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Rivaroxaban (Molecule of the Month for May 2017)

Xarelto



Rivaroxaban is an anticoagulant medication (blood thinner), which is taken by mouth. It is commonly used to prevent blood clots. It is the first available active direct factor Xa inhibitor which is taken by mouth. It allows predictable anticoagulation and dose adjustments and routine coagulation monitoring as well as dietary restrictions are not needed.

In those with non-valvular atrial fibrillation it appears to be as effective as warfarin in preventing nonhemorrhagic strokes and embolic events. Rivaroxaban is associated with lower rates of serious and fatal bleeding events than warfarin though rivaroxaban is associated with higher rates of bleeding in the gastrointestinal tract. The most serious adverse effect is bleeding, including severe internal bleeding. Rivaroxaban is associated with lower rates of serious and fatal bleeding events than warfarin but is associated with higher rates of bleeding in the gastrointestinal tract. There is currently no antidote for rivaroxaban (unlike warfarin, the action of which can be reversed with vitamin K or prothrombin complex concentrate), meaning that serious bleeding may be difficult to manage. Using rivaroxaban rather than warfarin costs 70 times more.

Rivaroxaban inhibits both free Factor Xa and Factor Xa bound in the prothrombinase complex. It is a highly selective direct Factor Xa inhibitor with oral bioavailability and rapid onset of action. Inhibition of Factor Xa interrupts the intrinsic and extrinsic pathway of the blood coagulation cascade, inhibiting both thrombin formation and development of thrombi.

Formal Chemical Name (IUPAC)
(S)-5-chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide

References

https://en.wikipedia.org/wiki/Rivaroxaban

Picture of Rivaroxaban 3D model

click on the picture of  Rivaroxaban above to interact
with the 3D model of the
Rivaroxaban structure
(this will open a new browser window)

Picture of Rivaroxaban

C19H18ClN3O5S



Update by Karl Harrison
(Molecule of the Month for May 2017 )

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