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C3974

Sigma-Aldrich

Ciglitizone

≥98% (HPLC)

Synonym(s):

(±)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione, Ciglitazone

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About This Item

Empirical Formula (Hill Notation):
C18H23NO3S
CAS Number:
74772-77-3
Molecular Weight:
333.45
MDL number:
MFCD00865499
UNSPSC Code:
12352200
PubChem Substance ID:
24892661
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

originator

Takeda

SMILES string

CC1(CCCCC1)COc2ccc(CC3SC(=O)NC3=O)cc2

InChI

1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)

InChI key

YZFWTZACSRHJQD-UHFFFAOYSA-N

Gene Information

human ... PPARG(5468)
mouse ... Pparg(19016)

Application

Ciglitizone has been used as a proliferator-activated receptor γ (PPARγ) agonist:
  • to study its effects on cell proliferation in human melanocytes
  • to study its effects on pigmentation and migration of human melanocytes

It also may be used to study its effects on cell cycle and apoptosis in monocytic cells.

Biochem/physiol Actions

Ciglitizone belongs to the class of thiazolidinediones and is a peroxisome proliferator-activated receptor γ (PPARγ) agonist. It exhibits anti-diabetic activity. Ciglitizone has the potential to treat tumor necrosis factor α (TNFα)-related apoptosis-inducing ligand (TRAIL)-refractory high-grade urothelial cancers.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Takeda. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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N K Singh et al.
Journal of animal science, 85(5), 1126-1135 (2006-12-21)
Ciglitizone, a class of thiazolidinediones, acts as a potent activator of the adipose differentiation program in established preadipose cell lines. Thiazolidinediones have also been investigated in diabetic patients and have been reported to act as peroxisome proliferator-activated receptor-gamma ligands. Intramuscular
The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones.
T M Willson et al.
Journal of medicinal chemistry, 39(3), 665-668 (1996-02-02)
Denise M Ray et al.
Journal of immunology (Baltimore, Md. : 1950), 177(8), 5068-5076 (2006-10-04)
Peroxisome proliferator-activated receptor gamma (PPARgamma) is a transcription factor important for adipogenesis and more recently has been shown to be an anticancer target. PPARgamma ligands, including the endogenous ligand 15-deoxy-Delta12,14-PGJ2 (15d-PGJ2) and synthetic ligands like ciglitazone and troglitazone, all induce
Joong Sun Lee et al.
Experimental dermatology, 16(2), 118-123 (2007-01-16)
Peroxisome proliferator-activated receptors (PPARs) play an important role in cellular responses. It was reported that three subtypes of PPAR are expressed in human melanocytes. In this study, we investigated the effects of the PPAR-gamma agonist, ciglitazone, on pigmentation and migration
Brett McKinnon et al.
Fertility and sterility, 97(3), 657-664 (2011-12-24)
To assess the effect of thiazolidinediones on the regulation of inflammatory cytokines related to endometriosis in endometrial tissue and determine whether these effects occur via activation of the peroxisome proliferating activating receptor gamma (PPAR)-γ. In vitro study using eutopic endometrial
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