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
[Antioxidant and anti-AGE therapeutics: evaluation and perspectives].	2001	11938556
[Free radical scavenging activity of sulfonylureas: a clinical assessment of the effectiveness of gliclazide].	2001	11494442
Comparison of the effects of three sulfonylureas on in vivo insulin action.	2001	11455676
Sulfonylurea treatment of type 2 diabetic patients does not reduce the vasodilator response to ischemia.	2001 Apr	11315840
Acute and short-term administration of a sulfonylurea (gliclazide) increases pulsatile insulin secretion in type 2 diabetes.	2001 Aug	11473038
Gliclazide mainly affects insulin secretion in second phase of type 2 diabetes mellitus.	2001 Jun	11456286
Study rationale and design of ADVANCE: action in diabetes and vascular disease--preterax and diamicron MR controlled evaluation.	2001 Sep	11596665
Liver failure after long-term nucleoside antiretroviral therapy.	2001 Sep 1	11556343
Gliclazide modified release.	2002	12076188
Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs.	2002	12016548
Combination therapy of alpha-glucosidase inhibitor and a sulfonylurea compound prolongs the duration of good glycemic control.	2002 Dec	12489066
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
Sulfonylurea stimulation of insulin secretion.	2002 Dec	12475777
Antiaggregatory activity of hypoglycaemic sulphonylureas.	2002 Jul	12136403
Bioequivalence evaluation of two brands of gliclazide 80 mg tablets (Glyzide & Diamicron)--in healthy human volunteers.	2002 Jul	12116051
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
Studies on solubility and hypoglycemic activity of gliclazide beta-cyclodextrin-hydroxypropylmethylcellulose complexes.	2002 Mar	11933849
Effective and selective prevention of retinal leukostasis in streptozotocin-induced diabetic rats using gliclazide.	2002 May	12107755
Gateways to Clinical Trials.	2002 Sep	12428432
Diabetes mellitus and weight control: differences of respiratory quotient in type 2 diabetic obese subjects receiving sulfonylureas and non-diabetic obese controls.	2003 Feb	12591550
Pharmacokinetic and pharmacodynamic characterization of gliclazide in healthy volunteers.	2003 Jul	12934650
Diabetes and vascular disease: a new international trial.	2003 Jun	12878575
Functional involvement of sulphonylurea receptor (SUR) type 1 and 2B in the activity of pig urethral ATP-sensitive K+ channels.	2003 Jun	12788825
Monocyte matrix metalloproteinase production in Type 2 diabetes and controls--a cross sectional study.	2003 Mar 10	12672267
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
Effect of rifampin on the pharmacokinetics and pharmacodynamics of gliclazide.	2003 Oct	14534520
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.

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