You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:16:26 UTC
HMDB IDHMDB0015252
Secondary Accession Numbers
  • HMDB15252
Metabolite Identification
Common NameGliclazide
DescriptionGliclazide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Gliclazide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Gliclazide is extensively metabolized by the liver; its metabolites are excreted in both urine (60-70%) and feces (10-20%).
Structure
Thumb
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
novo GliclazideMeSH
novo-GliclazideMeSH
Novopharm brand OF gliclazideMeSH
DiabrezideMeSH
Gen gliclazideMeSH
Servier brand OF gliclazideMeSH
Alphapharm brand OF gliclazideMeSH
DiaglykMeSH
DiaikronMeSH
DiamicronMeSH
Gen-gliclazideMeSH
Gliclazide servier brandMeSH
GlyadeMeSH
GlyclazideMeSH
Genpharm brand OF gliclazideMeSH
GliklazidMeSH
Helsinn brand OF gliclazideMeSH
Chemical FormulaC15H21N3O3S
Average Molecular Weight323.411
Monoisotopic Molecular Weight323.130362243
IUPAC Name1-(4-methylbenzenesulfonyl)-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea
Traditional Namegliclazide
CAS Registry Number21187-98-4
SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 g/LNot Available
LogP2.6Not 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-090u-9710000000-41d9060ced438af45b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0906000000-61b1e48114f8b1718b8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-72eec1bad0600cc00556View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017i-9200000000-13a3993b0b1cc083ea4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0918000000-260aeeb89b9404c56f7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-203f48d342734f8e7b9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05di-8900000000-db98ef26f5be17980cdaView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01120 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01120 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3356
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGliclazide
METLIN IDNot Available
PubChem Compound3475
PDB IDNot Available
ChEBI ID31654
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available