CIGLITAZONE Chemical Properties

Melting point:

130-131°C

Boiling point:

504.5±23.0 °C(Predicted)

Density 

1.189±0.06 g/cm3(Predicted)

storage temp. 

Store at RT

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).

form 

Tan solid

pka

6.36±0.50(Predicted)

color 

Tan

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

Safety Information

WGK Germany 

3

RTECS 

XJ5813700

HS Code 

29341000

MSDS

• Language:English Provider:SigmaAldrich

CIGLITAZONE Usage And Synthesis

Description

Ciglitazone (74772-77-3) is a PPARγ agonist (EC50=3 μM). Stimulates adipogenesis in human mesenchymal stem cells. Ciglitazone inhibits HUVEC differentiation and angiogenesis. Cell permeable.

Chemical Properties

White Cyrstalline Solid

Originator

Ciglitazone, synthetized by Takeda and reported in 1982, was a result of screening of clofibrate analogues for hypolipidemic activity.

Uses

Displays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist.

Uses

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.

Definition

ChEBI: An aromatic ether that consists of 1,3-thiazolidine-2,4-dione with position 5 substituted by a 4-[(1-methylcyclohexyl)methoxy]benzyl group. A selective PPARgamma agonist.

General Description

A potent thiazolinedione (TDZ) type anti-hyperglycemic agent and a selective PPARγ agonist (EC₅₀ = 3 μM).

Biological Activity

Selective agonist at PPAR γ (peroxisome proliferator-activated receptor γ ). Activates PPAR γ with an EC 50 value of 3 μ M in vitro , and is at least 33-fold selective over PPAR α and δ . Antihyperglycemic in vivo .

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.

Pharmacology

Ciglitazone reduced plasma triglycerides, hyperglycemia and hyperinsulinemia in several insulin resistant diabetic and nondiabetic rodent models after repeated oral dosing at doses of 100 – 300 mg/kg body weight, while having little or no effect in normal rodents or those with insulin deficient diabetes. In long-term animal studies lens cataracts occurred and ciglitazone development was discontinued.

storage

Room temperature

Mode of action

Ciglitizone is a thiazolidine-2,4-dione derivative. The mechanism of blood glucose lowering activity by thiazolidinedione derivatives has not been fully elucidated yet. Only minor or no effects are observed in normal animals or insulin sensitive diabetes models. In obese or hyperinsulinemic insulin resistant rodents thiazolidinediones lower insulin and triglyceride levels after treatment for 2 to 8 d. If hyperglycemia occurs, also the blood glucose concentration is reduced. Mechanistic in vitro studies with adipocytes have shown that the thiazolidinediones are ligands of the peroxisome proliferator activated receptor. Peroxisome proliferator activated receptors (PPARs) belong to the nuclear receptor superfamily of ligand-activated transcription factors. So far, three receptor subtypes have been identified: PPAR , PPAR , and PPAR . The PPARs are believed to play a physiological role in the regulation of lipid metabolism. The in vivo antihyperglycemic activity of thiazolidinediones strongly correlates with their potency as PPAR agonists in vitro.

References

1) Cantello et al. (1994) [[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents; J. Med. Chem. 37 3977 2) Xin et al. (1999) Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo; J. Biol. Chem. 274 9116

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