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.
Supplier Information ChemicalBook:CB0506416, ChemicalBook:CB9667842, ChemicalBook:CB8117582, eMolecules:492467, ZINC000001700075
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Formula C19H20N2O3S
Net Charge 0
Average Mass 356.43978
Monoisotopic Mass 356.11946
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.
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor
An EC 6.2.1.* (acid-thiol ligase) inhibitor that interferes with the action of a long-chain-fatty-acidCoA ligase (EC 6.2.1.3).
ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
PPARgamma agonist
A PPAR modulator which activates the peroxisome proliferator-activated receptor-gamma.
Application(s): insulin-sensitizing drug
An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
hypoglycemic agent
A drug which lowers the blood glucose level.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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ChEBI Ontology
Outgoing pioglitazone (CHEBI:8228) has role antidepressant (CHEBI:35469)
pioglitazone (CHEBI:8228) has role cardioprotective agent (CHEBI:77307)
pioglitazone (CHEBI:8228) has role EC 2.7.1.33 (pantothenate kinase) inhibitor (CHEBI:77194)
pioglitazone (CHEBI:8228) has role EC 6.2.1.3 (long-chain-fatty-acid—CoA ligase) inhibitor (CHEBI:83157)
pioglitazone (CHEBI:8228) has role ferroptosis inhibitor (CHEBI:173084)
pioglitazone (CHEBI:8228) has role geroprotector (CHEBI:176497)
pioglitazone (CHEBI:8228) has role hypoglycemic agent (CHEBI:35526)
pioglitazone (CHEBI:8228) has role insulin-sensitizing drug (CHEBI:50864)
pioglitazone (CHEBI:8228) has role PPARγ agonist (CHEBI:71554)
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 thiazolidinediones (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
Manual Xrefs Databases
2179 DrugCentral
4663 ChemSpider
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 Reaxys Registry Number Reaxys
Citations
Last Modified
28 October 2021