| Identification | Back Directory | [Name]
CIGLITAZONE | [CAS]
74772-77-3 | [Synonyms]
U-63287
AD-4533
ADD 3878
CIGLITAZONE
CIGLITIZONE
CIGLITLZONE
CIGLITAZONE(SUBJECTTOPATENTFREE)
5-[p-[2,2-(Pentane-1,5-diyl)propyloxy]benzyl]thiazolidine-2,4-dione
(+/-)-5-[4-(1-METHYLCYCLOHEXYLMETHOXY)BENZYL]-THIAZOLIDINE-2,4-DIONE
5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-4-thiazolidinedione
5-[[4-[(1-METHYLCYCLOHEXYL)METHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE | [Molecular Formula]
C18H23NO3S | [MDL Number]
MFCD00865499 | [MOL File]
74772-77-3.mol | [Molecular Weight]
333.45 |
| Chemical Properties | Back Directory | [Appearance]
White Cyrstalline Solid | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
White Cyrstalline Solid | [Uses]
Displays antihyperglycemic activity in genetically obese mice. It is a selective PPARg agonist | [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. | [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 . | [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. | [Originator]
Ciglitazone, synthetized by Takeda and reported in 1982, was a result of screening of clofibrate analogues for
hypolipidemic activity. | [General Description]
A potent thiazolinedione (TDZ) type anti-hyperglycemic agent and a selective PPARγ agonist (EC50 = 3 μM). | [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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