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G0326000

Gliclazide

European Pharmacopoeia (EP) Reference Standard

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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:
PubChem Substance ID:
NACRES:
NA.24

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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This Item
BP368PHR1288G0326012
Gliclazide European Pharmacopoeia (EP) Reference Standard

G0326000

Gliclazide

Gliclazide British Pharmacopoeia (BP) Reference Standard

BP368

Gliclazide

Gliclazide Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1288

Gliclazide

vibrant-m

G0326012

Gliclazide impurity F

manufacturer/tradename

EDQM

manufacturer/tradename

BP

manufacturer/tradename

-

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

format

neat

format

neat

format

neat

format

neat

API family

gliclazide

API family

gliclazide

API family

gliclazide

API family

gliclazide

mp

163-169 °C (lit.)

mp

163-169 °C (lit.)

mp

-

mp

-

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
O Ziegler et al.
Journal of diabetes and its complications, 8(4), 235-239 (1994-10-01)
Non-insulin-dependent diabetes mellitus (NIDDM) is associated with an increased risk of macro- and microvascular degenerative complications. Gliclazide is a second generation sulfonylurea that is widely used in the treatment of type II diabetes mellitus. Its hypoglycemic activity is well documented.
K G Alberti
Diabete & metabolisme, 20(3 Pt 2), 341-348 (1994-11-01)
Gliclazide is a second-generation sulfonylures that is widely used in the treatment of non-insulin-dependent diabetes mellitus (Type 2 diabetes). It has been recommended for use on the basis of both its metabolic and nonmetabolic effects. It has a clear beneficial
P E Jennings
Journal of diabetes and its complications, 8(4), 226-230 (1994-10-01)
Patients with type II diabetes commonly die from thrombotic vascular disease. Large vessel occlusion due to thrombosis or atherosclerotic stenosis is a process accelerated by diabetes and results in premature death. Diabetic small vessel disease, with its unique microangiopathic process

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