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T2573 Sigma-Aldrich

Troglitazone

≥98% (HPLC)

Synonym: (±)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione, CS-045

  • CAS Number 97322-87-7

  • Empirical Formula (Hill Notation) C24H27NO5S

  • Molecular Weight 441.54

  •  MDL number MFCD00878416

  •  PubChem Substance ID 24724629

  •  NACRES NA.77

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Properties

Related Categories Antitumor Agents, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Research,
Quality Level   200
assay   ≥98% (HPLC)
form   powder
color   white to off-white
solubility   DMSO: 20 mg/mL
originator   Pfizer
SMILES string   Cc1c(C)c2OC(C)(CCc2c(C)c1O)COc3ccc(CC4SC(=O)NC4=O)cc3
InChI   1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
InChI key   GXPHKUHSUJUWKP-UHFFFAOYSA-N
Gene Information   human ... PPARA(5465), PPARG(5468)

Description

General description

Troglitazone is used to treat type 2 diabetes. It is associated with liver injury. Troglitazone functions as an inducer of cytochrome3A.

Application

Troglitazone has been used as a reagent in adipocyte differentiation medium.

Packaging

5 mg in glass bottle

Biochem/physiol Actions

PPARγ agonist; anti-diabetic thiazolidinedione (TZD) with anti-inflammatory and anti-tumor activity; induces apoptosis via a p53 pathway.

Features and Benefits

This compound is featured on the Nuclear Receptors (PPARs) and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Studies using troglitazone have reported that it can increase AMP-activated protein kinase (pAMPK) and phosphorylated acetyl-CoA carboxylase in isolated rat extensor digitorum longus muscles1. Furthermore, analysis of troglitazone-mediated autophagy is reported to correlate with the stimulation of AMPK α2.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
RTECS 
XJ5813130
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Insulin Signaling and Energy Homeostasis

Glucose metabolism is regulated by the opposing actions of insulin and glucagon. Insulin is released from pancreatic ß cells in response to high blood glucose levels and regulates glucose metabolism ...
Linda Stephenson, Ph.D.
Biofiles v6 n4, 2011
Keywords: Apoptosis, Biological processes, Carboxylations, Catalog, Diabetes, Gene expression, Gluconeogenesis, Glycolysis, Hormones, Metabolism, Metabolites, Transcription, Transduction, Type

Peer-Reviewed Papers
15

References

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