G0326000
Gliclazide
European Pharmacopoeia (EP) Reference Standard
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
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
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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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Product No.
Description
Pricing
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
wgk_germany
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
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Gábor Winkler
Orvosi hetilap, 155(14), 541-548 (2014-04-01)
In addition to the common blood glucose lowering effect, sulfonylurea compounds are different in many aspects from each other. Based on earlier findings the second generation gliclazide has special advantages within this group. Although the number of experimental and clinical
Geneviève Renier et al.
Metabolism: clinical and experimental, 52(8 Suppl 1), 13-18 (2003-08-27)
Atherosclerotic cardiovascular disease is the leading cause of premature death in patients with diabetes. Atherosclerosis is a chronic immune-mediated disease, the initiation, progression, and destabilization of which is driven and regulated by inflammatory cells. One critical event in the initiation
Guntram Schernthaner
Metabolism: clinical and experimental, 52(8 Suppl 1), 29-34 (2003-08-27)
Gliclazide modified release (MR) is a new formulation of the drug gliclazide and is given once daily. The specifically designed hydrophilic matrix of gliclazide MR leads to a progressive drug release that parallels the 24-hour glycemic profile in type 2
G Crepaldi et al.
Metabolism: clinical and experimental, 49(10 Suppl 2), 21-25 (2000-11-15)
The constraints of intensive multifactorial management of type 2 diabetes dictate a need for effective, well-tolerated agents with simple administration regimens. Sulfonylureas remain the most frequently used agents, and represent a rational approach when consideration is given to the pathophysiology
[Non-insulin dependent diabetes. Role of gliclazide (diamicron)].
B Lesobre
Journees annuelles de diabetologie de l'Hotel-Dieu, 313-322 (1995-01-01)
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