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R2408

Sigma-Aldrich

Rosiglitazone

≥98% (HPLC)

Synonyme(s) :

Rosiglitazone, 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

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About This Item

Formule linéaire :
C18H19N3O3S
Numéro CAS:
122320-73-4
Poids moléculaire :
357.43
Numéro MDL:
MFCD00871760
Code UNSPSC :
12352200
ID de substance PubChem :
329824017
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: ≥10 mg/mL

Auteur

GlaxoSmithKline

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

YASAKCUCGLMORW-UHFFFAOYSA-N

Informations sur le gène

human ... PPARG(5468)

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Description générale

Rosiglitazone is a member of the thiazolidinedione family. It effectively lowers glucose levels by enhancing the response of target cells to insulin, without causing increased stimulation and release of insulin by the pancreatic beta cells. Rosiglitazone functions by activating the nuclear peroxisome proliferator-activated (PPAR) receptor gamma, which plays a key role in regulating adipogenesis, glucose metabolism, and genetic networks. It exhibits high potency as a thiazolidinedione, with a binding affinity for PPAR-gamma that is 30-fold higher than pioglitazone. Furthermore, it increases insulin-stimulated IRS-1/2 in skeletal muscle and adipose tissue, leading to the expression of the GLUT4 glucose transporter.

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

A novel role for Bcl2l13 in promoting beige adipocyte biogenesis
Ju L, et al.
Biochemical and Biophysical Research Communications, 506(3), 485-491 (2018)
Jérôme Carayol et al.
Nature communications, 8(1), 2084-2084 (2017-12-14)
Thousands of genetic variants have been associated with complex traits through genome-wide association studies. However, the functional variants or mechanistic consequences remain elusive. Intermediate traits such as gene expression or protein levels are good proxies of the metabolic state of
Rosiglitazone diminishes the high-glucose-induced modulation of 5-fluorouracil cytotoxicity in colorectal cancer cells
Lau MF, et al.
EXCLI Journal, 17, 186-186 (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
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
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