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SML0896

Sigma-Aldrich

MCC-555

≥98% (HPLC)

Synonyme(s) :

5-[[6-[(2-Fluorophenyl)methoxy]-2-naphthalenyl]methyl]-2,4-thiazolidinedione, Isaglitazone, Netoglitazone, RWJ 241947

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About This Item

Formule empirique (notation de Hill):
C21H16FNO3S
Numéro CAS:
161600-01-7
Poids moléculaire :
381.42
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 10 mg/mL, clear

Température de stockage

2-8°C

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)

Clé InChI

PKWDZWYVIHVNKS-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H410

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

M J Reginato et al.
The Journal of biological chemistry, 273(49), 32679-32684 (1998-11-26)
Thiazolidinediones (TZDs) constitute an exciting new class of antidiabetic compounds, which function as activating ligands for peroxisome proliferator-activated receptor gamma (PPARgamma). Until now, there has been an excellent correlation between in vivo hypoglycemic potency and in vitro binding and activation
S Ulrich et al.
Experimental cell research, 310(1), 196-204 (2005-08-23)
Histone deacetylase-inhibitors affect growth and differentiation of intestinal epithelial cells by inducing expression of several transcription factors, e.g. Peroxisome proliferator-activated receptor gamma (PPARgamma) or vitamin D receptor (VDR). While activation of VDR by butyrate mainly seems to be responsible for
Kyung-Won Min et al.
Toxicology and applied pharmacology, 263(2), 225-232 (2012-07-04)
MCC-555 is a novel PPARα/γ dual ligand of the thiazolidinedione class and was recently developed as an anti-diabetic drug with unique properties. MCC-555 also has anti-proliferative activity through growth inhibition and apoptosis induction in several cancer cell types. Our group
L Pickavance et al.
British journal of pharmacology, 125(4), 767-770 (1998-12-01)
1. Young (6-week-old) pre-diabetic Zucker Diabetic Fatty (ZDF) rats displaying impaired glucose tolerance (IGT), moderate hyperglycaemia and hyperinsulinaemia were treated with the novel thiazolidinedione, MCC-555, for 28 days, during which time beta-cell failure and progression to overt diabetes occurs. 2.
L S Liu et al.
Endocrinology, 139(11), 4531-4539 (1998-10-30)
Freshly isolated adult rat ventricular cardiomyocytes have been used to characterize the action profile of the new thiazolidinedione antidiabetic drug MCC-555. Preincubation of cells with the compound (100 microM for 30 min or 10 microM for 2 h) did not
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