CHEBI:31654 - gliclazide

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ChEBI Name gliclazide
ChEBI ID CHEBI:31654
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB0259026, eMolecules:35875953, eMolecules:12800964, ZINC000031155604
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Gliclazide, sold under the brand name Diamicron among others, is a sulfonylurea type of anti-diabetic medication, used to treat type 2 diabetes. It is used when dietary changes, exercise, and weight loss are not enough. It is taken by mouth. Side effect may include low blood sugar, vomiting, abdominal pain, rash, and liver problems. Use by those with significant kidney problems or liver problems or who are pregnant is not recommended. Gliclazide is in the sulfonylurea family of medications. It works mostly by increasing the release of insulin. Gliclazide was patented in 1966 and approved for medical use in 1972. It is on the World Health Organization's List of Essential Medicines. It is not available for sale in the United States.
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Formula C15H21N3O3S
Net Charge 0
Average Mass 323.41100
Monoisotopic Mass 323.13036
InChI 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)
InChIKey BOVGTQGAOIONJV-UHFFFAOYSA-N
SMILES Cc1ccc(cc1)S(=O)(=O)NC(=O)NN1CC2CCCC2C1
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): insulin secretagogue
A secretagogue that causes the secretion of insulin.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing gliclazide (CHEBI:31654) has role hypoglycemic agent (CHEBI:35526)
gliclazide (CHEBI:31654) has role insulin secretagogue (CHEBI:90415)
gliclazide (CHEBI:31654) has role radical scavenger (CHEBI:48578)
gliclazide (CHEBI:31654) is a N-sulfonylurea (CHEBI:76983)
IUPAC Name
N-(hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl)-4-methylbenzenesulfonamide
Synonyms Sources
1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea ChemIDplus
1-(hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea ChemIDplus
Gliclazide ChemIDplus
Glimicron ChemIDplus
Manual Xrefs Databases
1299 DrugCentral
D01599 KEGG DRUG
DB01120 DrugBank
Gliclazide Wikipedia
HMDB0015252 HMDB
LSM-5096 LINCS
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Registry Numbers Types Sources
1657836 Reaxys Registry Number Reaxys
21187-98-4 CAS Registry Number ChemIDplus
21187-98-4 CAS Registry Number KEGG DRUG
Citations Types Sources
10048179 PubMed citation Europe PMC
14871415 PubMed citation Europe PMC
16631804 PubMed citation Europe PMC
22118706 PubMed citation Europe PMC
22183301 PubMed citation Europe PMC
22411174 PubMed citation Europe PMC
22732450 PubMed citation Europe PMC
9226746 PubMed citation Europe PMC
Last Modified
22 February 2017