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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

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About This Item

Empirical Formula (Hill Notation):
C24H27NO5S
CAS Number:
97322-87-7
Molecular Weight:
441.54
MDL number:
MFCD00878416
UNSPSC Code:
12352200
PubChem Substance ID:
24724629
NACRES:
NA.77

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: 20 mg/mL

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)

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.

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
The Practice of Medicinal Chemistry (2015)
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
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