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T2573

Sigma-Aldrich

Troglitazone

≥98% (HPLC)

Synonym(s):
(±)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione, CS-045
Empirical Formula (Hill Notation):
C24H27NO5S
CAS Number:
Molecular Weight:
441.54
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Related Categories

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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