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

Molecular Formula	C15H21N3O3S
Molecular Weight	323.411
Charge	0
Count

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

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
Repaglinide: a review of its therapeutic use in type 2 diabetes mellitus.	2001	11577798
[Free radical scavenging activity of sulfonylureas: a clinical assessment of the effectiveness of gliclazide].	2001	11494442
ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms.	2001 Apr	11274860
Acute and short-term administration of a sulfonylurea (gliclazide) increases pulsatile insulin secretion in type 2 diabetes.	2001 Aug	11473038
Regulation of glucose transporter 1 expression by gliclazide in rat L6 myoblasts.	2001 Dec	11853362
Gliclazide and bedtime insulin are more efficient than insulin alone for type 2 diabetic patients with sulfonylurea secondary failure.	2001 Jan	11151028
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
Study rationale and design of ADVANCE: action in diabetes and vascular disease--preterax and diamicron MR controlled evaluation.	2001 Sep	11596665
A novel simple method for the investigation of drug binding to the K(ATP) channel sulfonylurea receptor.	2002 Aug 15	12202259
High-frequency insulin pulsatility and type 2 diabetes: from physiology and pathophysiology to clinical pharmacology.	2002 Dec	12703061
Gliclazide directly inhibits arginine-induced glucagon release.	2002 Dec	12475779
Interaction of the cytosolic domains of the Kir6.2 subunit of the K(ATP) channel is modulated by sulfonylureas.	2002 Dec	12475778
Trends in oral antihyperglycemic and insulin use in the Nova Scotia senior population (1993-1999).	2002 Fall	12422249
Does gliclazide stimulate first-phase, second-phase, or both phases of insulin release?	2002 Feb	11972296
Oral hypoglycaemic agent failure.	2002 Jul	12674170
Effect of pioglitazone on blood proinsulin levels in patients with type 2 diabetes mellitus.	2002 Jun	12201216
Screening, library-assisted identification and validated quantification of oral antidiabetics of the sulfonylurea-type in plasma by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry.	2002 Jun 15	12015271
Effective and selective prevention of retinal leukostasis in streptozotocin-induced diabetic rats using gliclazide.	2002 May	12107755
Eudragit NE30D based metformin/gliclazide extended release tablets: formulation, characterisation and in vitro release studies.	2002 Nov	12419917
Population PKPD modelling of the long-term hypoglycaemic effect of gliclazide given as a once-a-day modified release (MR) formulation.	2003 Feb	12580986
The application of the convective diffusion model and the film equilibrium model to surfactant-facilitated dissolution of gliclazide.	2003 Jul	12885387
Functional involvement of sulphonylurea receptor (SUR) type 1 and 2B in the activity of pig urethral ATP-sensitive K+ channels.	2003 Jun	12788825
Monocyte adhesion in diabetic angiopathy: effects of free-radical scavenging.	2003 Mar-Apr	12623165
[Medication of the month. Gliclazide modified release (Uni Diamicron)].	2003 Oct	14677526

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:15:33 GMT 2023` Edited by `admin` on `Fri Dec 15 19:15:33 GMT 2023`
Record UNII	G4PX8C4HKV
Record Status	`Validated (UNII)`
Record Version

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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