Netoglitazone
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MedKoo CAT#: 319622

CAS#: 161600-01-7

Description: Netoglitazone, also known as isaglitazone and MCC-555, is an agent belonging to the glitazone class of antidiabetic agents with antihyperglycemic activity. Netoglitazone exerts both peroxisome proliferator-activated receptor (PPAR) alpha and gamma agonist activity. Netoglitazone decreases bone formation and increases marrow adipocyte formation in vivo.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 240 2 Weeks
25mg USD 600 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-31. Prices are subject to change without notice.

Netoglitazone, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319622
Name: Netoglitazone
CAS#: 161600-01-7
Chemical Formula: C21H16FNO3S
Exact Mass: 381.0835
Molecular Weight: 381.4214
Elemental Analysis: C, 66.13; H, 4.23; F, 4.98; N, 3.67; O, 12.58; S, 8.41


Synonym: MCC-555; MCC 555; MCC555; RWJ-241947; RWJ 241947; RWJ241947; isaglitazone; Netoglitazone.

IUPAC/Chemical Name: 5-((6-((2-fluorophenyl)methoxy)-2-naphthalenyl)methyl)-2,4-thiazolidinedione

InChi Key: PKWDZWYVIHVNKS-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)

SMILES Code: O=C(N1)SC(CC2=CC=C3C=C(OCC4=CC=CC=C4F)C=CC3=C2)C1=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: van de Vyver M, Andrag E, Cockburn IL, Ferris WF. Thiazolidinedione-induced lipid droplet formation during osteogenic differentiation. J Endocrinol. 2014 Nov;223(2):119-32. doi: 10.1530/JOE-14-0425. Epub 2014 Sep 10. PubMed PMID: 25210048.

2: Imchen T, Manasse J, Min KW, Baek SJ. Characterization of PPAR dual ligand MCC-555 in AOM-induced colorectal tumorigenesis. Exp Toxicol Pathol. 2013 Sep;65(6):919-24. doi: 10.1016/j.etp.2013.01.005. Epub 2013 Jan 29. PubMed PMID: 23369238; PubMed Central PMCID: PMC3644347.

3: Min KW, Zhang X, Imchen T, Baek SJ. A peroxisome proliferator-activated receptor ligand MCC-555 imparts anti-proliferative response in pancreatic cancer cells by PPARgamma-independent up-regulation of KLF4. Toxicol Appl Pharmacol. 2012 Sep 1;263(2):225-32. doi: 10.1016/j.taap.2012.06.014. Epub 2012 Jun 30. PubMed PMID: 22750490; PubMed Central PMCID: PMC3443873.

4: Gijsbers L, Man HY, Kloet SK, de Haan LH, Keijer J, Rietjens IM, van der Burg B, Aarts JM. Stable reporter cell lines for peroxisome proliferator-activated receptor γ (PPARγ)-mediated modulation of gene expression. Anal Biochem. 2011 Jul 1;414(1):77-83. doi: 10.1016/j.ab.2011.02.032. Epub 2011 Feb 24. PubMed PMID: 21354099.

5: Cekanova M, Lee SH, McEntee MF, Baek SJ. MCC-555-induced NAG-1 expression is mediated in part by KLF4. Eur J Pharmacol. 2010 Jul 10;637(1-3):30-7. doi: 10.1016/j.ejphar.2010.03.055. Epub 2010 Apr 10. PubMed PMID: 20385121; PubMed Central PMCID: PMC2878920.

6: Sun N, Lu G, Lin M, Fan G, Wu Y. High-throughput quantification of a novel thiazolidinedione MCC-555 in rat plasma by ultra-fast liquid chromatography and its application in pharmacokinetic studies. Talanta. 2009 Apr 30;78(2):506-12. doi: 10.1016/j.talanta.2008.11.044. Epub 2008 Dec 6. PubMed PMID: 19203616.

7: Yamaguchi K, Cekanova M, McEntee MF, Yoon JH, Fischer SM, Renes IB, Van Seuningen I, Baek SJ. Peroxisome proliferator-activated receptor ligand MCC-555 suppresses intestinal polyps in ApcMin/+ mice via extracellular signal-regulated kinase and peroxisome proliferator-activated receptor-dependent pathways. Mol Cancer Ther. 2008 Sep;7(9):2779-87. doi: 10.1158/1535-7163.MCT-08-0173. PubMed PMID: 18790758; PubMed Central PMCID: PMC2597004.

