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Acetohexamide

Clinical data
Trade names	Dymelor
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a602021
ATC code	A10BB31 (WHO)
Pharmacokinetic data
Protein binding	90%
Identifiers
IUPAC name 1--3-cyclohexylurea 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
CAS Number	968-81-0
PubChem CID	1989
IUPHAR/BPS	6793
DrugBank	DB00414
ChemSpider	1912
UNII	QGC8W08I6I
KEGG	D00219
ChEBI	CHEBI:28052
ChEMBL	ChEMBL1589
CompTox Dashboard (EPA)	DTXSID7020007
ECHA InfoCard	100.012.301
Chemical and physical data
Formula	C15H20N2O4S
Molar mass	324.40 g·mol
3D model (JSmol)	Interactive image
Melting point	188 to 190 °C (370 to 374 °F)
SMILES O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(C(=O)C)cc2
InChI InChI=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) Key:VGZSUPCWNCWDAN-UHFFFAOYSA-N
(verify)

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.

Mechanism of action

Acetohexamide bind to an ATP-sensitive K (K_ATP) channel on the cell membrane of pancreatic beta cells. This inhibits the out flux 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.

Risks

Oral hypoglycemic drugs, including acetohexamide, have been associated with increased cardiovascular mortality.

References

1. Montgomery DA (October 1964). "Current Therapeutics. CCII. Acetohexamide". The Practitioner. 193: 555–60. PMID 14216839.
2. "Acetohexamide". DrugBank.
3. "Acetohexamide". Medline Plus. Archived from the original on 11 September 2005.

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