Rivaroxaban

{{drugbox | | IUPAC_name = 5-chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)
phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide | image = Rivaroxaban structure.svg | width = 200 | CAS_number = 366789-02-8 | ATC_prefix = B01 | ATC_suffix = AX06 | ATC_supplemental = | PubChem = 6433119 | DrugBank = | C=19 | H=18 | Cl=1 | N=3 | O=5 | S=1 | molecular_weight = 435.882 g/mol | smiles = O=C1COCCN1c3ccc(cc3)N2CC(OC2=O)CNC(=O)c(cc4)sc4Cl | bioavailability = 60 to 80% | metabolism = | elimination_half-life = 5.7 to 9.2 hours, increases with age and renal impairment | excretion = Renal (66%) and biliary (28%) | pregnancy_category = | legal_status = | routes_of_administration = oral }}

Rivaroxaban (BAY 59-7939) is an oral anticoagulant under development by Bayer; it will be marketed as Xarelto. It acts by inhibiting the active form of coagulation factor X (factor Xa).

Development

Rivaroxaban is an oxazolidinone derivative optimised for binding with factor Xa. If marketed, it will be a joint product by Bayer and Ortho-McNeil Pharmaceutical.

Uses

Expected

Due to the decreased need for monitoring, rivaroxaban is likely to be used to replace warfarin for a number of indications, such as atrial fibrillation.

Trial results

In phase IIb trials it was effective in reducing thromboembolic complications (deep vein thrombosis and pulmonary embolism) after orthopedic surgery and it is under investigation for the prevention of DVT and PE and for anticoagulation in atrial fibrillation. Advantages are the oral administration (a benefit over low molecular weight heparins, which require subcutaneous injections) and no need for monitoring (an advantage over warfarin). In studies, dosages of 2.5-10 mg once or twice daily were used.

Bayer-sponsored phase 3 clinical trials showed that once-daily rivaroxaban achieved superior efficacy and similar safety in the prevention of venous thromboembolism (VTE) in patients undergoing knee replacement or hip arthroplasty surgery in comparison with enoxaparin, a LMWH.

Related drugs

Ximelagatran, a direct thrombin inhibitor, was not marketed further due to its potential side-effects; the related compound dabigatran was recently approved in the European Union. Together with rivaroxaban, the related factor Xa-inhibitor apixaban (Bristol-Myers-Squibb) and LY517717 (Lilly) are under development as non-monitored antithrombotic drugs.

References

External links

• Xarelto.com