CHEBI:5384 - glipizide

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ChEBI Name glipizide
ChEBI ID CHEBI:5384
Definition An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H27N5O4S
Net Charge 0
Average Mass 445.53500
Monoisotopic Mass 445.178
InChI InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
InChIKey ZJJXGWJIGJFDTL-UHFFFAOYSA-N
SMILES Cc1cnc(cn1)C(=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).
insulin secretagogue
A secretagogue that causes the secretion of insulin.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing glipizide (CHEBI:5384) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
glipizide (CHEBI:5384) has role hypoglycemic agent (CHEBI:35526)
glipizide (CHEBI:5384) has role insulin secretagogue (CHEBI:90415)
glipizide (CHEBI:5384) is a N-sulfonylurea (CHEBI:76983)
glipizide (CHEBI:5384) is a aromatic amide (CHEBI:62733)
glipizide (CHEBI:5384) is a monocarboxylic acid amide (CHEBI:29347)
glipizide (CHEBI:5384) is a pyrazines (CHEBI:38314)
IUPAC Name
N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-5-methylpyrazine-2-carboxamide
INNs Sources
glipizida WHO MedNet
glipizide WHO MedNet
glipizide WHO MedNet
glipizidum WHO MedNet
Synonyms Sources
1-cyclohexyl-3-({p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyl}sulfonyl)urea ChemIDplus
CP 28,720 ChemIDplus
CP 28720 ChemIDplus
CP-28,720 ChemIDplus
K 4024 ChemIDplus
N-{4-[β-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulphonyl}-N'-cyclohexylurea ChemIDplus
Brand Names Sources
Aldiab DrugBank
Digrin ChemIDplus
Dipazide ChemIDplus
Glibenese ChemIDplus
Glibetin ChemIDplus
Glican ChemIDplus
Glidiab ChemIDplus
Glipid ChemIDplus
Gluco-Rite ChemIDplus
Glucolip ChemIDplus
Glucotrol KEGG DRUG
Glucozide ChemIDplus
Glupitel ChemIDplus
Glupizide ChemIDplus
Glyde ChemIDplus
Glydiazinamide ChemIDplus
Melizide ChemIDplus
Mindiab ChemIDplus
Minidab ChemIDplus
Minidiab ChemIDplus
Minodiab ChemIDplus
Napizide ChemIDplus
Ozidia ChemIDplus
Sucrazide ChemIDplus
Manual Xrefs Databases
1301 DrugCentral
D00335 KEGG DRUG
DB01067 DrugBank
DE2012138 Patent
Glipizide Wikipedia
HMDB0015200 HMDB
LSM-2251 LINCS
US3669966 Patent
View more database links
Registry Numbers Types Sources
29094-61-9 CAS Registry Number ChemIDplus
903495 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11147395 PubMed citation Europe PMC
20797618 PubMed citation Europe PMC
23230096 PubMed citation Europe PMC
24418334 PubMed citation Europe PMC
24444583 PubMed citation Europe PMC
2665487 PubMed citation Europe PMC
3143256 PubMed citation Europe PMC
389600 PubMed citation Europe PMC
3923454 PubMed citation Europe PMC
7660535 PubMed citation Europe PMC
Last Modified
22 February 2017