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Acetohexamide

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withacetazolamide.
Pharmaceutical compound
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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.012.301Edit this at Wikidata
Chemical and physical data
FormulaC15H20N2O4S
Molar mass324.40 g·mol−1
3D model (JSmol)
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)

Acetohexamide (trade nameDymelor) is a first-generationsulfonylureamedication used to treatdiabetes mellitus type 2, particularly in people whose diabetes cannot be controlled by diet alone.[1]

Mechanism of action

[edit]

Acetohexamide binds to anATP-sensitive K+ (KATP) channel on the cell membrane ofpancreatic beta cells. This inhibits the outflux ofpotassium, which causes themembrane potential to become more positive. This depolarization in turn opensvoltage-gated calcium channels. The rise in intracellularcalcium leads to increased fusion ofinsulin granulae with the cell membrane, and therefore increased secretion of insulin.[2]

Risks

[edit]

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

References

[edit]
  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).
  4. ^"Acetohexamide".Medline Plus. Archived fromthe original on 11 September 2005.


Oraldiabetes medication,insulins andinsulin analogues, and other drugs used in diabetes (A10)
fast-acting
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inhalable
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Insulin sensitizers
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Combinations
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
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KCaTooltip Calcium-activated potassium channel
Blockers
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K2PsTooltip Tandem pore domain potassium channel
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CFTRTooltip Cystic fibrosis transmembrane conductance regulator
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TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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