Glybenclamide (CHEM017485)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:23:36 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017485
Identification
Common NameGlybenclamide
ClassSmall Molecule
DescriptionGlyburide is a second generation sulfonylurea used to treat patients with diabetes mellitus type II. It is typically given to patients who cannot be managed with the standard first line therapy, . Glyburide stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations. Glyburide was granted FDA approval on 1 May 1984. A formulation with metformin was granted FDA approval on on 31 July 2000.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylureaChEBI
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylureaChEBI
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamideChEBI
DiabetaChEBI
GlibenclamidaChEBI
GlibenclamideChEBI
GlibenclamidumChEBI
GlynaseChEBI
MicronaseChEBI
1-((p-(2-(5-Chloro-O-anisamido)ethyl)phenyl)sulphonyl)-3-cyclohexylureaGenerator
1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulphonyl)-3-cyclohexylureaGenerator
5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulphonyl)phenyl)ethyl)-2-methoxybenzamideGenerator
Apo-glibenclamideHMDB
Euglucon 5HMDB
Euglucon NHMDB
GlybenclamideHMDB
NeogluconinHMDB
ManinilHMDB
DaonilHMDB
Chemical FormulaC23H28ClN3O5S
Average Molecular Mass494.004 g/mol
Monoisotopic Mass493.144 g/mol
CAS Registry Number10238-21-8
IUPAC Name5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide
Traditional Nameglyburide
SMILESCOC1=C(C=C(Cl)C=C1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
InChI IdentifierInChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
InChI KeyZNNLBTZKUZBEKO-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Benzenesulfonyl group
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Phenoxy compound
  • Chlorobenzene
  • Halobenzene
  • Sulfonylurea
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0021 g/LALOGPS
logP3.78ALOGPS
logP3.79ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity126.98 m³·mol⁻¹ChemAxon
Polarizability51.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9755200000-129e50286730bac1e4e1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0002190000-7f61119495ccea67ff2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lu-0594000000-78579410f8f6799b400bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lu-0594000000-78579410f8f6799b400bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ukc-2690000000-7afb48e267c7b334213bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dl-0901300000-a19ba3565aec1b9acb36Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0002290000-4a0641596c33a997d77eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0319000000-b4fc8ec2ce4cb2f7b9feSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0002190000-7f61119495ccea67ff2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-1629000000-bcf31c97391018018369Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2911000000-7c5e8a23fd392fd3eb4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0906000000-4ed189ce2c190cc04470Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-004i-3900000000-56a0233da7ea5ad5b008Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0009000000-e00bb352ba4f594be124Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0900000000-6741aab73ecc529efa18Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00b9-1900000000-4a4d0776263284e00e66Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0905000000-6ea41e91252175c31f91Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-014i-0900000000-1b775c20ef2ec84ca78aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0911000000-0cdcc11d3b177ada89a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0819000000-1d1b54a277888408f46cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-2209600000-84e7b22a56916b121823Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-8924000000-237d0276b5971a341e21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fv-9810000000-b29be4db2d87cad02005Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-3106900000-b388d1114dc8cc9dbee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gc4-2319000000-f708bea7c586cde056b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000y-9602000000-bac81070100f10ae3ae5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01016
HMDB IDHMDB0015151
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlibenclamide
Chemspider ID3368
ChEBI ID5441
PubChem Compound ID3488
Kegg Compound IDC07022
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Monami M, Luzzi C, Lamanna C, Chiasserini V, Addante F, Desideri CM, Masotti G, Marchionni N, Mannucci E: Three-year mortality in diabetic patients treated with different combinations of insulin secretagogues and metformin. Diabetes Metab Res Rev. 2006 Nov-Dec;22(6):477-82.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16081479
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20797618