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
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+
DescriptionSources: http://www.medicines.org.uk/emc/medicine/31089Curator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23671878
Curator's Comment: Known to be CNS penetrant in rat. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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3.0 mM [Ki] | |||
Target ID: CHEMBL1944490 Sources: https://www.drugbank.ca/drugs/DB01120 |
50.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BILXONA Approved UseNon insulin-dependent diabetes (type 2) in adults when dietary measures, physical exercise and weight loss alone are not sufficient to control blood glucose. Launch Date2015 |
PubMed
Title | Date | PubMed |
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Gliclazide-induced acute hepatitis. | 2000 Jan |
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Comparison of acarbose and gliclazide as first-line agents in patients with type 2 diabetes. | 2001 |
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Gliclazide mainly affects insulin secretion in second phase of type 2 diabetes mellitus. | 2001 Jun |
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Gliclazide decreases vascular smooth muscle cell dysfunction induced by cell-mediated oxidized low-density lipoprotein. | 2001 Jun |
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[Toxicological analysis in the dawn of the third millenium]. | 2001 Sep-Oct |
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High-frequency insulin pulsatility and type 2 diabetes: from physiology and pathophysiology to clinical pharmacology. | 2002 Dec |
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Sulfonylurea stimulation of insulin secretion. | 2002 Dec |
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Does gliclazide stimulate first-phase, second-phase, or both phases of insulin release? | 2002 Feb |
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Adenosine triphosphate-sensitive potassium (K(ATP)) channel activity is coupled with insulin resistance in obesity and type 2 diabetes mellitus. | 2002 Feb |
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Oral hypoglycaemic agent failure. | 2002 Jul |
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Bioequivalence evaluation of two brands of gliclazide 80 mg tablets (Glyzide & Diamicron)--in healthy human volunteers. | 2002 Jul |
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Complete bioavailability and lack of food-effect on pharmacokinetics of gliclazide 30 mg modified release in healthy volunteers. | 2002 May |
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[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 |
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Addition of rosiglitazone to existing sulfonylurea treatment in chinese patients with type 2 diabetes and exposure to hepatitis B or C. | 2003 |
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Study of the solubilization of gliclazide by aqueous micellar solutions. | 2003 Apr |
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Severe relapsing sulphonylurea-induced hypoglycaemia: a diagnostic and therapeutic challenge. | 2003 Feb |
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The application of the convective diffusion model and the film equilibrium model to surfactant-facilitated dissolution of gliclazide. | 2003 Jul |
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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 |
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Monocyte matrix metalloproteinase production in Type 2 diabetes and controls--a cross sectional study. | 2003 Mar 10 |
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A simple and sensitive HPLC method for determination of gliclazide in human serum. | 2003 Mar 5 |
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Spectrofluorimetric and spectrophotometric determination of gliclazide in pharmaceuticals by derivatization with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole. | 2003 Mar-Apr |
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Effects of sulfonylureas on K(ATP) channel-dependent vasodilation. | 2003 Mar-Apr |
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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 |
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Reflex epilepsy and non-ketotic hyperglycemia. | 2003 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.medicines.org.uk/emc/medicine/31089
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11484080
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.
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NCI_THESAURUS |
C97936
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WHO-VATC |
QA10BB09
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WHO-ATC |
A10BB09
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244-260-5
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G4PX8C4HKV
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D005907
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SUB07921MIG
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667431
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1299
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GLICLAZIDE
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4816
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C87618
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DTXSID9023095
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21187-98-4
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100000090151
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31654
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DB01120
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3056
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m5744
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CHEMBL427216
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)