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Troglitazone

Troglitazone Struktur
97322-87-7
CAS-Nr.
97322-87-7
Englisch Name:
Troglitazone
Synonyma:
ci991;CS-045;Noscal;Prelay;rezulin;Depotox;Romozin;gr92132x;AKOS 91980;ROMGLIZONE
CBNumber:
CB0486895
Summenformel:
C24H27NO5S
Molgewicht:
441.54
MOL-Datei:
97322-87-7.mol

Troglitazone Eigenschaften

Schmelzpunkt:
184-186°C
Siedepunkt:
657.0±55.0 °C(Predicted)
Dichte
1.266±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
L?slichkeit
DMSO: 20 mg/mL
Aggregatzustand
solid
pka
6.34±0.50(Predicted)
Farbe
white to yellow
Stabilit?t:
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.
InChIKey
GXPHKUHSUJUWKP-UHFFFAOYSA-N
CAS Datenbank
97322-87-7(CAS DataBase Reference)

Sicherheit

S-S?tze: 22-24/25
WGK Germany  2
RTECS-Nr. XJ5813130
HS Code  29145090

Troglitazone Chemische Eigenschaften,Einsatz,Produktion Methoden

S-S?tze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.

Beschreibung

Rezulin was launched in Japan, the UK (subseqently withdrawn) and the US for treatment of type Ⅱ diabetes.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

Chemische Eigenschaften

Crystalline Solid

History

Troglitazone (Sankyo) was firstly approved 1995 in Japan and 1997 in USA and UK. It was launched in these countries in 1997. The recommended starting dose was 400 mg/d and the highest dose 600 mg. After being marketed, the daily practice revealed adverse events in the liver with cases of fatal liver failure. This lead to withdrawal of troglitazone from the market in the UK already after two months, in USA and Japan in the year 2000.

Verwenden

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

Allgemeine Beschreibung

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.

Biologische Aktivit?t

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.

Pharmakologie

Depending on the animal model, after repeated dosing troglitazone lowered hyperglycemia as well as levels of free fatty acids, triglycerides, and insulin at daily doses of 50 mg/kg p.o. or slightly lower.

Troglitazone Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Troglitazone Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 189)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 965 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 904 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 49374 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12835 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Career Henan Chemica Co
+86-0371-86658258 +8613203830695
laboratory@coreychem.com China 30239 58
Finetech Industry Limited
+86-27-87465837 +8618971612321
info@finetechnology-ind.com China 9639 58
Baoji Guokang Bio-Technology Co., Ltd.
0917-3909592 13892490616
gksales1@gk-bio.com China 9312 58
Hefei Hirisun Pharmatech Co., Ltd
+8615056975894
shawn@hirisunpharm.com CHINA 9911 58

97322-87-7()Verwandte Suche:


  • Troglitazone(CS-045)
  • RESULIN(TM)
  • ROMGLIZONE
  • 5-(4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2
  • ci991
  • enzopyran-2-yl)methoxy)phenyl)methyl)-
  • gr92132x
  • rezulin
  • CS-045
  • CI-991,NOSCAL
  • AKOS 91980
  • (+/-)-5-[4-[(6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-YL)METHOXY]BENZYL]-2,4-THIAZOLIDINEDIONE
  • 5-[[4-[(3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2-YL)METHOXY]-PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE
  • 5-[[4-((3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2-YL)METHOXY)PHENYL]METHYL]-2,4-TH
  • 5-[[4-[(3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2-YL)METHOXY]PHENYL]METHYL]-2,4-THIOAZOLIDINEDIONE
  • TROGLITAZONE
  • 2,4-thiazolidinedione,5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-b
  • TroglitazoneMesylate
  • 5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]-phenyl]methyl]-2,4-thiazolidinedione, Romglizone, CS-045, CI-991,Noscal,
  • Troglitazone for research
  • CS-045, (±)-5-[4-[(6-Hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl]-2,4-thiazolidinedione
  • 5-(4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]benzyl)thiazolidine-2,4-dione
  • 5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-y1)methoxy]phenyl]methyl]-2.4-thiazolidinedione
  • 2,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl) methoxy)phenyl)methyl)
  • 5-[[4-[(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy]phenyl]methyl]-2,4-thiazolidinedione
  • Depotox
  • Noscal
  • Troglitazone(Rezulin)
  • Troglitazone, >=98%
  • Troglitazone Solution, 100ppm
  • Troglitazone ((±
  • Prelay
  • Romozin
  • 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
  • 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl
  • Troglitazone - CAS 97322-87-7 - Calbiochem
  • CS-045|||Romozin|||Rezulin|||Romglizone|||Noscal|||Prelay
  • 97322-87-7
  • 97332-87-7
  • 7322-87-7
  • C24H27NO5S
  • C25H29NO4S
  • PPAR and RXR Regulators
  • Gene Regulation and Expression
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Intracellular receptor
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Active Pharmaceutical Ingredients
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds
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