GLICLAZIDE

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

Structure Search

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

Description
Sources: http://www.medicines.org.uk/emc/medicine/31089
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68005907 | https://www.drugs.com/cons/gliclazide.html

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 Target ID: 16514.0 Gene Symbol: Kcnj11 Sources: https://www.drugbank.ca/drugs/DB01120	Inhibitor 8297		3.0 mM [Ki]
ATP-binding cassette sub-family C member 8 3 Target ID: CHEMBL1944490 Sources: https://www.drugbank.ca/drugs/DB01120	Inhibitor 8297		50.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: http://www.medicines.org.uk/emc/medicine/31089	Primary		Approved 8429	BILXONA Approved Use Non insulin-dependent diabetes (type 2) in adults when dietary measures, physical exercise and weight loss alone are not sufficient to control blood glucose. Launch Date 2015

PubMed

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
Gliclazide mainly affects insulin secretion in second phase of type 2 diabetes mellitus.	2001 Jun	11456286
Gliclazide decreases vascular smooth muscle cell dysfunction induced by cell-mediated oxidized low-density lipoprotein.	2001 Jun	11398146
[Toxicological analysis in the dawn of the third millenium].	2001 Sep-Oct	11602391
High-frequency insulin pulsatility and type 2 diabetes: from physiology and pathophysiology to clinical pharmacology.	2002 Dec	12703061
Sulfonylurea stimulation of insulin secretion.	2002 Dec	12475777
Does gliclazide stimulate first-phase, second-phase, or both phases of insulin release?	2002 Feb	11972296
Adenosine triphosphate-sensitive potassium (K(ATP)) channel activity is coupled with insulin resistance in obesity and type 2 diabetes mellitus.	2002 Feb	11868613
Oral hypoglycaemic agent failure.	2002 Jul	12674170
Bioequivalence evaluation of two brands of gliclazide 80 mg tablets (Glyzide & Diamicron)--in healthy human volunteers.	2002 Jul	12116051
Complete bioavailability and lack of food-effect on pharmacokinetics of gliclazide 30 mg modified release in healthy volunteers.	2002 May	12015789
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus].	2003	14570054
Addition of rosiglitazone to existing sulfonylurea treatment in chinese patients with type 2 diabetes and exposure to hepatitis B or C.	2003	12725705
Study of the solubilization of gliclazide by aqueous micellar solutions.	2003 Apr	12661069
Severe relapsing sulphonylurea-induced hypoglycaemia: a diagnostic and therapeutic challenge.	2003 Feb	12612336
The application of the convective diffusion model and the film equilibrium model to surfactant-facilitated dissolution of gliclazide.	2003 Jul	12885387
Comparison of the micro- and macro-vascular effects of glimepiride and gliclazide in metformin-treated patients with Type 2 diabetes: a double-blind, crossover study.	2003 Jun	12814458
Monocyte matrix metalloproteinase production in Type 2 diabetes and controls--a cross sectional study.	2003 Mar 10	12672267
A simple and sensitive HPLC method for determination of gliclazide in human serum.	2003 Mar 5	12554153
Spectrofluorimetric and spectrophotometric determination of gliclazide in pharmaceuticals by derivatization with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole.	2003 Mar-Apr	12723907
Effects of sulfonylureas on K(ATP) channel-dependent vasodilation.	2003 Mar-Apr	12623162
Effects of rosiglitazone maleate when added to a sulfonylurea regimen in patients with type 2 diabetes mellitus and mild to moderate renal impairment: a post hoc analysis.	2003 Nov	14693302
Reflex epilepsy and non-ketotic hyperglycemia.	2003 Sep	14684353

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.

Name

Type

Language

GLICLAZIDE

Official Name

English

SE 1702

Code

English

BENZENESULFONAMIDE, N-(((HEXAHYDROCYCLOPENTA(C)PYRROL-2(1H)-YL)AMINO)CARBONYL)-4-METHYL-

Systematic Name

English

SE-1702

Code

English

gliclazide [INN]

Common Name

English

GLICLAZIDE [MI]

Common Name

English

J3.151H

Code

English

Gliclazide [WHO-DD]

Common Name

English

S-1702

Code

English

NSC-758673

Code

English

GLICLAZIDE [EP MONOGRAPH]

Common Name

English

S-852

Code

English

DIAMICRON

Brand Name

English

GLICLAZIDE [JAN]

Common Name

English

1-(3-AZABICYCLO(3.3.0)OCT-3-YL)-3-(P-TOLYLSULFONYL)UREA

Common Name

English

GLIMICRON

Brand Name

English

GLICLAZIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97936