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.

Chemical Structure

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Netoglitazone
CAS# 161600-01-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319622
Name: Netoglitazone
CAS#: 161600-01-7
Chemical Formula: C21H16FNO3S
Exact Mass: 381.08
Molecular Weight: 381.421
Elemental Analysis: C, 66.13; H, 4.23; F, 4.98; N, 3.67; O, 12.58; S, 8.41

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 weeks
25mg USD 650 2 weeks
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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

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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Netoglitazone is a dual agonist of PPARα and PPARγ with antihyperglycemic activity.
In vitro activity: In this study, the pro-adipocytic and anti-osteoblastic activities of netoglitazone were evaluated in vitro, using both U-33/gamma2 cells as a model of marrow mesenchymal cell differentiation under the control of PPAR-gamma2 and primary bone marrow cultures, and in vivo in C57BL/6 mice. In vitro, netoglitazone induced adipocyte and inhibited osteoblast formation in a PPAR-gamma2-dependent manner; however, it was 100-fold less effective than rosiglitazone. Reference: Bone. 2006 Jan;38(1):74-84. https://pubmed.ncbi.nlm.nih.gov/16137931/
In vivo activity: This study found that MCC-555 suppressed AOM-induced ACF in A/J mice, compared to the control group. Administration of MCC-555 resulted in decreased mitoses and increased apoptotic cells in the colon. Furthermore, expression of tumor suppressor protein MUC2 was increased in MCC-555 treated mice. Reference: Exp Toxicol Pathol. 2013 Sep;65(6):919-24. https://pubmed.ncbi.nlm.nih.gov/23369238/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 140.0 367.05
DMSO:PBS (pH 7.2) (1:1) 1.0 2.62
Ethanol 1.0 2.62

Preparing Stock Solutions

The following data is based on the product molecular weight 381.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Chen CY, Tseng KY, Wong ZH, Chen YP, Chen TY, Chen HY, Chen ZY, Lin FH, Wu HM, Lin S. Cooperative impact of thiazolidinedione and fatty acid synthase on human osteogenesis. Aging (Albany NY). 2019 Apr 20;11(8):2327-2342. doi: 10.18632/aging.101916. PMID: 31005954; PMCID: PMC6519991. 2. 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. doi: 10.1016/j.bone.2005.07.008. Epub 2005 Aug 30. PMID: 16137931; PMCID: PMC1850100. 3. 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. PMID: 23369238; PMCID: PMC3644347. 4. 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. PMID: 20385121; PMCID: PMC2878920.
In vitro protocol: 1. Chen CY, Tseng KY, Wong ZH, Chen YP, Chen TY, Chen HY, Chen ZY, Lin FH, Wu HM, Lin S. Cooperative impact of thiazolidinedione and fatty acid synthase on human osteogenesis. Aging (Albany NY). 2019 Apr 20;11(8):2327-2342. doi: 10.18632/aging.101916. PMID: 31005954; PMCID: PMC6519991. 2. 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. doi: 10.1016/j.bone.2005.07.008. Epub 2005 Aug 30. PMID: 16137931; PMCID: PMC1850100.
In vivo protocol: 1. 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. PMID: 23369238; PMCID: PMC3644347. 2. 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. PMID: 20385121; PMCID: PMC2878920.

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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.