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Troglitazone

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Troglitazone Basic information
Troglitazone Chemical Properties
  • Melting point:184-186°C
  • Boiling point:657.0±55.0 °C(Predicted)
  • Density 1.266±0.06 g/cm3(Predicted)
  • storage temp. Store at -20°C
  • solubility DMSO: 20 mg/mL
  • pka6.34±0.50(Predicted)
  • form solid
  • color white to yellow
  • InChIKeyGXPHKUHSUJUWKP-UHFFFAOYSA-N
  • CAS DataBase Reference97322-87-7(CAS DataBase Reference)
Safety Information
  • Safety Statements 22-24/25
  • WGK Germany 2
  • RTECS XJ5813130
  • HS Code 29145090
MSDS
Troglitazone Usage And Synthesis
  • DescriptionRezulin was launched in Japan, the UK (subseqently withdrawn) and the US for treatment of type Ⅱ diabetes. Two approaches, four steps and six steps, converge on 6-acetoxy-2-(4-aminophenoxymethyl)-2,5,7,8-tetramethylchroman which can be elaborated in two steps to Rezulin. It is the first of a new class of thiazolidenediones for NIDDM that reduces glucose concentrations without effecting insulin secretion. It binds to peroxisome proliferator-activated receptor gamma (PPARγ) thus activating this nuclear receptor which then influences carbohydrate metabolism. This is accomplished by increasing insulin sensitivity by upregulating glucose transporter (Glut1 and/or Glut4) expression without affecting the number or affinity of insulin receptors. There is also an increase in hepatic glycogen synthase activity which enhances glucose utilization and a reduction in hepatic gluconeogenesis by inhibiting fructose-1 ,&bisphosphatase. Pancreatic islet cell destruction is prevented. It reduces serum triglycerides because PPARγ causes fibroblasts to differentiate into adipocytes and does not activate RARα. It has a half-life of 9 h and is metabolized into three compounds having no activity.
  • Chemical PropertiesCrystalline Solid
  • OriginatorSankyo (Japan)
  • UsesTroglitazone is an an oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Antidiabetic.
  • Usesantidiabetic;peroxisome proliferator-activated receptors activator
  • UsesTroglitazone is a TZD which was approved for the treatment of insulin resistance and hyperglycemia in Type II diabetes, under the trade name Resulin?, but was withdrawn from the market due to hepatotoxicity. Troglitazone is a potent and selective PPARγ agonist. The EC50 values for transactivation of human and mouse PPARγ in a cell-based assay are 0.55 and 0.78 μM, respectively. In the same assay system, no activation of PPARα and PPARδ was observed at concentrations up to 10 μM. Troglitazone binds to the PPARγ ligand-binding domain (LBD) but fails to induce interaction of the PPARγ LBD with the transcriptional coactivators SRC-1, TIF2, AIB1, p300, or TRAP220. Troglitazone also induces cell cycle arrest and apoptosis in several cancer cell lines with an EC50 of 10 μM.
  • Manufacturing ProcessA mixture of 70 g of ethyl-3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2- ylmethoxy)phenyl]-2-chloropropionate, 13.12 g of thiourea and 80.2 ml of sulpholane was reacted for 80 min, under a nitrogen stream at 115°-120°C. Subsequently, a 656.2 ml acetic acid, 218.7 ml conc. hydrochloric acid and 109.4 ml water was added to this and the resulting mixture was further heated for 12 h at 85°-90°C. The reaction mixture was cooled to room temperature and 196.8 g of sodium bicarbonate was added and once the evolution of carbondioxide had ceased, the solvent was distilled off applying high vacuum. A 10:1 by volume mixture of benzene and ethyl acetate was added to the residue and the crude product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution water. The organic layer was dried over anhydrous sodium sulphate and the solvent was distilled off. The resulting crude product was quickly eluted from a silica gel column with 50% ethylacetate-hexane to furnish 40 g of the required 5-{4- (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzyl)thiazolidine-2,4- dione (Troglitazone) with a HPLC purity of about 67-70%. The elution of column was continued further to yield 5-[4-(6-hydroxy-2,5,7,8- tetramethylchroman-2-yl-methoxy)benzyl]-2-iminothiazolidine-4-one with HPLC purity of about 70%.
  • brand namePrelay (Sankyo); Rezulin (Pfizer);Ronglitazone.
  • Therapeutic FunctionHypoglycemic
  • Biological ActivitySelective PPAR γ receptor agonist (EC 50 values are 780 and 555 nM at murine and human PPAR γ receptors respectively). Displays no activity at PPAR α or PPAR δ receptors. Antidiabetic agent; exerts potent glucose-lowering effects in insulin-resistant diabetic mice. Displays anti-invasive effect on human breast cancer cells; reduces migration, adhesion and spreading on fibronectin-coated plates. Also inhibits lamellipodia formation and actin polymerization.
Troglitazone Preparation Products And Raw materials
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