8: Kershaw EE, Schupp M, Guan HP, Gardner NP, Lazar MA, Flier JS. PPARgamma regulates adipose triglyceride lipase in adipocytes in vitro and in vivo. Am J Physiol Endocrinol Metab. 2007 Dec;293(6):E1736-45. Epub 2007 Sep 11. PubMed PMID: 17848638; PubMed Central PMCID: PMC2819189.

9: Giaginis C, Theocharis S, Tsantili-Kakoulidou A. Investigation of the lipophilic behaviour of some thiazolidinediones. Relationships with PPAR-gamma activity. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Oct 1;857(2):181-7. Epub 2007 Jul 13. PubMed PMID: 17660053.

10: Chang F, Jaber LA, Berlie HD, O'Connell MB. Evolution of peroxisome proliferator-activated receptor agonists. Ann Pharmacother. 2007 Jun;41(6):973-83. Epub 2007 May 22. Review. PubMed PMID: 17519293.

11: Richard CL, Blay J. Thiazolidinedione drugs down-regulate CXCR4 expression on human colorectal cancer cells in a peroxisome proliferator activated receptor gamma-dependent manner. Int J Oncol. 2007 May;30(5):1215-22. PubMed PMID: 17390024.

12: Yamaguchi K, Lee SH, Eling TE, Baek SJ. A novel peroxisome proliferator-activated receptor gamma ligand, MCC-555, induces apoptosis via posttranscriptional regulation of NAG-1 in colorectal cancer cells. Mol Cancer Ther. 2006 May;5(5):1352-61. PubMed PMID: 16731769.

13: Sun N, Lin M, Fan G, Hong Z, Lu G. Quantitative determination of MCC-555, a novel insulin sensitizer in beagle dog plasma by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 May 1;835(1-2):35-9. Epub 2006 Mar 24. PubMed PMID: 16563883.

14: Takaki K, Mitsuyama K, Tsuruta O, Toyonaga A, Sata M. Attenuation of experimental colonic injury by thiazolidinedione agents. Inflamm Res. 2006 Jan;55(1):10-5. PubMed PMID: 16328104.

15: Lazarenko OP, Rzonca SO, Suva LJ, Lecka-Czernik B. Netoglitazone is a PPAR-gamma ligand with selective effects on bone and fat. Bone. 2006 Jan;38(1):74-84. Epub 2005 Aug 30. PubMed PMID: 16137931; PubMed Central PMCID: PMC1850100.

16: Kurebayashi S, Xu X, Ishii S, Shiraishi M, Kouhara H, Kasayama S. A novel thiazolidinedione MCC-555 down-regulates tumor necrosis factor-alpha-induced expression of vascular cell adhesion molecule-1 in vascular endothelial cells. Atherosclerosis. 2005 Sep;182(1):71-7. Epub 2005 Mar 4. PubMed PMID: 16115476.

17: Ulrich S, Wächtershäuser A, Loitsch S, von Knethen A, Brüne B, Stein J. Activation of PPARgamma is not involved in butyrate-induced epithelial cell differentiation. Exp Cell Res. 2005 Oct 15;310(1):196-204. PubMed PMID: 16112107.

18: Kumagai T, Ikezoe T, Gui D, O'Kelly J, Tong XJ, Cohen FJ, Said JW, Koeffler HP. RWJ-241947 (MCC-555), a unique peroxisome proliferator-activated receptor-gamma ligand with antitumor activity against human prostate cancer in vitro and in beige/nude/ X-linked immunodeficient mice and enhancement of apoptosis in myeloma cells induced by arsenic trioxide. Clin Cancer Res. 2004 Feb 15;10(4):1508-20. PubMed PMID: 14977855.

19: Pickavance LC, Widdowson PS, Foster JR, Williams G, Wilding JP. Chronic treatment with the thiazolidinedione, MCC-555, is associated with reductions in nitric oxide synthase activity and beta-cell apoptosis in the pancreas of the Zucker Diabetic Fatty rat. Int J Exp Pathol. 2003 Apr;84(2):83-9. PubMed PMID: 12801282; PubMed Central PMCID: PMC2517543.

20: Yamanouchi T. [KRP-297, MCC-555]. Nihon Rinsho. 2001 Nov;59(11):2200-6. Review. Japanese. PubMed PMID: 11712408.