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
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)
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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.druglib.com/activeingredient/acetohexamide/
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096972 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22260657 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | DYMELOR Approved UseUnknown Launch Date1964 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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60 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12458186/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
289 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12458186/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12458186/ |
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
Dose | Population | Adverse 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 Sources: Diarrhea |
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 |
Other AEs: Hypoglycemia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [Activation >10 uM] | ||||
no [Activation >10 uM] | ||||
no [Activation >10 uM] | ||||
no [Activation >10 uM] | ||||
no [Activation >10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://go.drugbank.com/drugs/DB00414 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Prolonged coma after acetohexamide ingestion. | 1967 Jul 10 |
|
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor. | 1995 Nov 17 |
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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 |
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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 |
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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 |
Substance Class |
Chemical
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LIVERTOX |
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QA10BB31
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C97936
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WHO-ATC |
A10BB31
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6793
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CHEMBL1589
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SUB05223MIG
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DTXSID7020007
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ACETOHEXAMIDE
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m1331
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Acetohexamide
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1134
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DB00414
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759128
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100000087938
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D000092
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C47380
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968-81-0
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213-530-4
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28052
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BINDER->LIGAND |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug I non-uraemic human plasma 1.0-2.2
METABOLITE TO PARENT DRUG RATIO
PLASMA
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METABOLITE ACTIVE -> PARENT |
URINE
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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