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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014558
Secondary Accession Numbers
  • HMDB14558
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
Data?1582753193
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
GamadiabetHMDB
Lilly brand OF acetohexamideHMDB
Salvat brand OF acetohexamideHMDB
DimelorHMDB
Acetohexamide lilly brandHMDB
Acetohexamide salvat brandHMDB
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 KeyVGZSUPCWNCWDAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Benzenesulfonamide
  • Acetophenone
  • Benzenesulfonyl group
  • Benzoyl
  • Aryl alkyl ketone
  • Sulfonylurea
  • Benzenoid
  • Monocyclic benzene moiety
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 - 190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.048 g/LNot Available
LogP2.7Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available178.186http://allccs.zhulab.cn/database/detail?ID=AllCCS00001322
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.77 m³·mol⁻¹ChemAxon
Polarizability33.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.65831661259
DarkChem[M-H]-172.2631661259
DeepCCS[M+H]+172.64530932474
DeepCCS[M-H]-170.2530932474
DeepCCS[M-2H]-203.64130932474
DeepCCS[M+Na]+178.83730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetohexamideCC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC14132.0Standard polar33892256
AcetohexamideCC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC12401.1Standard non polar33892256
AcetohexamideCC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC12849.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetohexamide,1TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C12864.4Semi standard non polar33892256
Acetohexamide,1TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C12598.6Standard non polar33892256
Acetohexamide,1TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C)C=C13845.9Standard polar33892256
Acetohexamide,1TMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C12844.9Semi standard non polar33892256
Acetohexamide,1TMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C12672.3Standard non polar33892256
Acetohexamide,1TMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C)C=C13783.3Standard polar33892256
Acetohexamide,2TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C12749.9Semi standard non polar33892256
Acetohexamide,2TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C12832.9Standard non polar33892256
Acetohexamide,2TMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C)[Si](C)(C)C)C=C13601.4Standard polar33892256
Acetohexamide,1TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C13139.8Semi standard non polar33892256
Acetohexamide,1TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C12829.8Standard non polar33892256
Acetohexamide,1TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)NC2CCCCC2)[Si](C)(C)C(C)(C)C)C=C13901.0Standard polar33892256
Acetohexamide,1TBDMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C13104.7Semi standard non polar33892256
Acetohexamide,1TBDMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C12935.7Standard non polar33892256
Acetohexamide,1TBDMS,isomer #2CC(=O)C1=CC=C(S(=O)(=O)NC(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)C=C13829.6Standard polar33892256
Acetohexamide,2TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13314.2Semi standard non polar33892256
Acetohexamide,2TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13324.6Standard non polar33892256
Acetohexamide,2TBDMS,isomer #1CC(=O)C1=CC=C(S(=O)(=O)N(C(=O)N(C2CCCCC2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C13655.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetohexamide EI-B (Non-derivatized)splash10-03di-8390000000-581eca2d35a4f5f0362a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetohexamide EI-B (Non-derivatized)splash10-0a5c-9200000000-09e03cfa3bf5df8c2b452017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetohexamide EI-B (Non-derivatized)splash10-03di-8390000000-581eca2d35a4f5f0362a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetohexamide EI-B (Non-derivatized)splash10-0a5c-9200000000-09e03cfa3bf5df8c2b452018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetohexamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9762000000-4ab556868f4c484f31f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetohexamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetohexamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 45V, Negative-QTOFsplash10-001i-0900000000-ade329597c8f14b5b16a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 30V, Negative-QTOFsplash10-0002-0900000000-1e17946b498a6c3dba352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 90V, Positive-QTOFsplash10-0006-7920000000-a673d7d17d313e8faeb02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 15V, Negative-QTOFsplash10-00di-0409000000-f64a52fc103bd9277ac02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 30V, Positive-QTOFsplash10-0089-2960000000-e3b789e7fdffc4c5a0102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 45V, Positive-QTOFsplash10-001i-0900000000-692de6e4fa6b4c8e028f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 15V, Positive-QTOFsplash10-0006-0090000000-56d55252bc4e05cbe95e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 45V, Positive-QTOFsplash10-00ea-3930000000-678ffa21bcc7c05f26a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 75V, Positive-QTOFsplash10-0006-9820000000-1417669e6b52bf6b75d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 30V, Positive-QTOFsplash10-0089-2960000000-7226ad20cc1145237f1b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 60V, Negative-QTOFsplash10-001i-1900000000-202cc47e379cad6532ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 90V, Negative-QTOFsplash10-000x-9400000000-bf97dd09118468c2094c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 45V, Positive-QTOFsplash10-00ea-3930000000-8fba47ba7df0b91c576d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetohexamide 75V, Negative-QTOFsplash10-001l-5900000000-64f67d5201d487a69c312021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 10V, Positive-QTOFsplash10-0fb9-3159000000-4eeeef390be45695b6c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 20V, Positive-QTOFsplash10-0uea-9360000000-0dae629411a247177e472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 40V, Positive-QTOFsplash10-00sm-9100000000-c6662fd8a67d452b57a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 10V, Negative-QTOFsplash10-00dj-3349000000-575f9836791a435b12332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 20V, Negative-QTOFsplash10-0002-2950000000-52036d3d328239f8e10a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 40V, Negative-QTOFsplash10-0002-9610000000-39f088fc65ab8f5701da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 10V, Negative-QTOFsplash10-00dj-0809000000-8202a0bfd064f33e94d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 20V, Negative-QTOFsplash10-0002-2904000000-f88244a51de7c93e29022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 40V, Negative-QTOFsplash10-0006-9400000000-c00a12699f3212b791cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 10V, Positive-QTOFsplash10-0006-0192000000-706cb326d1b8d0a523f82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetohexamide 20V, Positive-QTOFsplash10-00o0-2931000000-81b94a64fe32c596118a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00414 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00414 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00414
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1912
KEGG Compound IDC06806
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetohexamide
METLIN IDNot Available
PubChem Compound1989
PDB IDNot Available
ChEBI ID28052
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:17016423 ]