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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 of GLICLAZIDE

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
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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 mM [Ki]
50.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.42888324E12
PubMed

PubMed

TitleDatePubMed
[Antioxidant and anti-AGE therapeutics: evaluation and perspectives].
2001
Glibenclamide vs gliclazide in reducing oxidative stress in patients of noninsulin dependent diabetes mellitus--a double blind randomized study.
2001 Aug
Regulation of glucose transporter 1 expression by gliclazide in rat L6 myoblasts.
2001 Dec
ATP-Sensitive potassium channels modulate glucose transport in cultured human skeletal muscle cells.
2001 Jun
Increments in insulin sensitivity during intensive treatment are closely correlated with decrements in glucocorticoid receptor mRNA in skeletal muscle from patients with Type II diabetes.
2001 Nov
Determination of gliclazide in pharmaceutical preparations by capillary gas chromatography with cool on-column injection and elimination of the matrix effect.
2001 Nov-Dec
[Recurrent toxic severe hypoglycemias].
2001 Nov-Dec
Possible interaction between gliclazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia.
2001 Oct
Liver failure after long-term nucleoside antiretroviral therapy.
2001 Sep 1
Gliclazide modified release.
2002
A novel simple method for the investigation of drug binding to the K(ATP) channel sulfonylurea receptor.
2002 Aug 15
[Molecular mechanisms of insulin secretion].
2002 Dec
Sulfonylurea stimulation of insulin secretion.
2002 Dec
Gliclazide increases insulin receptor tyrosine phosphorylation but not p38 phosphorylation in insulin-resistant skeletal muscle cells.
2002 Dec
Trends in oral antihyperglycemic and insulin use in the Nova Scotia senior population (1993-1999).
2002 Fall
Adenosine triphosphate-sensitive potassium (K(ATP)) channel activity is coupled with insulin resistance in obesity and type 2 diabetes mellitus.
2002 Feb
New trends in the development of oral antidiabetic drugs.
2002 Jan
Antiaggregatory activity of hypoglycaemic sulphonylureas.
2002 Jul
Effect of ethanolic extract of Embelia ribes on dyslipidemia in diabetic rats.
2002 Jul-Sep
Effect of pioglitazone on blood proinsulin levels in patients with type 2 diabetes mellitus.
2002 Jun
Studies on solubility and hypoglycemic activity of gliclazide beta-cyclodextrin-hydroxypropylmethylcellulose complexes.
2002 Mar
Effective and selective prevention of retinal leukostasis in streptozotocin-induced diabetic rats using gliclazide.
2002 May
Gliclazide-induced acute hepatitis with hypersensitivity features.
2002 May
Participation of high glucose concentrations in neutrophil adhesion and surface expression of adhesion molecules on cultured human endothelial cells: effect of antidiabetic medicines.
2002 May-Jun
Effect of gliclazide on islet transplants.
2002 Nov
Eudragit NE30D based metformin/gliclazide extended release tablets: formulation, characterisation and in vitro release studies.
2002 Nov
Gateways to Clinical Trials.
2002 Sep
Gliclazide improves anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes.
2002 Sep
[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
Study of the solubilization of gliclazide by aqueous micellar solutions.
2003 Apr
Gliclazide modified release: A critical review of pharmacodynamic, metabolic, and vasoprotective effects.
2003 Aug
Benefits of gliclazide in the atherosclerotic process: decrease in monocyte adhesion to endothelial cells.
2003 Aug
Population PKPD modelling of the long-term hypoglycaemic effect of gliclazide given as a once-a-day modified release (MR) formulation.
2003 Feb
Bioequivalence study of generic gliclazide and Diamicron formulations in healthy Thai male volunteers.
2003 Jul
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
Monocyte matrix metalloproteinase production in Type 2 diabetes and controls--a cross sectional study.
2003 Mar 10
Gliclazide protects pancreatic beta-cells from damage by hydrogen peroxide.
2003 Mar 28
A simple and sensitive HPLC method for determination of gliclazide in human serum.
2003 Mar 5
Monocyte adhesion in diabetic angiopathy: effects of free-radical scavenging.
2003 Mar-Apr
Effects of sulfonylureas on K(ATP) channel-dependent vasodilation.
2003 Mar-Apr
Upregulation of cyclooxygenase-2 is accompanied by increased expression of nuclear factor-kappa B and I kappa B kinase-alpha in human colorectal cancer epithelial cells.
2003 May 19
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
Comparison of repaglinide vs. gliclazide in combination with bedtime NPH insulin in patients with Type 2 diabetes inadequately controlled with oral hypoglycaemic agents.
2003 Nov
[Medication of the month. Gliclazide modified release (Uni Diamicron)].
2003 Oct
Risk of hypoglycaemia with oral antidiabetic agents in patients with Type 2 diabetes.
2003 Oct
Monotherapy of type 2 diabetes with once-daily gliclazide modified release in primary care.
2003 Oct
Effect of rifampin on the pharmacokinetics and pharmacodynamics of gliclazide.
2003 Oct
Genetic cause of hyperglycaemia and response to treatment in diabetes.
2003 Oct 18
Reflex epilepsy and non-ketotic hyperglycemia.
2003 Sep
Phosphatidylinositol 3-kinase activation is required for sulfonylurea stimulation of glucose transport in rat skeletal muscle.
2004 Feb
Patents

Sample Use Guides

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
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 Thu Jul 06 02:23:06 UTC 2023
Edited
by admin
on Thu Jul 06 02:23:06 UTC 2023
Record UNII
G4PX8C4HKV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLICLAZIDE
EP   INN   JAN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
WHO-VATC QA10BB09
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
WHO-ATC A10BB09
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
244-260-5
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
FDA UNII
G4PX8C4HKV
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
MESH
D005907
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
EVMPD
SUB07921MIG
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
PUBCHEM
667431
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
DRUG CENTRAL
1299
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
WIKIPEDIA
GLICLAZIDE
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
RXCUI
4816
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C87618
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023095
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
CAS
21187-98-4
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
SMS_ID
100000090151
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
NSC
758673
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
CHEBI
31654
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
DRUG BANK
DB01120
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
INN
3056
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
MERCK INDEX
M5744
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL427216
Created by admin on Thu Jul 06 02:23:06 UTC 2023 , Edited by admin on Thu Jul 06 02:23:06 UTC 2023
PRIMARY
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