RosiglitazoneA potent and selective PPARγ agonist

Rosiglitazone (CAS 122320-73-4)

Rosiglitazone | CAS 122320-73-4 is rated 5.0 out of 5 by 1.
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Synonym: 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Application: A potent and selective PPARγ agonist
CAS Number: 122320-73-4
Purity: ≥98%
Molecular Weight: 357.43
Molecular Formula: C18H19N3O3S
* Refer to Certificate of Analysis for lot specific data (including water content).
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Rosiglitazone is a potent, selective PPARγ (Peroxisome proliferator-activated receptor) agonist (Kd= 43 nM) which exhibits anti-diabetic and hepatotoxic effects. PPARγ belongs to a group of nuclear receptor proteins that are essential to the regulation of cellular differentiation, development and metabolism, and plays a functional role in adipogenesis. Studies also suggest that natural PPARγ agonists found in foods may be beneficial ant-inflammatory agents. Rosiglitazone, also known as BRL 49653, is a thiazolidinedione derivative effective in increasing insulin sensitivity in muscle and adipose tissue, as well as inducing adipocyte differentiation in pluripotent C3H10T1/2 stem cells.


References

1. Cantello, B.C., et al. 1994. J. Med. Chem. 37: 3977-3985. PMID: 7966158
2. Lehmann, J.M., et al. 1995. J. Biol. Chem. 270: 12953-12956. PMID: 7768881
3. Willson, T.M., et al. 1996. J. Med. Chem. 39: 665-668. PMID: 8576907
4. Balfour, J.A. and Plosker, G.L. 1999. Drugs. 57: 921-931. PMID: 10400405
5. Werner, A.L., et al. 2001. Pharmacotherapy. 21: 1082-1099. PMID: 11560198
6. Setti, G., et al. 2010. Am J Nephrol. 32 393-402. PMID: 20814199
7. Yoon, S.Y., et al. 2010. Neurobiol. Dis. 40: 449-455. PMID: 20655383
8. Bocciardi, R. and Ravazzolo, R. 2010. PPAR Res. 2010: 541927. PMID: 20613955

Physical State :
Solid
Solubility :
Soluble in DMSO (72 mg/ml at 25° C), methanol, water (<1 mg/ml at 25° C), ethanol (<1 mg/ml at 25° C), and DMF (~25 mg/ml).
Storage :
Store at 4° C
Melting Point :
153-155° C
Boiling Point :
584.98° C at 760 mmHg (Predicted)
Density :
1.32 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
PPARα: IC50 = >5 nM (human); PPARδ: IC50 = >5 nM (human); PPARγ: IC50 = 43 nM (human); MAO-B: IC50 = 0.83 µM (human); CA II: IC50 = 4.07 µM (human)
Ki Data :
PPARγ: Ki= 8 nM (human); MAO-B: Ki= 4.2 µM (human); Monoamine oxidase B: Ki= 5.8 µM (rat); RARγ: Ki= 10 µM (human); MAO-A: Ki= 27.6 µM (human)
pK Values :
pKa: 6.34 (Predicted), pKb: 6.5 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
77999
Merck Index :
14: 8265
MDL Number :
MFCD00871760
Beilstein Registry :
7082202
SMILES :
CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3

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Certificate of Analysis

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Rosiglitazone  Product Citations

See how others have used Rosiglitazone. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 22 total

PMID: # 31201956  Bu, J.|Wu, Y.|Cai, X.|Jiang, N.|Jeyalatha, MV.|Yu, J.|He, X.|He, H.|Guo, Y.|Zhang, M.|Quantock, AJ.|Liu, Z.|Li, W.| et al. 2019. Ocul Surf.

PMID: # 31281493  Feng, Z.|Wei, Y.|Zhang, Y.|Qiu, Y.|Liu, X.|Su, L.|Liang, N.|Yin, H.|Ding, Q.| et al. 2019. Theranostics. 9: 3501-3514.

PMID: # 29174331  Ruetz, T.|Pfisterer, U.|Di Stefano, B.|Ashmore, J.|Beniazza, M.|Tian, TV.|Kaemena, DF.|Tosti, L.|Tan, W.|Manning, JR.|Chantzoura, E.|Ottosson, DR.|Collombet, S.|Johnsson, A.|Cohen, E.|Yusa, K.|Linnarsson, S.|Graf, T.|Parmar, M.|Kaji, K.| et al. 2017. Cell Stem Cell. 21: 791-805.e9.

PMID: # 28133512  Lee, YS. et al. 2017. Toxicol Res. 33: 43-48.

PMID: # 28873424  Pfuhlmann, K.|Pfluger, PT.|Schriever, SC.|Müller, TD.|Tschöp, MH.|Stemmer, K.| et al. 2017. PLoS ONE. 12: e0183488.

PMID: # 28687706  Brun, J.|Berthou, F.|Trajkovski, M.|Maechler, P.|Foti, M.|Bonnet, N.| et al. 2017. Diabetes. 66: 2541-2554.

PMID: # 28352317  Cheng, L. et al. 2017. Exp Ther Med. 13: 467-474.

PMID: # 27382365  Gómez, D. et al. 2016. PPAR Res. 2016: 4049373.

PMID: # 27057173  El-Kehdy, H. et al. 2016. Stem cells international. 2016: 6323486.

PMID: # 25907448  Lecca, D. et al. 2015. Neuroscience. 302: 23-35.

Citations 1 to 10 of 22 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. Rosiglitazone, sc-202795, is a white to off-&shy;white&nbsp;crystalline powder.
Answered by: Chemical Support 4
Date published: 2017-03-10
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Rated 5 out of 5 by from Karakasilioti Karakasilioti, et. al. (PubMed ID 24011075) utilized SCBT product sc-202795 to activate PPAR in MMC-treated adipocytes; found that this had a marked abrogation of transcriptional induction of Il6, TNF and Kc mRNA levels. -SCBT Publication Review
Date published: 2015-04-20
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