G0326000
Gliclazide
European Pharmacopoeia (EP) Reference Standard
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All Photos(1)
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
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
grade
pharmaceutical primary standard
API family
gliclazide
manufacturer/tradename
EDQM
mp
163-169 °C (lit.)
application(s)
pharmaceutical (small molecule)
format
neat
storage temp.
2-8°C
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
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General description
This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.
Application
Used in the treatment of non-insulin dependent diabetes mellitus (NIDDM).
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
Packaging
The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.
Other Notes
Sales restrictions may apply.
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Description
Pricing
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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
[Glycogen synthetase and non-insulin-dependent diabetes: role of gliclazide].
B Lesobre
Journees annuelles de diabetologie de l'Hotel-Dieu, 315-321 (1991-01-01)
Metabolic approach to atherosclerosis: effect of gliclazide.
D N Brindley
Metabolism: clinical and experimental, 41(5 Suppl 1), 20-24 (1992-05-01)
K J Palmer et al.
Drugs, 46(1), 92-125 (1993-07-01)
Gliclazide is a second generation sulphonylurea oral hypoglycaemic agent used in the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It improves defective insulin secretion and may reverse insulin resistance observed in patients with NIDDM. These actions are reflected in a reduction
A Harrower
Metabolism: clinical and experimental, 49(10 Suppl 2), 7-11 (2000-11-15)
Although sulfonylureas have been used for more than 40 years, it is only recently that their molecular mechanisms of action have been elucidated. Gliclazide modified release, whose introduction comes soon after the sequencing and cloning of the sulfonylurea receptor, is
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