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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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Oxana P Lazarenko et al.
Bone, 38(1), 74-84 (2005-09-03)
Thiazolidinediones are effective anti-diabetic drugs that improve insulin sensitivity through the activation of the nuclear receptor and adipocyte-specific transcription factor, peroxisome proliferator-activated receptor gamma (PPAR-gamma). Recent evidence suggests that PPAR-gamma also controls bone cell development and bone homeostasis. In mice
T Yamanouchi
Nihon rinsho. Japanese journal of clinical medicine, 59(11), 2200-2206 (2001-11-20)
KRP-297 and MCC-555, which are being developed in Japan as thiazolidinediones, uniquely bind and activate peroxisome proliferator-activated receptors(PPAR). KRP-297, unlike other thiazolidinediones, effects on not only PPAR gamma but also PPAR alpha. Furthermore, this compound acts directly on basal glucose
Ning Sun et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 835(1-2), 35-39 (2006-03-28)
A sensitive high-performance liquid chromatographic method with fluorescence detection has been developed for determination of MCC-555 (5-[[6-(2-fluorbenzyl)-oxy-2-naphy] methyl]-2,4-thiazolidinedione) in beagle dog plasma. Sample preparation was done by protein precipitation with acetonitrile and a synthetic intermediate of MCC-555 (5-[[6-(2-fluorbenzyl)-oxy-2-naphy] methylene]-2,4-thiazolidinedione) was
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
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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