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Merck
CN

C3974

Ciglitizone

≥98% (HPLC)

别名:

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

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关于此项目

经验公式（希尔记法）:
C18H23NO3S
化学文摘社编号:
74772-77-3
分子量:
333.45
NACRES:
NA.77
PubChem Substance ID:
24892661
UNSPSC Code:
12352200
MDL number:
MFCD00865499

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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)

SMILES string

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

InChI key

YZFWTZACSRHJQD-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

originator

Takeda

Quality Level

100

Gene Information

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

相关类别

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.

存储类别

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCJ8935
MKCJ5211
MKBT4779V
MKBR9118V
099K1370V

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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
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
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
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)
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)
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