Glybenclamide (CED0003265)

Record Information
Version1.0
Creation Date2016-05-22 04:23:36 UTC
Update Date2026-08-22 01:02:43 UTC
Accession NumberCHEM017485
Identification
Common NameGlybenclamide
ClassSmall Molecule
Description
Glybenclamide is an organic compound with the formula C23H28ClN3O5S and an average molecular weight of 494.00 g/mol. Glybenclamide belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from 30 sources, including drinking water, ladders, and household cleaning and consumer products such as perfumes within detergents and soaps, ash trays, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Other sources include food, food processing and cookware—specifically food preservation, processing meats, fermentation processes for beer, the preparation of vinegar, and the preparation of wort—as well as electrical and electronic equipment including antennas, auxiliary devices, electric switches, conductive bodies characterised by the conductive materials, and cores yokes or armatures. Additionally, it is found in healthcare, pharmaceuticals and veterinary products as blood glucose lowering drugs, excluding insulins. The recorded exposure route is oral. The compound interacts with nine protein targets, acting as an antagonist, inhibitor, or modulator of the ATP-binding cassette sub-family C member 9 (ABCC9), the bile salt export pump (ABCB11), the phospholipid-transporting ATPase ABCA1, the cystic fibrosis transmembrane conductance regulator (CFTR), and five other proteins. In terms of health effects, glybenclamide is used as a treatment for diabetes mellitus (PMC4285261), type 2 diabetes mellitus (PMC10904444), gestational diabetes (PMC5384842), and edema (PMC11832355). It further exhibits therapeutic effects on inflammation (PMC6329030) and hyperglycemia (PMC11127218).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
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
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 Solubility0.0021 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-9755200000-129e50286730bac1e4e1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0002190000-7f61119495ccea67ff2fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-0594000000-78579410f8f6799b400bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lu-0594000000-78579410f8f6799b400bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ukc-2690000000-7afb48e267c7b334213bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-0901300000-a19ba3565aec1b9acb36Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0002290000-4a0641596c33a997d77eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0319000000-b4fc8ec2ce4cb2f7b9feNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0002190000-7f61119495ccea67ff2fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1629000000-bcf31c97391018018369Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2911000000-7c5e8a23fd392fd3eb4dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0906000000-4ed189ce2c190cc04470Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-3900000000-56a0233da7ea5ad5b008Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-e00bb352ba4f594be124Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-6741aab73ecc529efa18Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00b9-1900000000-4a4d0776263284e00e66Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0905000000-6ea41e91252175c31f91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-1b775c20ef2ec84ca78aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0911000000-0cdcc11d3b177ada89a9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0819000000-1d1b54a277888408f46cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01t9-9800000000-236b81d2305f4333285fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-0009500000-d4d409f26d8a32a6638dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-7c537167b4b225ae3223Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0906000000-b0a2e55d2ca3cfb6f5f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-0901400000-948ee68011e134082842Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-2900000000-251eafded18f4909f168Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0001900000-1ea806a1b04ce45ffec2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0901000000-b54a0c69e1ec6e725fa9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01bc-0609700000-055b1966e0ef69a5812cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0901000000-e32c83f8a1b71a5382d1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-925357264e8ea7a2e835Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-0104900000-d07b191e3b14aeb9f1c9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-1c42c66787b15b1bdfb7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-72b51801999ee6e8ba2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-3b46ceac71502b867c5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-2209600000-84e7b22a56916b121823Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-8924000000-237d0276b5971a341e21Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fv-9810000000-b29be4db2d87cad02005Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-3106900000-b388d1114dc8cc9dbee1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gc4-2319000000-f708bea7c586cde056b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000y-9602000000-bac81070100f10ae3ae5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-0406900000-487073d881e5683f5de1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0319000000-4c5406a8c76a9fcccbfcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-1911100000-36baf612957d01a4d5e9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0000900000-e4535e4dc8592be8999aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9000000000-c2fa753da65a4bac80a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9111100000-4cdd49b8f1196d6aa698Not 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
8870.0Log mg/kg[5000:16000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC6329030
type 2 diabetes mellitusis_treatment_forNot AvailablePMC10904444
gestational diabetesis_treatment_forNot AvailablePMC5384842 , PMC5384842
diabetes mellitusis_treatment_forNot AvailablePMC4285261
edemais_treatment_forNot AvailablePMC11832355
hyperglycemiahas_therapeutic_effect_onNot AvailablePMC11127218
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
498LaddersBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q8R4B8Mus musculusPredicted (SEA)0.155698
NACHT, LRR and PYD domains-containing protein 3 structureClick to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q96P20HumansPredicted (SEA)0.233548
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)14.7135
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)74.1903
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)2.88042
Click to view 3D structureD(2) dopamine receptorQ9GJU1Canis lupus familiarisPredicted (SEA)2.49118
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)97.9343
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)159.513
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)182.868
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)249.273
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)6.07224
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)86.6462
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)58.3091
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)86.2569
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)30.439
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)112.259
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)40.3259
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)44.6076
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)184.892
Click to view 3D structureProstaglandin E receptor 4Q9TU16Canis lupus familiarisPredicted (SEA)0.389246
CDGSH iron-sulfur domain-containing protein 1 structureClick to view 3D structureCDGSH iron-sulfur domain-containing protein 1Q9NZ45HumansPredicted (SEA)4.82665
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)24.289
Click to view 3D structureSolute carrier family 22 member 6O35956Rattus norvegicusPredicted (SEA)0.155698
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)71.777
Click to view 3D structure5-hydroxytryptamine receptor 4Q62758Rattus norvegicusPredicted (SEA)16.5819
Concentrations
Not Available
External Links
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