CHEBI:8228 - pioglitazone

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ChEBI Name pioglitazone
ChEBI ID CHEBI:8228
Definition A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H20N2O3S
Net Charge 0
Average Mass 356.43978
Monoisotopic Mass 356.119
InChI InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
InChIKey HYAFETHFCAUJAY-UHFFFAOYSA-N
SMILES CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1
Roles Classification
Biological Role(s): insulin-sensitizing drug
An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
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).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): insulin-sensitizing drug
An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
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ChEBI Ontology
Outgoing pioglitazone (CHEBI:8228) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
pioglitazone (CHEBI:8228) has role insulin-sensitizing drug (CHEBI:50864)
pioglitazone (CHEBI:8228) has role xenobiotic (CHEBI:35703)
pioglitazone (CHEBI:8228) is a aromatic ether (CHEBI:35618)
pioglitazone (CHEBI:8228) is a pyridines (CHEBI:26421)
pioglitazone (CHEBI:8228) is a thiazolidenediones (CHEBI:50990)
Incoming hydroxypioglitazone (CHEBI:82937) has functional parent pioglitazone (CHEBI:8228)
IUPAC Name
5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione
INNs Sources
pioglitazona ChemIDplus
pioglitazone ChemIDplus
pioglitazonum ChemIDplus
Synonyms Sources
(±)-5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione ChemIDplus
Pioglitazone KEGG COMPOUND
Database Links Databases
2179 DrugCentral
C07675 KEGG COMPOUND
D08378 KEGG DRUG
DB01132 DrugBank
EP193256 Patent
HMDB0015264 HMDB
LSM-1592 LINCS
Pioglitazone Wikipedia
US4687777 Patent
View more database links
Registry Numbers Types Sources
111025-46-8 CAS Registry Number ChemIDplus
3595485 Beilstein Registry Number Beilstein
3595485 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
20797618 PubMed citation Europe PMC
Last Modified
22 February 2017