For research use only. Not for therapeutic Use.
Netoglitazone（Cat No.:R034321）, 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.
| Catalog Number | R034321 |
| CAS Number | 161600-01-7 |
| Synonyms | 5-[[6-[(2-Fluorophenyl)methoxy]-2-naphthalenyl]methyl]-2,4-thiazolidinedione; Isaglitazone; Netoglitazone; RWJ 241947 |
| Molecular Formula | C21H16FNO3S |
| Purity | ≥95% |
| Target | Vitamin D Related/Nuclear Receptor |
| Solubility | Soluble in DMSO |
| Storage | 2-8°C |
| IUPAC Name | 5-[[6-[(2-fluorophenyl)methoxy]naphthalen-2-yl]methyl]-1,3-thiazolidine-2,4-dione |
| InChI | 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) |
| InChIKey | PKWDZWYVIHVNKS-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C(=C1)COC2=CC3=C(C=C2)C=C(C=C3)CC4C(=O)NC(=O)S4)F |
| Reference | </br>1:Characterization of PPAR dual ligand MCC-555 in AOM-induced colorectal tumorigenesis. Imchen T, Manasse J, Min KW, Baek SJ.Exp Toxicol Pathol. 2013 Sep;65(6):919-24. doi: 10.1016/j.etp.2013.01.005. Epub 2013 Jan 29. PMID: 23369238 Free PMC Article</br>2:A peroxisome proliferator-activated receptor ligand MCC-555 imparts anti-proliferative response in pancreatic cancer cells by PPARgamma-independent up-regulation of KLF4. Min KW, Zhang X, Imchen T, Baek SJ.Toxicol Appl Pharmacol. 2012 Sep 1;263(2):225-32. doi: 10.1016/j.taap.2012.06.014. Epub 2012 Jun 30. PMID: 22750490 Free PMC Article</br>3:MCC-555-induced NAG-1 expression is mediated in part by KLF4. Cekanova M, Lee SH, McEntee MF, Baek SJ.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 Free PMC Article</br>4:Subchronic toxicity and toxicokinetics of MCC-555, a novel thiazolidinedione, after 270-day repeated oral administration in dogs. Sun N, Lu G, Lin M, Fan G, Wu Y.Environ Toxicol Pharmacol. 2009 Mar;27(2):237-46. doi: 10.1016/j.etap.2008.10.011. Epub 2008 Nov 8. PMID: 21783946 </br>5:High-throughput quantification of a novel thiazolidinedione MCC-555 in rat plasma by ultra-fast liquid chromatography and its application in pharmacokinetic studies. Sun N, Lu G, Lin M, Fan G, Wu Y.Talanta. 2009 Apr 30;78(2):506-12. doi: 10.1016/j.talanta.2008.11.044. Epub 2008 Dec 6. PMID: 19203616 </br>6: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. Yamaguchi K, Cekanova M, McEntee MF, Yoon JH, Fischer SM, Renes IB, Van Seuningen I, Baek SJ.Mol Cancer Ther. 2008 Sep;7(9):2779-87. doi: 10.1158/1535-7163.MCT-08-0173. PMID: 18790758 Free PMC Article</br>7:A novel peroxisome proliferator-activated receptor gamma ligand, MCC-555, induces apoptosis via posttranscriptional regulation of NAG-1 in colorectal cancer cells. Yamaguchi K, Lee SH, Eling TE, Baek SJ.Mol Cancer Ther. 2006 May;5(5):1352-61. PMID: 16731769 Free Article</br>8:Quantitative determination of MCC-555, a novel insulin sensitizer in beagle dog plasma by high-performance liquid chromatography with fluorescence detection. Sun N, Lin M, Fan G, Hong Z, Lu G.J Chromatogr B Analyt Technol Biomed Life Sci. 2006 May 1;835(1-2):35-9. Epub 2006 Mar 24. PMID: 16563883 </br>9:A novel thiazolidinedione MCC-555 down-regulates tumor necrosis factor-alpha-induced expression of vascular cell adhesion molecule-1 in vascular endothelial cells. Kurebayashi S, Xu X, Ishii S, Shiraishi M, Kouhara H, Kasayama S.Atherosclerosis. 2005 Sep;182(1):71-7. Epub 2005 Mar 4. PMID: 16115476 </br>10:MCC-555 (Mitsubishi-Tokyo Pharmaceuticals). Velussi M.IDrugs. 2001 May;4(5):586-9. PMID: 16012905 |
