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C3974

Sigma-Aldrich

Ciglitizone

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C18H23NO3S
CAS-Nummer:
74772-77-3
Molekulargewicht:
333.45
MDL-Nummer:
MFCD00865499
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24892661
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Ersteller

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)

InChIKey

YZFWTZACSRHJQD-UHFFFAOYSA-N

Angaben zum Gen

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

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Analysenzertifikate (COA)

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3-Isobutyl-1-methylxanthin ≥99% (HPLC), powder

Sigma-Aldrich

I5879

3-Isobutyl-1-methylxanthin

Dexamethason powder, BioReagent, suitable for cell culture, ≥97%

Sigma-Aldrich

D4902

Dexamethason

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)
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
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
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
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
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