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Troglitazone

Troglitazone
Troglitazone structure
CAS No.
97322-87-7
Chemical Name:
Troglitazone
Synonyms
ci991;Noscal;CS-045;Prelay;Depotox;rezulin;Romozin;gr92132x;ROMGLIZONE;AKOS 91980
CBNumber:
CB0486895
Molecular Formula:
C24H27NO5S
Formula Weight:
441.54
MOL File:
97322-87-7.mol

Troglitazone Properties

Melting point:
184-186°C
Boiling point:
657.0±55.0 °C(Predicted)
Density 
1.266±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
DMSO: 20 mg/mL
form 
solid
pka
6.34±0.50(Predicted)
color 
white to yellow
InChIKey
GXPHKUHSUJUWKP-UHFFFAOYSA-N
CAS DataBase Reference
97322-87-7(CAS DataBase Reference)
FDA UNII
I66ZZ0ZN0E
NCI Drug Dictionary
Prelay
ATC code
A10BG01
SAFETY
  • Risk and Safety Statements
Safety Statements  22-24/25
WGK Germany  2
RTECS  XJ5813130
HS Code  29145090

Troglitazone price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 648469-M Troglitazone 97322-87-7 5mg-m $169 2021-12-16 Buy
Sigma-Aldrich T2573 Troglitazone ≥98% (HPLC) 97322-87-7 5 mg $143 2021-12-16 Buy
Cayman Chemical 71750 Troglitazone ≥98% 97322-87-7 5mg $47 2021-12-16 Buy
Cayman Chemical 71750 Troglitazone ≥98% 97322-87-7 10mg $89 2021-12-16 Buy
Tocris 3114 Troglitazone ≥97%(HPLC) 97322-87-7 10 $151 2021-12-16 Buy

Troglitazone Chemical Properties,Uses,Production

Description

Rezulin was launched in Japan, the UK (subseqently withdrawn) and the US for treatment of type Ⅱ diabetes.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 Properties

Crystalline Solid

Originator

Sankyo (Japan)

Uses

Troglitazone is an an oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Antidiabetic.

Uses

antidiabetic;peroxisome proliferator-activated receptors activator

Uses

Troglitazone 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 Process

A 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 name

Prelay (Sankyo); Rezulin (Pfizer);Ronglitazone.

Therapeutic Function

Hypoglycemic

General Description

A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ). Also exhibits anti-proliferative and anti-inflammatory properties. Shown to induce cell cycle arrest and apoptosis in human hepatoma cells. Inhibits vascular smooth muscle cell (VSMC) migration by rapidly activating MEK/ERK pathway leading to the induction of c-fos and Ets-1 expression. Blocks PDGF-induced cell proliferation of pancreatic stellate and accelerates p21Cip1 turnover by inhibiting PKCδ signaling in VSMCs. Exerts positive inotropic effect via Ca2+ sensitization in the sarcoplasmic reticulum and inhibits Na+/H+ exchange activity and proliferation of macrovascular endothelial cells.

Biological Activity

Selective 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.

Biochem/physiol Actions

Primary TargetPeroxisome proliferator-activated receptors γ (PPARγ)

Troglitazone Preparation Products And Raw materials

Raw materials

Preparation Products


Troglitazone Suppliers

Global( 155)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 914 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com China 47498 58
Zhuozhou Wenxi import and Export Co., Ltd
+8613111626072 (WhatsApp)
Wechat: +8613111626072 Wickr me: waynehu zzwenxi@126.com CHINA 13187 58
Target Molecule Corp
18019718960 781-999-5354
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Career Henan Chemica Co
15093356674 0371-55982848
0371-86658258 laboratory@coreychem.com CHINA 30290 58
Baoji Guokang Bio-Technology Co., Ltd.
09173909592
09173909592 cngksw@aliyun.com CHINA 9432 58

View Lastest Price from Troglitazone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-13 Troglitazone
97322-87-7
US $39.00 / KG 1g 99.9% 500000kgs Shijiazhuang tongyang Import and Export Co., LTD
2021-08-12 Troglitazone
97322-87-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
2021-07-13 Troglitazone
97322-87-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

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