Gliclazide (CED0003855)

Record Information
Version1.0
Creation Date2016-05-22 03:41:24 UTC
Update Date2026-08-19 11:53:12 UTC
Accession NumberCHEM016720
Identification
Common NameGliclazide
ClassSmall Molecule
Description
Gliclazide is an organic compound with the chemical formula C15H21N3O3S and an average molecular weight of 323.41 g/mol. Gliclazide belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. This compound is identified as being found in or released from 11 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with gynecologicals and blood glucose lowering drugs, excluding insulins. Other sources include food preservation in food, food processing, and cookware; indoor air in air, dust, and atmospheric transport; and non-electric simulated smoking devices and tobacco smoke filters in household cleaning and consumer products. Additionally, it is linked to electrical and electronic equipment, specifically electrodes, television systems, gas filled discharge tubes with solid cathode, discharge lamps, and electrically stimulated smoking devices. Recorded exposure routes for the substance include oral and inhalation. In terms of biological activity, two protein targets have been recorded for Gliclazide. It acts as a binder or otherwise unknown interactor of ATP-binding cassette sub-family C member 8 (ABCC8) and is also associated with Vascular endothelial growth factor A, long form (VEGFA).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)ureaChEBI
1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)ureaChEBI
GlimicronChEBI
1-(3-Azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulphonyl)ureaGenerator
1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulphonyl)ureaGenerator
N-(4-Methylbenzenesulfonyl)-n'-(3-azabicyclo(3.3.0)oct-3-yl)ureaHMDB
Generics brand OF gliclazideMeSH, HMDB
novo GliclazideMeSH, HMDB
novo-GliclazideMeSH, HMDB
Novopharm brand OF gliclazideMeSH, HMDB
DiabrezideMeSH, HMDB
Gen gliclazideMeSH, HMDB
Servier brand OF gliclazideMeSH, HMDB
Alphapharm brand OF gliclazideMeSH, HMDB
DiaglykMeSH, HMDB
DiaikronMeSH, HMDB
DiamicronMeSH, HMDB
Gen-gliclazideMeSH, HMDB
Gliclazide servier brandMeSH, HMDB
GlyadeMeSH, HMDB
GlyclazideMeSH, HMDB
Genpharm brand OF gliclazideMeSH, HMDB
GliklazidMeSH, HMDB
Helsinn brand OF gliclazideMeSH, HMDB
Chemical FormulaC15H21N3O3S
Average Molecular Mass323.411 g/mol
Monoisotopic Mass323.130 g/mol
CAS Registry Number21187-98-4
IUPAC Name1-(4-methylbenzenesulfonyl)-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea
Traditional Namegliclazide
SMILESCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1
InChI IdentifierInChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)
InChI KeyBOVGTQGAOIONJV-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
  • Tosyl compound
  • Benzenesulfonyl group
  • Toluene
  • Sulfonylurea
  • Pyrrolidine
  • Semicarbazide
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Carbonic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.19 g/LALOGPS
logP1.52ALOGPS
logP1.73ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)1.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.51 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.88 m³·mol⁻¹ChemAxon
Polarizability34.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-090u-9710000000-41d9060ced438af45b28Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0906000000-61b1e48114f8b1718b8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-72eec1bad0600cc00556Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-017i-9200000000-13a3993b0b1cc083ea4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0918000000-260aeeb89b9404c56f7cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-203f48d342734f8e7b9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05di-8900000000-db98ef26f5be17980cdaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0509000000-7b4a79b4b48ae80c7b43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03kc-4902000000-cd8eecee62c14a855d43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-5d783afa0afef9e90b80Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0109000000-073e1f26bf7df99de658Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-6c0a8c8143980bba7095Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-6910000000-e3926c03e36a20a9165bNot 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
2192.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
263Blood glucose lowering drugs, excl. insulinsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)416.182
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)125.182
Click to view 3D structureProstaglandin E receptor 4Q9TU16Canis lupus familiarisPredicted (SEA)0.389246
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)147.914
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)325.098
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)276.209
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)164.028
NACHT, LRR and PYD domains-containing protein 3 structureClick to view 3D structureNACHT, LRR and PYD domains-containing protein 3Q96P20HumansPredicted (SEA)16.1148
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)140.362
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)886.236
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)462.891
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)374.377
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)544.711
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)1055.25
Mucolipin-1 structureClick to view 3D structureMucolipin-1Q9GZU1HumansPredicted (SEA)7.47353
Mucolipin-3 structureClick to view 3D structureMucolipin-3Q8TDD5HumansPredicted (SEA)8.09632
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2705.26
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)262.819
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)508.978
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)463.047
Sentrin-specific protease 8 structureClick to view 3D structureSentrin-specific protease 8Q96LD8HumansPredicted (SEA)67.7288
Thromboxane A2 receptor structureClick to view 3D structureThromboxane A2 receptorP21731HumansPredicted (SEA)119.265
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)2283.08
Click to view 3D structureProstaglandin E2 receptor EP1 subtypeP34995HumansPredicted (SEA)128.918
Prostaglandin E2 receptor EP3 subtype structureClick to view 3D structureProstaglandin E2 receptor EP3 subtypeP43115HumansPredicted (SEA)146.512
Concentrations
Not Available
External Links
DrugBank IDDB01120
HMDB IDHMDB0259579
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGliclazide
Chemspider ID3356
ChEBI ID31654
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10048179
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14871415
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16631804
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22118706
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22183301
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22411174
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22732450
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=9226746