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Details

Stereochemistry ACHIRAL
Molecular Formula C15H20N2O4S
Molecular Weight 324.395
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETOHEXAMIDE

SMILES

CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2CCCCC2

InChI

InChIKey=VGZSUPCWNCWDAN-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H20N2O4S
Molecular Weight 324.395
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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. It lowers blood sugar by stimulating the pancreatic beta cells to secrete insulin and by helping the body use insulin efficiently. The pancreas must produce insulin for this medication to work. Acetohexamide binds to an ATP-dependent K+ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing out flux of potassium, which causes the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granule with the cell membrane, and therefore increased secretion of (pro) insulin. Acetohexamide extensively metabolized in the liver to the active metabolite hydroxyhexamide, which exhibits greater hypoglycemic potency than acetohexamide. Hydroxyhexamide is believed to be responsible for prolonged hypoglycemic effects. Symptoms of an acetohexamide overdose include hunger, nausea, anxiety, cold sweats, weakness, drowsiness, unconsciousness, and coma. Acetohexamide has been discontinued in the US market.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DYMELOR

Cmax

ValueDoseCo-administeredAnalytePopulation
60 μg/mL
10 mg/kg single, intravenous
HYDROXYHEXAMIDE plasma
Rattus norvegicus

AUC

ValueDoseCo-administeredAnalytePopulation
289 μg × h/mL
10 mg/kg single, intravenous
HYDROXYHEXAMIDE plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
10 mg/kg single, intravenous
HYDROXYHEXAMIDE plasma
Rattus norvegicus

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
250 mg once daily; dose can be increased as needed by 250– 500 mg daily every 5– 7 days (not to exceed 1.5 g/day; doses 1 g/day should be given as divided doses).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
QGC8W08I6I
Record Status Validated (UNII)
Record Version