Acetohexamide

Not to be confused with acetazolamide.

Acetohexamide

File:Acetohexamide.svg
File:Acetohexamide ball-and-stick.png
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 checkY
PubChem CID	1989
IUPHAR/BPS	6793
DrugBank	DB00414 checkY
ChemSpider	1912 checkY
UNII	QGC8W08I6I
KEGG	D00219 checkY
ChEBI	CHEBI:28052 checkY
ChEMBL	ChEMBL1589 checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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) checkY Key:VGZSUPCWNCWDAN-UHFFFAOYSA-N checkY
(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 binds to an ATP-sensitive K⁺ (K_ATP) 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.

Risks

Sulfonylureas, especially first-generation sulfonylureas such as Acetohexamide, can cause severe hypoglycemia and increase the risk of adverse cardiovascular events.