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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 (max)
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)
n = 100
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 61.6 (26-87)
Sex: M+F
Population Size: 100
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
n = 1
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 74
Sex: M
Population Size: 1
Sources:
Other AEs: Hypoglycemia...
Other AEs:
Hypoglycemia
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea Disc. AE
2 g 1 times / day multiple, oral (max)
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)
n = 100
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 61.6 (26-87)
Sex: M+F
Population Size: 100
Sources:
Diffuse pain Disc. AE
2 g 1 times / day multiple, oral (max)
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)
n = 100
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 61.6 (26-87)
Sex: M+F
Population Size: 100
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
n = 1
Health Status: unhealthy
Condition: diabetes mellitus
Age Group: 74
Sex: M
Population Size: 1
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
The structure and function of the ATP-sensitive K+ channel in insulin-secreting pancreatic beta-cells.
1999 Apr
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
Strain- and sex-related differences of carbonyl reductase activities in kidney microsomes and cytosol of rats.
2004 Nov-Dec
[Studies for analyzing the prohibited ingredients such as acetohexamide in cosmetics].
2005
Rosiglitazone and myocardial infarction in patients previously prescribed metformin.
2009 Jun 27
Pancreatic beta-cell signaling: toward better understanding of diabetes and its treatment.
2010
A new method of urethroplasty for prevention of fistula in female-to-male gender reassignment surgery.
2010 Jun
Characterization of the binding of sulfonylurea drugs to HSA by high-performance affinity chromatography.
2010 Jun 1

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 Fri Dec 15 15:09:04 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:04 GMT 2023
Record UNII
QGC8W08I6I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETOHEXAMIDE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
33006
Code 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 Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
WHO-VATC QA10BB31
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
NCI_THESAURUS C97936
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
WHO-ATC A10BB31
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
Code System Code Type Description
HSDB
3280
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
RXCUI
173
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY RxNorm
IUPHAR
6793
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
ChEMBL
CHEMBL1589
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
EVMPD
SUB05223MIG
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID7020007
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
WIKIPEDIA
ACETOHEXAMIDE
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
FDA UNII
QGC8W08I6I
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
PUBCHEM
1989
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
MERCK INDEX
m1331
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY Merck Index
LACTMED
Acetohexamide
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
INN
1134
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
DRUG BANK
DB00414
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
NSC
759128
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
SMS_ID
100000087938
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
MESH
D000092
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
NCI_THESAURUS
C47380
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
CAS
968-81-0
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
DRUG CENTRAL
57
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-530-4
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
CHEBI
28052
Created by admin on Fri Dec 15 15:09:04 GMT 2023 , Edited by admin on Fri Dec 15 15:09:04 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Metabolite to parent drug I non-uraemic human plasma 1.0-2.2
METABOLITE TO PARENT DRUG RATIO
PLASMA
METABOLITE ACTIVE -> PARENT
URINE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC