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G2167

Sigma-Aldrich

Gliclazide

powder, ≥98%

Synonym(s):
1-(3-Azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea
Empirical Formula (Hill Notation):
C15H21N3O3S
CAS Number:
Molecular Weight:
323.41
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

form

powder

color

white

mp

163-169 °C (lit.)

solubility

methylene chloride: soluble

originator

Servier

SMILES string

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)

InChI key

BOVGTQGAOIONJV-UHFFFAOYSA-N

Gene Information

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).

Packaging

5 g in poly bottle

Biochem/physiol Actions

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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