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Key Documents

SML0896

Sigma-Aldrich

MCC-555

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H16FNO3S
CAS Number:
161600-01-7
Molecular Weight:
381.42
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

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)

InChI key

PKWDZWYVIHVNKS-UHFFFAOYSA-N

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.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cynthia Lee Richard et al.
International journal of oncology, 30(5), 1215-1222 (2007-03-29)
Peroxisome proliferator activated receptor (PPAR) gamma is a nuclear receptor involved primarily in lipid and glucose metabolism. PPARgamma is also expressed in several cancer types, and has been suggested to play a role in tumor progression. PPARgamma agonists have been
Ning Sun et al.
Talanta, 78(2), 506-512 (2009-02-11)
MCC-555 is a novel thiazolidinedione which reduces plasma glucose concentrations in Type 2 diabetes mellitus models due to enhancement of insulin sensitivity. A highly sensitive and selective quantitative method to accurately determine MCC-555 in rat plasma is crucial to the
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
C Prabhakar et al.
Bioorganic & medicinal chemistry letters, 8(19), 2725-2730 (1999-01-05)
Novel compounds having a dual pharmacophore were synthesised and evaluated for their insulin sensitiser and anti-inflammatory properties in different animal models.
Costas Giaginis et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 857(2), 181-187 (2007-07-31)
Various lipophilicity aspects of five well-known PPAR-gamma ligands, belonging to the thiazolidinedione (TZD) class, ciglitazone (CSZ), troglitazone (TGZ), netoglitazone (NGZ) and the ampholytic pioglitazone (PGZ) and rosiglitazone (RGZ), have been explored. The compounds were found to be highly lipophilic as
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