Skip to Content
Merck
CN

Key Documents

View All Documentation

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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) (Kd ~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)

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk

WGK 3

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Global Trade Item Number

SKUGTIN
557366-10MG-M04055977268027