troglitazone (BioCAD00000186492)
Metabolite Card
Formula: C24H27NO5S (441.161)
SMILES: CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O
Synonyms [en]
Troglitazone; Prelay; Rezulin; troglitazona; troglitazonum; Romglizone
Last reviewed on 2024-06-28.
Cite this Page
troglitazone. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000186492). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Troglitazone is a member of chromanes and a thiazolidinone. It has a role as a hypoglycemic agent, an antioxidant, a vasodilator agent, an anticonvulsant, an anticoagulant, a platelet aggregation inhibitor, an antineoplastic agent, an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor and a ferroptosis inhibitor. Troglitazone was withdrawn in 2000 due to risk of hepatotoxicity. It was superseded by [pioglitazone] and [rosiglitazone]. Troglitazone was the first thiazolidinedione approved for use in the United States and was licensed for use in type 2 diabetes in 1997, but withdrawn 3 years later because of the frequency of liver injury including acute liver failure associated with its use. Troglitazone is an orally-active thiazolidinedione with antidiabetic and hepatotoxic properties and potential antineoplastic activity. Troglitazone activates peroxisome proliferator-activated receptor gamma (PPAR-gamma), a ligand-activated transcription factor, thereby inducing cell differentiation and inhibiting cell growth and angiogenesis. This agent also modulates the transcription of insulin-responsive genes, inhibits macrophage and monocyte activation, and stimulates adipocyte differentiation. (NCI04) Troglitazone was withdrawn in 2000 due to risk of hepatotoxicity. It was superseded by pioglitazone and rosiglitazone. A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.
DBLinks
- CAS Registry Number: 97322-87-7
- PubChem CID: 5591
- ChEBI: 9753
- HMDB: HMDB0259292
- LipidMaps:
- KEGG: D00395
- BioCyc: CPD-11439
- NCBI MeSH: Troglitazone
- Wikipedia: Troglitazone
Other DBLinks
- CAS Registry Number: 97322-87-7
- PubChem: 5591
- PubChem: 6518172
- ChEBI: ChEBI:9753
- HMDB: HMDB0259292
- KEGG: C07181
- KEGG: D00395
- NCBI MeSH: Troglitazone
- Wikipedia: Troglitazone
- DrugBank: DB00197
- RefMet: RM0187657
- MoNA: LU070104
- MoNA: LU070105
- MoNA: LU070151
- MoNA: LU070152
- MoNA: LU070153
- MoNA: LU070154
- MoNA: LU070155
- MoNA: LU070156
- Metlin: METLIN_2970
- Coconut NaturalProduct: CNP0599572.0
Class / Ontology
- WishartLab ClassyFire: [1-benzopyrans] 1-benzopyrans
- RefMet: [1-benzopyrans] 1-benzopyrans
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_PWY-6261 | thyroid hormone metabolism II (via conjugation and/or degradation) |
| WikiPathways:WP2289 | Drug induction of bile acid pathway |
| WikiPathways:WP3253 | Drug induction of bile acid pathway |