T2573

Sigma-Aldrich

Troglitazone

≥98% (HPLC)

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

human ... PPARA(5465), PPARG(5468)

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.

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Phil June Park et al.
International journal of molecular sciences, 20(8) (2019-04-18)
Adiponectin (APN), released mainly from adipose tissue, is a well-known homeostatic factor for regulating glucose levels, lipid metabolism, and insulin sensitivity. A recent study showed that human hair follicles express APN receptors and the presence of APN-mediated hair growth signaling...
Registered report: IDH mutation impairs histone demethylation and results in a block to cell differentiation
Richarson AD, et al.
eLife, 5, e10860-e10860 (2016)
Troglitazone hepatotoxicity: are we getting closer to understanding idiosyncratic liver injury?
Jaeschke H
Toxicological Sciences, 97(1), 1-3 (2007)
Yuko Okamatsu-Ogura et al.
Scientific reports, 7(1), 6648-6648 (2017-07-29)
We previously reported brown adipocytes can proliferate even after differentiation. To test the involvement of mature adipocyte proliferation in cell number control in fat tissue, we generated transgenic (Tg) mice over-expressing cell-cycle inhibitory protein p27 specifically in adipocytes, using the...
Reprogramming of Human Cord Blood CD34+ Cells into Induced MSCs
Hematopoietic Differentiation of Human Pluripotent Stem Cells, 91-101 (2015)
Articles
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 through its actions on muscle, liver, and adipose tissue.
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