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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.druglib.com/activeingredient/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. 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

Sources: Farmakologiya i Toksikologiya (Moscow) (1959), 22, 512-16.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DYMELOR

Approved Use

Unknown

Launch Date

1964
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60 μg/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYHEXAMIDE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
289 μg × h/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYHEXAMIDE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
HYDROXYHEXAMIDE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 61.6 (26-87)
Health Status: unhealthy
Age Group: 61.6 (26-87)
Sex: M+F
Sources:
Disc. AE: Diffuse pain, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diffuse pain
Diarrhea
Sources:
0.5 g 1 times / day multiple, oral
Recommended
Dose: 0.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 g, 1 times / day
Sources:
unhealthy, 74
Health Status: unhealthy
Age Group: 74
Sex: M
Sources:
Other AEs: Hypoglycemia...
Other AEs:
Hypoglycemia
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea Disc. AE
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 61.6 (26-87)
Health Status: unhealthy
Age Group: 61.6 (26-87)
Sex: M+F
Sources:
Diffuse pain Disc. AE
2 g 1 times / day multiple, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: multiple
Dose: 2 g, 1 times / day
Sources:
unhealthy, 61.6 (26-87)
Health Status: unhealthy
Age Group: 61.6 (26-87)
Sex: M+F
Sources:
Hypoglycemia
0.5 g 1 times / day multiple, oral
Recommended
Dose: 0.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 g, 1 times / day
Sources:
unhealthy, 74
Health Status: unhealthy
Age Group: 74
Sex: M
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [Activation >10 uM]
no [Activation >10 uM]
no [Activation >10 uM]
no [Activation >10 uM]
no [Activation >10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Prolonged coma after acetohexamide ingestion.
1967 Jul 10
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor.
1995 Nov 17
Hypoglycemic effect of S(-)-hydroxyhexamide, a major metabolite of acetohexamide, and its enantiomer R(+)-hydroxyhexamide.
2001 Sep 7
Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats.
2002 Dec
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus].
2003
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Barriers to self-monitoring of blood glucose among adults with diabetes in an HMO: a cross sectional study.
2003 Mar 19
Analysis of synthetic anti-diabetic drugs in adulterated traditional Chinese medicines by high-performance capillary electrophoresis.
2003 Sep 19
Strain- and sex-related differences of carbonyl reductase activities in kidney microsomes and cytosol of rats.
2004 Nov-Dec
Metformin, sulfonylureas, or other antidiabetes drugs and the risk of lactic acidosis or hypoglycemia: a nested case-control analysis.
2008 Nov
Chromatographic studies of changes in binding of sulfonylurea drugs to human serum albumin due to glycation and fatty acids.
2010 Nov 15
Use of peak decay analysis and affinity microcolumns containing silica monoliths for rapid determination of drug-protein dissociation rates.
2011 Apr 15
Epac2: a sulfonylurea receptor?
2012 Feb

Sample Use Guides

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
Created
by admin
on Mon Mar 31 17:48:11 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:11 GMT 2025
Record UNII
QGC8W08I6I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
33006
Preferred Name English
ACETOHEXAMIDE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
acetohexamide [INN]
Common Name English
ACETOHEXAMIDE [HSDB]
Common Name English
ACETOHEXAMIDE [MI]
Common Name English
BENZENESULFONAMIDE, 4-ACETYL-N-((CYCLOHEXYLAMINO)CARBONYL)
Common Name English
ACETOHEXAMIDE [VANDF]
Common Name English
DYMELOR
Common Name English
ACETOHEXAMIDE [JAN]
Common Name English
ACETOHEXAMIDE [USP IMPURITY]
Common Name English
1-((P-ACETYLPHENYL)SULFONYL)-3-CYCLOHEXYLUREA
Common Name English
Acetohexamide [WHO-DD]
Common Name English
ACETOHEXAMIDE [MART.]
Common Name English
ACETOHEXAMIDE [USAN]
Common Name English
ACETOHEXAMIDE [ORANGE BOOK]
Common Name English
NSC-759128
Code English
Classification Tree Code System Code
LIVERTOX 10
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
WHO-VATC QA10BB31
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
NCI_THESAURUS C97936
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
WHO-ATC A10BB31
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
Code System Code Type Description
HSDB
3280
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
RXCUI
173
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY RxNorm
IUPHAR
6793
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL1589
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
EVMPD
SUB05223MIG
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID7020007
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
WIKIPEDIA
ACETOHEXAMIDE
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
FDA UNII
QGC8W08I6I
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
PUBCHEM
1989
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
MERCK INDEX
m1331
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY Merck Index
LACTMED
Acetohexamide
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
INN
1134
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
DRUG BANK
DB00414
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
NSC
759128
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
SMS_ID
100000087938
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
MESH
D000092
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
NCI_THESAURUS
C47380
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
CAS
968-81-0
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
DRUG CENTRAL
57
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-530-4
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
CHEBI
28052
Created by admin on Mon Mar 31 17:48:11 GMT 2025 , Edited by admin on Mon Mar 31 17:48:11 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
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METABOLITE TO PARENT DRUG RATIO
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METABOLITE ACTIVE -> PARENT
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Name Property Type Amount Referenced Substance Defining Parameters References
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