CHEBI:5441 - glyburide

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ChEBI Name glyburide
ChEBI ID CHEBI:5441
Definition An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H28ClN3O5S
Net Charge 0
Average Mass 494.00400
Monoisotopic Mass 493.144
InChI InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
InChIKey ZNNLBTZKUZBEKO-UHFFFAOYSA-N
SMILES COc1ccc(Cl)cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1
Roles Classification
Biological Role(s): EC 2.7.1.33 (pantothenate kinase) inhibitor
An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pantothenate kinase (EC 2.7.1.33).
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor
A EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of channel-conductance-controlling ATPase (EC 3.6.3.49, also known as cystic fibrosis conductance regulator, CFCR).
Application(s): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing glyburide (CHEBI:5441) has role anti-arrhythmia drug (CHEBI:38070)
glyburide (CHEBI:5441) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
glyburide (CHEBI:5441) has role EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor (CHEBI:131770)
glyburide (CHEBI:5441) has role hypoglycemic agent (CHEBI:35526)
glyburide (CHEBI:5441) is a N-sulfonylurea (CHEBI:76983)
glyburide (CHEBI:5441) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
5-chloro-N-(2-{4-[N-(N-cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide
INNs Sources
glibenclamida DrugBank
glibenclamide KEGG DRUG
glibenclamide WHO MedNet
glibenclamidum DrugBank
Synonyms Sources
1-((p-(2-(5-chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea ChemIDplus
1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea ChemIDplus
5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide ChemIDplus
Glyburide KEGG COMPOUND
Brand Names Sources
Diabeta KEGG DRUG
Glynase KEGG DRUG
Micronase KEGG DRUG
Database Links Databases
C07022 KEGG COMPOUND
D00336 KEGG DRUG
DB01016 DrugBank
Glibenclamide Wikipedia
LSM-2811 LINCS
NL6603398 Patent
NL6610580 Patent
US3454635 Patent
View more database links
Registry Numbers Types Sources
10238-21-8 CAS Registry Number ChemIDplus
2230085 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
16081479 PubMed citation Europe PMC
20797618 PubMed citation Europe PMC
Last Modified
19 April 2016