Acetohexamide

Last updated
Acetohexamide
Acetohexamide.svg
Acetohexamide ball-and-stick.png
Clinical data
Trade names Dymelor
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a602021
ATC code
Pharmacokinetic data
Protein binding 90%
Identifiers
  • 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 InfoCard 100.012.301 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H20N2O4S
Molar mass 324.40 g·mol−1
3D model (JSmol)
Melting point 188 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) Yes check.svgY
  • Key:VGZSUPCWNCWDAN-UHFFFAOYSA-N Yes check.svgY
   (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. [1]

Contents

Mechanism of action

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

Risks

Sulfonylureas, especially first-generation sulfonylureas such as Acetohexamide, can cause severe hypoglycemia and increase the risk of adverse cardiovascular events. [3] [4]

References

  1. ↑ Montgomery DA (October 1964). "Current Therapeutics. CCII. Acetohexamide". The Practitioner. 193: 555–60. PMID   14216839.
  2. ↑ "Acetohexamide". DrugBank.
  3. ↑ "www.accessdata.fda.gov" (PDF). Archived from the original (PDF) on January 2, 2015.
  4. ↑ "Acetohexamide". Medline Plus. Archived from the original on 11 September 2005.


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