557366-M

Rosiglitazone

A thiazolidinedione compound that acts as an anti-diabetic agent and serves as a potent and selective agonist of peroxisome proliferator-activated receptor-γ (PPARγ) (Kd ~40 nM) in fat cells.

• Synonym(s): Rosiglitazone, AMPK Signaling Activator X, 5-[4-(2-[methyl(pyridin-2-yl)amino]ethoxy)benzyl]thiazolidine-2,4-dione, BRL49653, Avandia, PPAR Agonist X, PPARγ Agonist IX
• CAS Number: 155141-29-0
• MDL number: MFCD03427306
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥99% (HPLC)
• Form: powder
• Storage condition: OK to freeze, protect from light

Properties

• Quality Segment: 100
• assay: ≥99% (HPLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 100 mg/mL
• storage temp.: −20°C
• SMILES string: S1C(C(=O)[N+H2]C1=O)Cc2ccc(cc2)OCC[N+H](C)c3ncccc3.[O-]C(=O)\C=C/C(=O)[O-]
• InChI: 1S/C18H19N3O3S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChI key: SUFUKZSWUHZXAV-BTJKTKAUSA-N

Description

General description

A thiazolidinedione compound that acts as an anti-diabetic agent and serves as a potent and selective agonist of peroxisome proliferator-activated receptor-g (PPARg) (K_d ~40 nM) in fat cells. Shown to reduce fatty acid uptake and ameliorate lipid metabolism and insulin resistance in animal models of type II diabetes. Reported to activate both a1- and a2-containing AMPK complexes. Unlike troglitazone, it does not induce the activity of P4503A4. Significantly improves the differentiation of C3H10T1/2 stem cells into adipocytes. Shown to block estrogen synthesis by interfering with androgen binding to aromatase, but without affecting aromatase mRNA or protein expression.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Araki, T., et al. 2011. PPAR Res.2011, 926438.
Sozio, M. S., et al. 2011. Am. J. Physiol. Gastrointest. Liver Physiol. 301, G739.
Gerstein, H., et al. 2006. Drug 368, 9541.
Mohanty, P., 2004. Journ. Clin. Endocrin. & Metab. 89(6), 2728-2735.
Fryer, L., et al. 2002. J Biol Chem 277, 25226.
Goldberg, R., et al. 1999. Drug. 57, 921.
Young, P., et al. 1998. Journ. Pharm. Exp. Ther. 284, 751.
Willson, T., et al. 1996. J. Med. Chem.39, 665; Lehmann, J., et al., 1995. JBC270, 12953.
Cantello, B., et al., 1994. Bioorg. Med. Chem. Lett. 4, 1181.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• WGK: WGK 3
• Pictograms: GHS07
• Signal Word: Warning
• Hazard Codes: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral