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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

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Certificates of Analysis (COA)

Lot/Batch Number
123M4709V

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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
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
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.
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
R Upton et al.
British journal of pharmacology, 125(8), 1708-1714 (1999-01-14)
1. We examined the effect of chronic (21 days) oral treatment with the thiazolidinedione, MCC-555 ((+)-5-[[6-(2-fluorbenzyl)-oxy-2-naphy]methyl]-2,4-thiazo lid inedione) on metabolic status and insulin sensitivity in obese (fa/fa) Zucker rats and Zucker Diabetic Fatty (ZDF) rats which display an impaired glucose
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