rosiglitazone (CHEBI:50122)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	rosiglitazone

ChEBI ID	CHEBI:50122

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Wikipedia	License

Read full article at Wikipedia

Formula

C18H19N3O3S

Net Charge

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).

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) rosiglitazone (CHEBI:50122) is conjugate acid of rosiglitazone(1−) (CHEBI:188074)

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) rosiglitazone(1−) (CHEBI:188074) is conjugate base of rosiglitazone (CHEBI:50122)

IUPAC Name

5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione

Synonyms	Sources
5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione	ChemIDplus
BRL-49653	ChemIDplus

Last Modified

27 May 2021