R2408

Sigma-Aldrich

Rosiglitazone

≥98% (HPLC)

Synonym(s):
5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione, Rosiglitazone
Linear Formula:
C18H19N3O3S
CAS Number:
Molecular Weight:
357.43
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥10 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c3ccccn3

InChI

1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

InChI key

YASAKCUCGLMORW-UHFFFAOYSA-N

Gene Information

human ... PPARG(5468)

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Application

Rosiglitazone has been used:
  • as a medium constituent for adipocyte differentiation
  • in the cell proliferation assay in human colonic carcinoma cell lines
  • for Bcl-2-like protein 13 (Bcl2l13) expression in adipocytes
  • as a peroxisome proliferator-activated receptor gamma (PPARγ) ligand

Packaging

10, 50 mg in glass bottle

Biochem/physiol Actions

Rosiglitazone is a potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. It is antidiabetic, working as an insulin sensitizer by binding to the PPARγ receptors in fat cells and making the cells more responsive to insulin.

Features and Benefits

This compound is a featured product for ADME Tox and Gene Regulation research. Discover more featured ADME Tox and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the AMPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

A novel role for Bcl2l13 in promoting beige adipocyte biogenesis
Ju L, et al.
Biochemical and Biophysical Research Communications, 506(3), 485-491 (2018)
Siyu Xie et al.
Nutrients, 11(7) (2019-07-22)
Promoting white-to-beige adipocyte transition is a promising approach for obesity treatment. Although Liensinine (Lie), a kind of isoquinoline alkaloid, has been reported to affect white-to-beige adipocyte transition, its effects on inhibiting beige adipocytes recovering to white adipocytes and maintaining the...
Diego Caprioglio et al.
Planta medica, 85(11-12), 981-986 (2019-04-02)
A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semisynthetic monomethyl analogues of cannabigerol, cannabidiol, and cannabidivarin (1A: -3A: , respectively) made it possible to quantify these minor phytocannabinoids in about 40 different chemotypes...
María Isabel Cuartero et al.
Stroke, 44(12), 3498-3508 (2013-10-19)
Neutrophils have been traditionally recognized as major mediators of a deleterious inflammatory response in acute ischemic stroke, but their potential as a therapeutic target remains unexplored. Recent evidence indicates that neutrophils may acquire different phenotypes and contribute to resolution of...
CACUL1 reciprocally regulates SIRT1 and LSD1 to repress PPARgamma and inhibit adipogenesis
Jang MJ, et al.
Cell Death & Disease, 8(12), 3201-3201 (2017)
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