Rivaroxaban

drugbox
IUPAC_name = 5-chloro-"N"-{ [(5"S")-2-oxo-3- [4-(3-oxomorpholin-4-yl)
phenyl] oxazolidin-5-yl] methyl} thiophene-2-carboxamide

---

width = 200
CAS_number = 366789-02-8
ATC_prefix = B01
ATC_suffix = AX06
ATC_supplemental = [cite web |url=http://www.whocc.no/atcddd/new_atc_ddd.html#ATCDDD_FINAL |title=ATC/DDD Classification (FINAL): New ATC 5th level codes |date=August 27, 2008 |author=WHO International Working Group for Drug Statistics Methodology |publisher=WHO Collaborating Centre for Drug Statistics Methodology |accessdate=2008-09-05]
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. [cite journal |author=Roehrig S, Straub A, Pohlmann J, "et al" |title=Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl] -1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor |journal=J. Med. Chem. |volume=48 |issue=19 |pages=5900–8 |year=2005 |pmid=16161994 |doi=10.1021/jm050101d] If marketed, it will be a joint product by Bayer and Ortho-McNeil Pharmaceutical. [cite web|url=http://www.pharmabiz.com/article/detnews.asp?SecArch=&articleid=30056&sectionid=14|title=Bayer, Ortho-McNeil to co-develop key thrombosis drug|author=Pharmabiz.com|accessdate=2007-12-03]

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.ClinicalTrials|NCT00403767]

Trial results

In phase IIb trials it was effective in reducing thromboembolic complications (deep vein thrombosis and pulmonary embolism) after orthopedic surgerycite journal |author=Eriksson BI, Borris L, Dahl OE, "et al" |title=Oral, direct Factor Xa inhibition with BAY 59-7939 for the prevention of venous thromboembolism after total hip replacement |journal=J. Thromb. Haemost. |volume=4 |issue=1 |pages=121–8 |year=2006 |pmid=16409461 |doi=10.1111/j.1538-7836.2005.01657.x|url=http://www.blackwell-synergy.com/doi/full/10.1111/j.1538-7836.2005.01657.x] 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. [cite journal | author=Eriksson BI, Borris LC, Friedman RJ "et al" | title=Rivaroxaban versus enoxaparin for thromboprophylaxis after hip arthroplasty | journal= N. Engl. J. Med. | year=2008 | volume=358 | pages=2765–75 | doi=10.1056/NEJMoa0800374] [cite journal | author=Lassen MR, Ageno W, Borris LC "et al" | title=Rivaroxaban versus enoxaparin for thromboprophylaxis after total knee arthroplasty | journal=N. Engl. J. Med. | year=2008 | volume=358 | pages=2776–2786 | doi=10.1056/NEJMoa076016]

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. [cite journal |author=Hampton T |title=New oral anticoagulants show promise. |journal=JAMA |volume=295 |issue=7 |pages=743–4 |year=2006 |pmid=16478891 |doi=10.1001/jama.295.7.743]

References

External links

* [http://www.xarelto.com Xarelto.com]