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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:59 UTC
HMDB IDHMDB14558
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetohexamide
DescriptionAcetohexamide is only found in individuals that have used or taken this drug. It is a sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide. [PubChem]Sulfonylureas such as acetohexamide bind to an ATP-dependent K+ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing outflux 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 granulae with the cell membrane, and therefore increased secretion of (pro)insulin.
Structure
Thumb
Synonyms
ValueSource
1-((P-Acetylphenyl)sulfonyl)-3-cyclohexylureaChEBI
4-Acetyl-N-((cyclohexylamino)carbonyl)benzenesulfonamideChEBI
AcetohexamidaChEBI
AcetohexamidumChEBI
DymelorChEBI
N-(P-Acetylphenylsulfonyl)-n'-cyclohexylureaChEBI
1-((P-Acetylphenyl)sulphonyl)-3-cyclohexylureaGenerator
4-Acetyl-N-((cyclohexylamino)carbonyl)benzenesulphonamideGenerator
N-(P-Acetylphenylsulphonyl)-n'-cyclohexylureaGenerator
AcetohexamidHMDB
Chemical FormulaC15H20N2O4S
Average Molecular Weight324.395
Monoisotopic Molecular Weight324.114377828
IUPAC Name3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
Traditional Nameacetohexamide
CAS Registry Number968-81-0
SMILES
CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
InChI Identifier
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)
InChI KeyInChIKey=VGZSUPCWNCWDAN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Sulfonylurea
  • Cyclohexylamine
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Ketone
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Hypoglycemic Agents
  • Sulfonylureas
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point188 - 190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.83e-02 g/LNot Available
LogP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.048 mg/mLALOGPS
logP1.72ALOGPS
logP1.81ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.31ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.77 m3·mol-1ChemAxon
Polarizability33.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00414
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00414
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00414
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1912
KEGG Compound IDC06806
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetohexamide
NuGOwiki LinkHMDB14558
Metagene LinkHMDB14558
METLIN IDNot Available
PubChem Compound1989
PDB IDNot Available
ChEBI ID28052
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
References
  1. Imamura Y, Shimada H: Differential pharmacokinetics of acetohexamide in male Wistar-Imamichi and Sprague-Dawley rats: role of microsomal carbonyl reductase. Biol Pharm Bull. 2005 Jan;28(1):185-7. [15635190 ]
  2. Imamura Y, Koga T, Higuchi T, Otagiri M, Sugino E, Hibino S: Inhibitory effect of drugs with a ketone group on reduction of acetohexamide catalyzed by carbonyl reductase from rabbit kidney. J Enzyme Inhib. 1997 Feb;11(4):285-92. [9208371 ]
  3. Kishimoto M, Kawamori R, Kamada T, Inaba T: Carbonyl reductase activity for acetohexamide in human erythrocytes. Drug Metab Dispos. 1994 May-Jun;22(3):367-70. [8070312 ]
General function:
Involved in inward rectifier potassium channel activity
Specific function:
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:
KCNJ1
Uniprot ID:
P48048
Molecular weight:
44794.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]