Acetohexamide

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.[1]

Not to be confused with acetazolamide.
Acetohexamide
Clinical data
Trade namesDymelor
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa602021
ATC code
Pharmacokinetic data
Protein binding90%
Identifiers
IUPAC name
  • 1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea 4-acetyl-N-(cyclohexylcarbamoyl)benzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.301
Chemical and physical data
FormulaC15H20N2O4S
Molar mass324.40 g·mol−1
3D model (JSmol)
Melting point188 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
  (verify)

Mechanism of action

Acetohexamide bind to an ATP-sensitive K+ (KATP) 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.[2]

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.[3]

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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