netoglitazone

Names

[ Name ]:
netoglitazone

[Synonym ]:
5-({6-[(2-Fluorobenzyl)oxy]-2-naphthyl}methyl)-1,3-thiazolidine-2,4-dione
2,4-Thiazolidinedione, 5-[[6-[(2-fluorophenyl)methoxy]-2-naphthalenyl]methyl]-
UNII-QOV2JZ647A
Isaglitazone
5-({6-[(2-fluorobenzyl)oxy]naphthalen-2-yl}methyl)-1,3-thiazolidine-2,4-dione
MCC-555
netoglitazone

Biological Activity

[Description]:

Netoglitazone is a dual agonist of PPARα and PPARγ with antihyperglycemic activity[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Research Areas >> Metabolic Disease

[Target]

PPARα

PPARγ

[References]

[1]. Reginato MJ, et al. A potent antidiabetic thiazolidinedione with unique peroxisome proliferator-activated receptor gamma-activating properties. J Biol Chem. 1998 Dec 4;273(49):32679-84.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
599.5±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₁₆FNO₃S

[ Molecular Weight ]:
381.420

[ Flash Point ]:
316.4±24.6 °C

[ Exact Mass ]:
381.083496

[ PSA ]:
80.70000

[ LogP ]:
4.50

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.668

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50/53

[ Safety Phrases ]:
60-61

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
XJ5813445

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

MCC-555-induced NAG-1 expression is mediated in part by KLF4.

Eur. J. Pharmacol. 637(1-3) , 30-7, (2010)

Peroxisome proliferator-activated receptor gamma (PPARgamma) plays a central role in cell differentiation, metabolism and tumorigenesis. We have investigated the therapeutic properties of 5-[[6-[(2-fl...

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. 84(2) , 83-9, (2003)

The Zucker Diabetic Fatty (ZDF) rat is a model of impaired insulin sensitivity arising from hyperphagia owing to a mutation in the leptin receptor. In time, young ZDF rats, which are not initially dia...

Activation of PPARgamma is not involved in butyrate-induced epithelial cell differentiation.

Exp. Cell Res. 310(1) , 196-204, (2005)

Histone deacetylase-inhibitors affect growth and differentiation of intestinal epithelial cells by inducing expression of several transcription factors, e.g. Peroxisome proliferator-activated receptor...