R2408

Rosiglitazone

≥98% (HPLC)

• Synonym(s): Rosiglitazone, 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
• Linear Formula: C₁₈H₁₉N₃O₃S
• CAS Number: 122320-73-4
• Molecular Weight: 357.43
• MDL number: MFCD00871760
• UNSPSC Code: 12352200
• PubChem Substance ID: 329824017
• NACRES: NA.77

Properties

• Quality Level: 100
• 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)

Description

General description

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

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.

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable