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

Category:Aromatic ketones

{{Gastrointestinal-drug-stub}}