CHEBI:50122 - rosiglitazone

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ChEBI Name rosiglitazone
ChEBI ID CHEBI:50122
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H19N3O3S
Net Charge 0
Average Mass 357.42700
Monoisotopic Mass 357.11471
InChI InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)
InChIKey YASAKCUCGLMORW-UHFFFAOYSA-N
SMILES CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): insulin-sensitizing drug
An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
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.
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).
Application(s): insulin-sensitizing drug
An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rosiglitazone (CHEBI:50122) has role EC 6.2.1.3 (long-chain-fatty-acid—CoA ligase) inhibitor (CHEBI:83157)
rosiglitazone (CHEBI:50122) has role ferroptosis inhibitor (CHEBI:173084)
rosiglitazone (CHEBI:50122) has role insulin-sensitizing drug (CHEBI:50864)
rosiglitazone (CHEBI:50122) is a aminopyridine (CHEBI:38207)
rosiglitazone (CHEBI:50122) is a thiazolidinediones (CHEBI:50990)
Incoming rosiglitazone maleate (CHEBI:8892) has part rosiglitazone (CHEBI:50122)
(−)-rosiglitazone (CHEBI:50125) is a rosiglitazone (CHEBI:50122)
(+)-rosiglitazone (CHEBI:50123) is a rosiglitazone (CHEBI:50122)
IUPAC Name
5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
INNs Sources
rosiglitazona ChEBI
rosiglitazone ChemIDplus
rosiglitazonum ChEBI
Synonyms Sources
5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione ChemIDplus
BRL-49653 ChemIDplus
Manual Xrefs Databases
2405 DrugCentral
DB00412 DrugBank
EP306228 Patent
LSM-1949 LINCS
Rosiglitazone Wikipedia
US5002953 Patent
View more database links
Registry Numbers Types Sources
122320-73-4 CAS Registry Number ChemIDplus
7082202 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17259370 PubMed citation Europe PMC
30225267 PubMed citation Europe PMC
31936729 PubMed citation Europe PMC
32234642 PubMed citation Europe PMC
33650786 PubMed citation Europe PMC
33746608 PubMed citation Europe PMC
Last Modified
27 May 2021