C3974

Sigma-Aldrich

Ciglitizone

≥98% (HPLC)

Synonym(s):
(±)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione, Ciglitazone
Empirical Formula (Hill Notation):
C18H23NO3S
CAS Number:
Molecular Weight:
333.45
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

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.

Packaging

5 mg in glass insert

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

S Zulkafli Nor Effa et al.
Biomolecules, 8(4) (2018-11-08)
Immunomodulation, as a means of immunotherapy, has been studied in major research and clinical laboratories for many years. T-Regulatory (Treg) cell therapy is one of the modulators used in immunotherapy approaches. Similarly, nuclear receptor peroxisome proliferator activated receptor gamma (PPARγ)...
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...
H Y Kang et al.
The British journal of dermatology, 150(3), 462-468 (2004-03-20)
Peroxisome proliferator-activated receptors (PPARs) belong to the superfamily of nuclear receptors that heterodimerize with the retinoic X receptor. Agonists of PPAR have been known to play an important role in cellular responses including proliferation and differentiation. The expression and function...
B C Cantello et al.
Journal of medicinal chemistry, 37(23), 3977-3985 (1994-11-11)
A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a...
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