C3974
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:
Molecular Weight:
333.45
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
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:
It also may be used to study its effects on cell cycle and apoptosis in monocytic cells.
- 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)
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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)
[[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents.
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
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)
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