Acetohexamide (CED0011418)

Record Information
Version1.0
Creation Date2016-05-22 03:23:15 UTC
Update Date2026-08-19 11:37:10 UTC
Accession NumberCHEM016217
Identification
Common NameAcetohexamide
ClassSmall Molecule
Description
Acetohexamide is an organic compound with the chemical formula C15H20N2O4S and an average molecular weight of 324.39 g/mol. Acetohexamide belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. The compound is found in or released from nine recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is associated with gynecologicals and blood glucose lowering drugs, excluding insulins. It is also found in food preservation within food, food processing, and cookware. Other recorded sources include household cleaning and consumer products, specifically tobacco smoke filters, perfumes within detergents and soaps, and non-electric simulated smoking devices. Additionally, it is released from electrical and electronic equipment, including electrically stimulated smoking devices, television systems, and electric switches. The recorded exposure route for this compound is oral. At the molecular level, acetohexamide interacts with two recorded protein targets. It acts as an inhibitor or modulator of the ATP-sensitive inward rectifier potassium channel 1 (KCNJ1) and the ATP-binding cassette sub-family C member 8 (ABCC8).
Contaminant TypeNot Available
Chemical Structure
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 Mass324.395 g/mol
Monoisotopic Mass324.114 g/mol
CAS Registry Number968-81-0
IUPAC Name3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea
Traditional Nameacetohexamide
SMILESCC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-03di-8390000000-581eca2d35a4f5f0362aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a5c-9200000000-09e03cfa3bf5df8c2b45Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03di-8390000000-581eca2d35a4f5f0362aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a5c-9200000000-09e03cfa3bf5df8c2b45Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-9762000000-4ab556868f4c484f31f6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-ade329597c8f14b5b16aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-1e17946b498a6c3dba35Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-7920000000-a673d7d17d313e8faeb0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0409000000-f64a52fc103bd9277ac0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0089-2960000000-e3b789e7fdffc4c5a010Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-692de6e4fa6b4c8e028fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-56d55252bc4e05cbe95eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ea-3930000000-678ffa21bcc7c05f26a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9820000000-1417669e6b52bf6b75d4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0089-2960000000-7226ad20cc1145237f1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-202cc47e379cad6532abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-9400000000-bf97dd09118468c2094cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ea-3930000000-8fba47ba7df0b91c576dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001l-5900000000-64f67d5201d487a69c31Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fb9-3159000000-4eeeef390be45695b6c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uea-9360000000-0dae629411a247177e47Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00sm-9100000000-c6662fd8a67d452b57a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-3349000000-575f9836791a435b1233Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2950000000-52036d3d328239f8e10aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9610000000-39f088fc65ab8f5701daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-0809000000-8202a0bfd064f33e94d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2904000000-f88244a51de7c93e2902Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9400000000-c00a12699f3212b791cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0192000000-706cb326d1b8d0a523f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00o0-2931000000-81b94a64fe32c596118aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f8c-9820000000-1ff37498a3deb8153b10Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2400.0Log mg/kg[1300:4300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureEpoxide hydrolase 1P07099HumansPredicted (SEA)5.29375
Click to view 3D structureEpoxide hydrolase 1Q9D379Mus musculusPredicted (SEA)1.47914
Bifunctional epoxide hydrolase 2 structureClick to view 3D structureBifunctional epoxide hydrolase 2P34913HumansPredicted (SEA)22.187
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)650.508
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)92.1735
Click to view 3D structureBifunctional epoxide hydrolase 2P34914Mus musculusPredicted (SEA)28.9599
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)220.936
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)335.608
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)319.338
NACHT, LRR and PYD domains-containing protein 3 structureClick to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q96P20HumansPredicted (SEA)15.3363
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)356.549
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)193.3
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)148.848
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)146.512
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)433.309
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)162.082
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)829.561
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)346.585
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)402.169
Suppressor of tumorigenicity 14 protein structureClick to view 3D structureSuppressor of tumorigenicity 14 proteinQ9Y5Y6HumansPredicted (SEA)216.032
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)176.951
RAF proto-oncogene serine/threonine-protein kinase structureClick to view 3D structureRAF proto-oncogene serine/threonine-protein kinaseP04049HumansPredicted (SEA)624.351
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)330.626
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)99.4135
Click to view 3D structureS-formylglutathione hydrolaseQ9GJT2Sus scrofaPredicted (SEA)7.47353
Concentrations
Not Available
External Links
DrugBank IDDB00414
HMDB IDHMDB0014558
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetohexamide
Chemspider ID1912
ChEBI ID28052
PubChem Compound ID1989
Kegg Compound IDC06806
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13945057
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2699749
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8070312
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=910864