G2167
Gliclazide
powder, ≥98%
Synonyme(s) :
1-(3-Azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea
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About This Item
Formule empirique (notation de Hill):
C15H21N3O3S
Numéro CAS:
Poids moléculaire :
323.41
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352125
ID de substance PubChem :
Nomenclature NACRES :
NA.77
Produits recommandés
Pureté
≥98%
Forme
powder
Couleur
white
Pf
163-169 °C (lit.)
Solubilité
methylene chloride: soluble
Auteur
Servier
Chaîne SMILES
Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2
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)
Clé InChI
BOVGTQGAOIONJV-UHFFFAOYSA-N
Informations sur le gène
human ... KCNJ1(3758)
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Application
Gliclazide has been used:
- to study its antiglycative properties and to study its effects on the glycation of bovine serum albumin (BSA) structure
- as a reference standard in solid-phase extraction (SPE) followed by instrumental analysis using liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) for the quantification of water samples
- to develop and validate a simple, sensitive, rapid, economic and isocratic high-performance liquid chromatography (HPLC) method for the determination of gliclazide
Used in the treatment of non-insulin dependent diabetes mellitus (NIDDM).
Actions biochimiques/physiologiques
Oxidative modification of low-density lipoprotein (LDL) plays an important role in vascular dysfunction associated with diabetes mellitus. Gliclazide is a second-generation sulfonylurea with free-radical-scavenging activity. Incubation of human aortic smooth muscle cell (HASMC) with native human LDL (100 μg/mL) in the presence of increasing concentrations of gliclazide (1 to 10 μg/mL) resulted in a dose-dependent decrease in HASMC-mediated LDL oxidation. Exposure of HASMCs to gliclazide (1 to 10 μg/mL) and native LDL (100 μg/mL) also led to a dose-dependent decrease in oxidized LDL-induced human monocyte adhesion to HASMCs. In addition, incubation of HASMCs with gliclazide dramatically reduced the ability of oxidized LDL to stimulate the proliferation of these cells. Finally, treatment of HASMCs with gliclazide resulted in a marked decrease in oxidatively modified LDL-induced monocyte chemoattractant protein (MCP)-1 and human heat shock protein 70 (HSP 70) expression, both at the gene and protein levels. These results show that gliclazide, at concentrations in the therapeutic range (5 to 10 μg/mL), is effective in vitro in reducing vascular smooth muscle cell (VSMC) dysfunction induced by oxidatively modified LDL. Administration of gliclazide to type 2 diabetic patients could form part of the strategy for the prevention and management of diabetic cardiovascular diseases
Caractéristiques et avantages
This compound was developed by Servier. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
Mention d'avertissement
Warning
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 4 Oral
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 2
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
Eyeshields, Gloves, type N95 (US)
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Les clients ont également consulté
Ewa Żurawska-Płaksej et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 189, 625-633 (2017-09-10)
Albumin, the major serum protein, plays a variety of functions, including binding and transporting endogenous and exogenous ligands. Its molecular structure is sensitive to different environmental modifiers, among which glucose is one of the most significant. In vivo albumin glycation
Ahmed Gedawy et al.
Journal of food and drug analysis, 27(1), 315-322 (2019-01-17)
An efficient and simple HPLC method has been developed and validated for the simultaneous determination of gliclazide and metformin hydrochloride in bulk and was applied on marketed metformin and gliclazide products. The mobile phase used for the chromatographic runs consisted
Development and validation of a new analytical HPLC method for simultaneous determination of the antidiabetic drugs, metformin and gliclazide
Gedawy GA, et al.
Journal of food and drug analysis, 27(1), 315-322 (2019)
Martin Javorsky et al.
European journal of internal medicine, 23(3), 245-249 (2012-03-06)
Potassium inwardly rectifier 6.2 subunit (Kir6.2) of the ATP-sensitive potassium (K(ATP)) channel encoded by KCNJ11 gene is a therapeutical target for sulfonylureas. KCNJ11 E23K polymorphism was associated with type 2 diabetes in genetic association studies. The aim of the present
D N Juurlink et al.
Diabetic medicine : a journal of the British Diabetic Association, 29(12), 1524-1528 (2012-08-24)
Sulphonylureas promote insulin release by inhibiting pancreatic potassium channels. Older sulphonylureas such as glyburide (glibenclamide), but not newer ones such as gliclazide, antagonize similar channels in myocardium, interfering with the protective effects of ischaemic preconditioning. Whether this imparts a higher
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