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Acetohexamide

Summary

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]

Acetohexamide
Clinical data
Trade namesDymelor
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa602021
ATC code
Pharmacokinetic data
Protein binding90%
Identifiers
  • 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
CompTox Dashboard (EPA)
  • DTXSID7020007 Edit this at Wikidata
ECHA InfoCard100.012.301 Edit this at Wikidata
Chemical and physical data
FormulaC15H20N2O4S
Molar mass324.40 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point188 to 190 °C (370 to 374 °F)
  • O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(C(=O)C)cc2
  • 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)

Mechanism of action edit

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 edit

Oral hypoglycemic drugs, including acetohexamide, have been associated with increased cardiovascular mortality. Qualified healthcare professionals should consulted for possible risks, benefits, and alternatives of using this drug for treatment of type 2 diabetes.[3]

References edit

  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.