Chemistry:Acetohexamide

Short description: Chemical compound

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-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
CAS Number	968-81-0 Y
PubChem CID	1989
IUPHAR/BPS	6793
DrugBank	DB00414 Y
ChemSpider	1912 Y
UNII	QGC8W08I6I
KEGG	D00219 Y
ChEBI	CHEBI:28052 Y
ChEMBL	ChEMBL1589 Y
Chemical and physical data
Formula	C15H20N2O4S
Molar mass	324.40 g·mol−1
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) Y Key:VGZSUPCWNCWDAN-UHFFFAOYSA-N Y
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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. Talk to your doctor about the possible risks, benefits, and alternatives of using this drug for your condition.