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
| tradename = Dymelor
| Drugs.com = {{drugs.com|CONS|acetohexamide}}
| MedlinePlus = a602021
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound = 90%
| metabolism =
| elimination_half-life =
| 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
| 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.{{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 = }}
Mechanism of action
Acetohexamide binds to an ATP-sensitive K+ (KATP) channel on the cell membrane of pancreatic beta cells. This inhibits the outflux of potassium, which causes the membrane potential to become more positive. This depolarization in turn opens voltage-gated calcium channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of insulin.{{cite web | title = Acetohexamide | url = https://go.drugbank.com/drugs/DB00414 | work = DrugBank }}
Risks
Sulfonylureas, especially first-generation sulfonylureas such as Acetohexamide, can cause severe hypoglycemia and increase the risk of adverse cardiovascular events. {{cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/017532s030lbl.pdf |title=www.accessdata.fda.gov}}{{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 }}
References
{{Reflist}}
{{Oral hypoglycemics}}
{{Ion channel modulators}}
Category:Potassium channel blockers
Category:1-(Benzenesulfonyl)-3-cyclohexylureas
{{Gastrointestinal-drug-stub}}