GLICLAZIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H21N3O3S
Molecular Weight	323.411
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CCC[C@]1([H])CN(C2)NC(=O)NS(=O)(=O)C3=CC=C(C)C=C3

InChI

InChIKey=BOVGTQGAOIONJV-BETUJISGSA-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)/t12-,13+

HIDE SMILES / InChI

Molecular Formula	C15H21N3O3S
Molecular Weight	323.411
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Gliclazide (BILXONA®) is an oral sulfonylurea hypoglycemic agent which is used in type 2 diabetes to stimulate insulin production. It differs from other related compounds by an N-containing heterocyclic ring with an endocyclic bond. Gliclazide (BILXONA®) reduces blood glucose levels by stimulating insulin secretion from the beta-cells of the islets of Langerhans. Increase in postprandial insulin and C-peptide secretion persists after two years of treatment. In addition to these metabolic properties, Gliclazide (BILXONA®) has haemovascular properties. It is not available for sale in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
potassium inwardly rectifying channel, subfamily J, member 11 1	Inhibitor 8,297		3.0 mM [Ki]
ATP-binding cassette sub-family C member 8 3	Inhibitor 8,297		50.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259	Primary		Approved 8,429	BILXONA

PubMed

Show entries

Title	Date	PubMed
Gliclazide-induced acute hepatitis.	2000 Jan	10656221
Comparison of acarbose and gliclazide as first-line agents in patients with type 2 diabetes.	2001	11268714
Glibenclamide vs gliclazide in reducing oxidative stress in patients of noninsulin dependent diabetes mellitus--a double blind randomized study.	2001 Aug	11837468
Regulation of glucose transporter 1 expression by gliclazide in rat L6 myoblasts.	2001 Dec	11853362
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.	2001 Feb	11174074

Showing 1 to 5 of 25 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The daily dose may vary from 1 to 4 tablets per day, i.e. from 30 to 120 mg taken orally in a single intake at breakfast time.

Route of Administration: Oral

In Vitro Use Guide

Gliclazide blocked whole-cell murine beta-cell Katp currents with an IC50 of 184 +/- 30 nmol/l (n = 6-10) but was much less effective in rat cardiac and smooth muscle (IC50s of 19.5 +/- 5.4 micromol/l (n = 6-12) and 37.9 +/- 1.0 micromol/l (n = 5-10), respectively). In all three tissues, the action of the drug on whole-cell Katp currents was rapidly reversible. In inside-out patches on beta-cells, gliclazide (1 micromol/l) produced a maximum of 66 +/- 13 % inhibition (n = 5), compared with more than 98 % block in the whole-cell configuration.