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Gliclazide

July 24, 2017
Common Name

Gliclazide Description

Gliclazide is an oral antihyperglycemic agent used for the treatment of non-insliin-dependent diabetes mellitus (NIDDM). It belongs to the slifonylurea class of insliin secretagogues, which act by stimliating β cells of the pancreas to release insliin. Slifonylureas increase both basal insliin secretion and meal-stimliated insliin 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. Slifonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insliin receptors. Slifonylureas are associated with weight gain, though less so than insliin. Due to their mechanism of action, slifonylureas 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-(3-azabicyclo(3.3.0)Oct-3-yl)-3-(P-tolylslifonyl)ureaChEBI 1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(P-tolylslifonyl)ureaChEBI GlimicronChEBI 1-(3-azabicyclo(3.3.0)Oct-3-yl)-3-(P-tolylsliphonyl)ureaGenerator 1-(Hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(P-tolylsliphonyl)ureaGenerator N-(4-Methylbenzeneslifonyl)-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 Formlia

C15H21N3O3S Average Molecliar Weight

323.411 Monoisotopic Molecliar Weight

323.130362243 IUPAC Name

1-(4-methylbenzeneslifonyl)-3-{octahydrocyclopenta[c]pyrrol-2-yl}urea Traditional Name

gliclazide CAS Registry Number

21187-98-4 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 Key

BOVGTQGAOIONJV-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzeneslifonamides. These are organic compounds containing a slifonamide group that is S-linked to a benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Benzeneslifonamides Alternative Parents

  • Tosyl compounds
  • Benzeneslifonyl compounds
  • Slifonylureas
  • Semicarbazides
  • Pyrrolidines
  • Organoslifonic acids and derivatives
  • Aminoslifonyl compounds
  • Organic carbonic acids and derivatives
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Benzeneslifonamide
  • Tosyl compound
  • Benzeneslifonyl group
  • Toluene
  • Slifonylurea
  • Pyrrolidine
  • Semicarbazide
  • Organic slifonic acid or derivatives
  • Aminoslifonyl compound
  • Slifonyl
  • Organoslifonic acid or derivatives
  • Carbonic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organoslifur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • N-slifonylurea (CHEBI:31654 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antidiabetic
  • Hypoglycemic Agents
  • Slifonylureas

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point181 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.90e-01 g/LNot Available LogP2.6Not Available

    Predicted Properties

    Property Value Source Water Solubility0.19 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity83.88 m3·mol-1ChemAxon Polarizability34.22 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Gliclazide PathwaySMP00461Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01120

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01120

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01120 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    3356 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Gliclazide NuGOwiki Link

    HMDB15252 Metagene Link

    HMDB15252 METLIN ID

    Not Available PubChem Compound

    3475 PDB ID

    Not Available ChEBI ID

    31654

    Product: 6-TAMRA

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 10336422

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