161600-01-7

Basic information

• Product Name: MCC-555
• Synonyms: 5-[[6-[(2-FLUOROPHENYL)METHOXY]-2-NAPHTHALENYL]METHYL]-2,4-THIAZOLIDINEDIONE;MCC-555;NETOGLITAZONE,2,4-THIAZOLIDINEDIONE, 5-[[6-[(2-FLUOROPHENYL)METHOXY]-2-NAPHTHALENYL]METHYL]-;Isaglitazone;Netoglitazone;RWJ 241947;5-[[6-[(2-fluorophenyl)methoxy]naphthalen-2-yl]methyl]-1,3-thiazolidine-2,4-dione
• CAS NO: 161600-01-7
• Molecular Formula: C₂₁H₁₆FNO₃S
• Molecular Weight: 381.42
• Mol File: 161600-01-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 599.5°C at 760 mmHg
• Flash Point: 316.4°C
• Appearance: white to beige/
• Density: 1.369g/cm³
• Vapor Pressure: 2.47E-14mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble10mg/mL, clear
• PKA: 6.28±0.50(Predicted)
• CAS DataBase Reference: MCC-555(CAS DataBase Reference)
• NIST Chemistry Reference: MCC-555(161600-01-7)
• EPA Substance Registry System: MCC-555(161600-01-7)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: XJ5813445
• Hazardous Substances Data: 161600-01-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 161600-01-7 differently. You can refer to the following data:
1. Antidiabetic; orally-administered insulin action enhancer to lower the plasma glucose in patients with non-insulin dependent diabetes mellitus (Type II).
2. MCC 555 belongs to the thiazolidinedion class, a group of compounds with anti-diabetic properties. In addition, MCC 555 has been found to induce apoptosis in pancreatic and colorectal cancer cells involving the?Nonsteroidal anti-inflammatory drug (NSAID)-activated gene?(NAG-1). MCC 555 is an agent with anti-diabetic and anti-cancer properties.

Biological Activity

mcc-555, also known as rwj-241947, is a novel peroxisome proliferator–activated receptor γ ligand [1].the pparγ receptors mainly express in adipose tissue, colon and macrophages involved in regulating fatty acid storage and glucose metabolism. it has been identified that pparγ is the major functional receptor for the thiazolidinedione class of insulin-sensitizing drugs. the pparγ receptor is implicated in the processes of adipogenesis and systemic insulin action [2].mcc-555 (5 μmol/l) exhibited an apoptotic activity in human colorectal cancer cells. mcc-555 significantly increased nag-1 expression in a pparγ-independent manner. in hct-116 cells, treatment with mcc-555 induced apoptosis. mcc-555 affected nag-1 mrna stability. mcc-555 treatment induced rapid phosphorylation of erk1/2 [1]. in various solid and hematological tumor cell lines, mcc-555 showed antiproliferative activity against prostate cancer cells, with the strongest effect against the androgen-independent pc-3 prostate cancer cells [2].in male beige/nude/x-linked immunodeficient (bnx) mice, treatment with mcc-555 profoundly suppressed growth of pc-3 prostate cancer xenografts with prominent apoptosis, fibrosis, and inflammatory and giant cell reaction. the experimented mice showed significantly decreased cholesterol [3].

Biochem/physiol Actions

MCC-555 is a thiazolidinedione class anti-diabetic compound. In rodent models, MCC-555 attenuates the development of diabetes, maintains B-cell function and improves insulin sensitivity. The compound MCC-555 also inhibits proliferation of several cancer cell lines and reduces tumor growth in xenograft models.

references

[1] yamaguchi k, lee s h, eling t e, et al. a novel peroxisome proliferator–activated receptor γ ligand, mcc-555, induces apoptosis via posttranscriptional regulation of nag-1 in colorectal cancer cells[j]. molecular cancer therapeutics, 2006, 5(5): 1352-1361.[2] spiegelman b m. ppar-gamma: adipogenic regulator and thiazolidinedione receptor[j]. diabetes, 1998, 47(4): 507-514.[3] kumagai t, ikezoe t, gui d, et al. rwj-241947 (mcc-555), a unique peroxisome proliferator-activated receptor-γ 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[j]. clinical cancer research, 2004, 10(4): 1508-1520.

InChI:InChI=1/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)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 161599-54-8 6-(2-fluorobenzyloxy)-2-naphthylmethyl iodide 
• 161600-03-9 5-(6-hydroxy-2-naphthyl)methyl-2,4-thiazolidinedione 
• 345-35-7 2-fluorobenzyl chloride 

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