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 477239096
| IUPAC_name = 1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea      

  4-acetyl-''N''-(cyclohexylcarbamoyl)benzenesulfonamide
| image = Acetohexamide.svg
| image2 = Acetohexamide_ball-and-stick.png
<!--Clinical data-->
| tradename = Dymelor
| Drugs.com = {{drugs.com|CONS|acetohexamide}}
| MedlinePlus = a602021
| pregnancy_category =  
| legal_status =  
| routes_of_administration =  
<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound = 90%
| metabolism =  
| elimination_half-life =  
<!--Identifiers-->
| IUPHAR_ligand = 6793
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 968-81-0
| ATC_prefix = A10
| ATC_suffix = BB31
| ATC_supplemental =  
| PubChem = 1989
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00414
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1912
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QGC8W08I6I
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00219
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28052
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1589
<!--Chemical data-->
| C=15 | H=20
| N=2 | O=4
| S=1
| smiles = O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(C(=O)C)cc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VGZSUPCWNCWDAN-UHFFFAOYSA-N
| melting_point = 188
| melting_high = 190
}}

'''Acetohexamide''' (trade name '''Dymelor''') is a first-generation [[sulfonylurea]] [[medication]] used to treat [[diabetes mellitus type 2]], 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>

==Mechanism of action==

Acetohexamide binds to an [[ATP-sensitive potassium channel|ATP-sensitive K<sup>+</sup>]] (K<sub>ATP</sub>) channel on the cell membrane of [[pancreatic beta cell]]s. This inhibits the outflux of [[potassium in biology|potassium]], which causes the [[membrane potential]] to become more positive. This depolarization in turn opens [[voltage-gated calcium channel]]s. The rise in intracellular [[calcium in biology|calcium]] leads to increased fusion of [[Granule_(cell_biology)#Insulin_granules_in_beta_cells|insulin granulae]] 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>

==Risks==
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 |archive-url=https://web.archive.org/web/20150102172806/http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/017532s030lbl.pdf |url-status=dead |archive-date=January 2, 2015 |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>

==References==
{{Reflist}}


{{Oral hypoglycemics}}
{{Ion channel modulators}}

[[Category:Potassium channel blockers]]
[[Category:1-(Benzenesulfonyl)-3-cyclohexylureas]]
[[Category:Aromatic ketones]]

{{Gastrointestinal-drug-stub}}