Canagliflozin
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- CAS-Nr.
- 842133-18-0
- Englisch Name:
- Canagliflozin
- Synonyma:
- Canaglifozin;Invokana;Cagliflozin;JNJ 28431754;Canaglifozion;(1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4 -methylphenyl]-D-glucitol;(2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;CS-183;TA 7284;Calaglizin
- CBNumber:
- CB02510088
- Summenformel:
- C24H25FO5S
- Molgewicht:
- 444.52
- MOL-Datei:
- 842133-18-0.mol
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Canagliflozin Eigenschaften
- Schmelzpunkt:
- 68 - 72°C
- Siedepunkt:
- 642.9±55.0 °C(Predicted)
- Dichte
- 1.364
- storage temp.
- -20°C
- L?slichkeit
- Soluble in DMSO (40 mg/ml)
- Aggregatzustand
- solid
- pka
- 13.34±0.70(Predicted)
- Farbe
- White
- Stabilit?t:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- InChIKey
- XTNGUQKDFGDXSJ-XDLHWMRXNA-N
- SMILES
- O[C@@H]1[C@H]([C@H](O)[C@@H](CO)O[C@H]1C1C=CC(C)=C(CC2=CC=C(C3C=CC(F)=CC=3)S2)C=1)O |&1:1,2,3,5,9,r|
- CAS Datenbank
- 842133-18-0
Canagliflozin Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
In March 2013, the US FDA approved canagliflozin (JNJ-28431754;
TA-7284) for the treatment of type 2 diabetes in adults.
Canagliflozin is the first US-approved sodium-glucose co-transporter (SGLT) inhibitor for the treatment of type 2 diabetes. Inhibition of renal SGLT suppresses glucose reabsorption, which permits glucose excretion into urine and reduction of hyperglycemia. Canagliflozin was discovered through structural modifications of phlorizin, a known inhibitor of renal glucose reabsorption. Early modifications of OH groups on the glucose moiety were insufficient to adequately impair hydrolysis by intestinal β-glucosidase. Introduction of the C-glucoside moiety, as in the clinical candidate dapagliflozin, afforded sufficient resistance to hydrolysis. Finally, incorporation of the thiophene moiety in canagliflozin provided improved potency for hSGLT2 (exclusive to kidney), IC
50=2.2 nM, while offering significant selectivity over hSGLT1 (in kidney and heart), IC
50=910 nM. Hyperglycemic, high-fat (HF) diet fedmice (KKstrain) that received a single 3 mg/kg oral dose of canagliflozin had a 48% reduction in blood glucose levels after 6 h versus
vehicle-treatedmice. Noteworthy in themultistep synthesis of canagliflozin
is the stereoselective formation of the β-C-glucoside which is accomplished by coupling of the aryllithiumaglycone with 2,3,4,6-tetra-O-trimethylsilyl-β-Dgluconolactone followed by desilylation and stereoselective reduction with triethylsilane and boron trifluoride etherate.
Chemische Eigenschaften
Pale Yellow Solid
Verwenden
Canagliflozin is a sodium/glucose cotransporter 2 (SGLT2) inhibitor. Canagliflozin has been shown to dose dependently reduce calculated renal threshold for glucose excretion and increase urinary glucose excretion. Canagliflozin is a candidate for the treatment of type 2 diabetes and obesity.
Definition
ChEBI: A C-glycosyl compound that is used (in its hemihydrate form) for treatment of type II diabetes via inhibition of sodium-glucose transport protein subtype 2.
Canagliflozin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Canagliflozin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 461)Lieferanten
- D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, (1S)-
- Cango coluMn net
- TA 7284
- Canagliflozin(TA-7284)
- Canagliflozin, >=98%
- Canagliflozin-D6
- D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl
- Canagliflozin WS
- Canagliflozi
- (1S)-1,5-Anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl]-D-glucitol
- JNJ 24831754ZAE
- JNJ 28431754AAA
- Canagliflozin
- CS-183
- Canagliflozin USP/EP/BP
- (2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)thiophen-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
- Canagliflozin (JNJ 28431754)
- CanagliflozinQ: What is
Canagliflozin Q: What is the CAS Number of
Canagliflozin Q: What is the storage condition of
Canagliflozin Q: What are the applications of
Canagliflozin
- Canaglifozion
- (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
- Canaglifozin
- (1S)-1,5-anhydro-1-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4 -methylphenyl]-D-glucitol
- JNJ 28431754
- Cagliflozin
- Invokana
- Kangglijing
- Calaglizin
- JNJ 24831754
- JNJ24831754
- JNJ-24831754
- JNJ24831754AAA
- (2R,4S,5S,6R)-2-butyl-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-4,5-dihydroxy-6-(hydroxymethyl)dihydro-2H-pyran-3(4H)-one
- Canagliflozin Impurity 112
- Canagliflozin Impurity 93
- 842133-18-0
- 842133--86-0
- C24H25FO5S
- Aromatics
- Heterocycles
- Inhibitors
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Sulfur & Selenium Compounds
- Other APIs
- Stable Isotopes
- API
