G2167
Gliclazide
powder, ≥98%
Synonym(s):
1-(3-Azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea
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About This Item
Empirical Formula (Hill Notation):
C15H21N3O3S
CAS Number:
Molecular Weight:
323.41
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352125
EC Number:
244-260-5
MDL number:
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Product Name
Gliclazide, powder, ≥98%
InChI key
BOVGTQGAOIONJV-UHFFFAOYSA-N
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)
SMILES string
Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2
assay
≥98%
form
powder
color
white
mp
163-169 °C (lit.)
solubility
methylene chloride: soluble
originator
Servier
Quality Level
Gene Information
human ... KCNJ1(3758)
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1 of 4
This Item | G3796 | SML0081 | SML0180 |
|---|---|---|---|
| form powder | form solid | form powder | form powder |
| assay ≥98% | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) |
| Quality Level 200 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| solubility methylene chloride: soluble | solubility H2O: >10 mg/mL | solubility H2O: ≥10 mg/mL | solubility H2O: ≥15 mg/mL at ~60 °C |
| color white | color white to off-white | color white to tan | color white to tan |
| originator Servier | originator Roche | originator Wyeth | originator - |
Application
Gliclazide has been used:
- to study its antiglycative properties and to study its effects on the glycation of bovine serum albumin (BSA) structure[1]
- 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[2]
- to develop and validate a simple, sensitive, rapid, economic and isocratic high-performance liquid chromatography (HPLC) method for the determination of gliclazide[3]
Used in the treatment of non-insulin dependent diabetes mellitus (NIDDM).
Biochem/physiol Actions
Gliclazide is Kir6.2/SUR1 channel inhibitor.
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
Features and Benefits
This compound was developed by Servier. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
Jane K McGavin et al.
Drugs, 62(9), 1357-1364 (2002-06-22)
Gliclazide modified release (MR) is a new formulation of the drug gliclazide and is given once daily. The hydrophilic matrix of hypromellose-based polymer in the new formulation effects a progressive release of the drug which parallels the 24-hour glycaemic profile
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