Basic information Safety Supplier Related

5-R-Rivaroxaban

Basic information Safety Supplier Related

5-R-Rivaroxaban Basic information

Product Name:
5-R-Rivaroxaban
Synonyms:
  • 5-R-Rivaroxaban
  • 5-Chloro-N-[[(5R)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide
  • R-Rivaroxaban
  • (R)-5-chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide
  • ent-Rivaroxaban
  • Rivaroxaban R-Isomer Impurity
  • (R)-Rivaroxaban, ent-Rivaroxaban
  • Rivaroxaban R-Isomer
CAS:
865479-71-6
MF:
C19H18ClN3O5S
MW:
435.88
Mol File:
865479-71-6.mol
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5-R-Rivaroxaban Chemical Properties

Melting point:
>227°C (dec.)
Boiling point:
732.6±60.0 °C(Predicted)
Density 
1.460
storage temp. 
Refrigerator
solubility 
Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly, Sonicated), Methanol
form 
Solid
pka
13.36±0.46(Predicted)
color 
White to Off-White
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5-R-Rivaroxaban Usage And Synthesis

Uses

ent-Rivaroxaban is the R-isomer of Rivaroxaban (R538000), which is a novel antithrombotic agent. A highly potent and selective, direct FXa inhibitor.

Biological Activity

5-r-rivaroxaban is a selective inhibitor of human factor xa with ic50 value of 0.7 nmol/l [1].factor xa is a serine endopeptidase enzyme and plays an important role in the convergence point of the intrinsic and extrinsic pathways in blood coagulation system [2].5-r-rivaroxaban is an oral, direct factor xa inhibitor and the inhibition is species-dependent. when tested with purified factoe xa from human or rabbit, 5-r-rivaroxaban showed similar affinity with ic50 value of 0.7 nmol/l and 0.8 nmol/l, respectively, while had a ic50 value as low as 3.4 nmol/l when tested with rat factor xa [1].pre-treated anaesthetised rat model with intravenous 5-r-rivaroxaban at a dose of 2 mg/kg, and after bleeding initiated intravenous treated with rfviia (100/400 μg/kg), pcc (25/50 u/kg) or apcc (50/100 u/kg), the result showed that 5-r-rivaroxaban pre-treatment significantly shorten bleeding time and clotting time compared with 5-r-rivaroxaban alone treated group [2]. similar results were obtained when tested with rabbit model [1].it has been reported that 5-r-rivaroxaban is a promising drug for atrial fibrillation, venous thromboembolism or thromboembolic disorders in clinic [3] [4] [1].

References

[1]. perzborn, e., et al., rivaroxaban: a new oral factor xa inhibitor. arterioscler thromb vasc biol, 2010. 30(3): p. 376-81.
[2]. perzborn, e., et al., reversal of rivaroxaban anticoagulation by haemostatic agents in rats and primates. thromb haemost, 2013. 110(1): p. 162-72.
[3]. beyer-westendorf, j., et al., efficacy and safety of rivaroxaban or fondaparinux thromboprophylaxis in major orthopedic surgery: findings from the ortho-tep registry. j thromb haemost, 2012. 10(10): p. 2045-52.
[4]. palareti, g., et al., clinical management of rivaroxaban-treated patients. expert opin pharmacother, 2013. 14(5): p. 655-67.

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