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Details

Stereochemistry ACHIRAL
Molecular Formula C15H21N3O3S
Molecular Weight 323.4122
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLICLAZIDE

SMILES

Cc1ccc(cc1)S(=O)(=O)NC(=NN2C[C@]3([H])CCC[C@]3([H])C2)O

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 323.4122
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
Gliclazide-induced acute hepatitis.
2000 Jan
Repaglinide: a review of its therapeutic use in type 2 diabetes mellitus.
2001
[Free radical scavenging activity of sulfonylureas: a clinical assessment of the effectiveness of gliclazide].
2001
Comparison of the effects of three sulfonylureas on in vivo insulin action.
2001
24-hour glycemic profile in type 2 diabetic patients treated with gliclazide modified release once daily.
2001 Apr
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.
2001 Feb
Gliclazide and bedtime insulin are more efficient than insulin alone for type 2 diabetic patients with sulfonylurea secondary failure.
2001 Jan
[Effects of gliclazide on blood rheology of diabetes Wistar rat].
2001 Jun
Gliclazide decreases vascular smooth muscle cell dysfunction induced by cell-mediated oxidized low-density lipoprotein.
2001 Jun
Characteristics of pancreatic beta-cell secretion in Type 2 diabetic patients treated with gliclazide and glibenclamide.
2001 May
Prescribing patterns and therapeutic implications for diabetic hypertension in Bahrain.
2001 Nov
[Recurrent toxic severe hypoglycemias].
2001 Nov-Dec
Possible interaction between gliclazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia.
2001 Oct
Gliclazide modified release.
2002
Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs.
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
Hypoglycaemic activity of Alpinia galanga rhizome and its extracts in rabbits.
2002 Dec
Interaction of the cytosolic domains of the Kir6.2 subunit of the K(ATP) channel is modulated by sulfonylureas.
2002 Dec
New trends in the development of oral antidiabetic drugs.
2002 Jan
Antiaggregatory activity of hypoglycaemic sulphonylureas.
2002 Jul
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
Acute gliclazide administration enhances glucose and ketone body utilization in the perfused hind limb of normal and streptozotocin-diabetic rats.
2002 Jun 28
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
Complete bioavailability and lack of food-effect on pharmacokinetics of gliclazide 30 mg modified release in healthy volunteers.
2002 May
Effect of gliclazide on islet transplants.
2002 Nov
Gliclazide improves anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes.
2002 Sep
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
Severe relapsing sulphonylurea-induced hypoglycaemia: a diagnostic and therapeutic challenge.
2003 Feb
Effects of inhibition of ATP-sensitive potassium channels on metabolic vasodilation in the human forearm.
2003 Jan
The application of the convective diffusion model and the film equilibrium model to surfactant-facilitated dissolution of gliclazide.
2003 Jul
Bioequivalence study of generic gliclazide and Diamicron formulations in healthy Thai male volunteers.
2003 Jul
Sulfonylureas and cardiovascular effects: from experimental data to clinical use. Available data in humans and clinical applications.
2003 Jun
Diabetes and vascular disease: a new international trial.
2003 Jun
Gliclazide protects pancreatic beta-cells from damage by hydrogen peroxide.
2003 Mar 28
Differential selectivity of insulin secretagogues: mechanisms, clinical implications, and drug interactions.
2003 Mar-Apr
Effects of sulfonylureas on K(ATP) channel-dependent vasodilation.
2003 Mar-Apr
Urinary PC-1 and N-acetyl-beta-D-glucosaminidase activity in patients with type 2 diabetes treated with metformin, gliclazide or glibenclamide.
2003 May
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
[Medication of the month. Gliclazide modified release (Uni Diamicron)].
2003 Oct
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 Fri Jun 25 21:12:26 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:26 UTC 2021
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
GLICLAZIDE [WHO-DD]
Common Name English
J3.151H
Code 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 Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
WHO-VATC QA10BB09
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
WHO-ATC A10BB09
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
244-260-5
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
FDA UNII
G4PX8C4HKV
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
MESH
D005907
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
EVMPD
SUB07921MIG
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
PUBCHEM
667431
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
DRUG CENTRAL
1299
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
WIKIPEDIA
GLICLAZIDE
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
RXCUI
4816
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C87618
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
EPA CompTox
21187-98-4
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
CAS
21187-98-4
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
DRUG BANK
DB01120
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
INN
3056
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
MERCK INDEX
M5744
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL427216
Created by admin on Fri Jun 25 21:12:26 UTC 2021 , Edited by admin on Fri Jun 25 21:12:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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ACTIVE MOIETY