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Rivaroxaban


Rivaroxaban
Systematic (IUPAC) name
5-chloro-N-[[2-oxo-3-[4-(3-oxomorpholin-4-yl) phenyl]oxazolidin-5-yl]methyl] thiophene-2-carboxamide
Identifiers
CAS number	366789-02-8
ATC code	?
PubChem	6433119
Chemical data
Formula	C₁₉H₁₈Cl N₃O₅S
Mol. mass	435.882
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	5.7-9.2
Excretion	?
Therapeutic considerations
Pregnancy cat.	??
Legal status	??
Routes	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).

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1 Development
2 Uses
- 2.1 Expected
- 2.2 Trial results
3 Related drugs
4 References

Development

Rivaroxaban is an oxazolidinone derivative optimised for binding with factor Xa.^[1] If marketed, it will be a joint product by Bayer and Ortho-McNeil Pharmaceutical.^[2]

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.^[3]

Trial results

In phase IIb trials it was effective in reducing thromboembolic complications (deep vein thrombosis and pulmonary embolism) after orthopedic surgery^[4] and it is under investigation for the treatment of DVT and PE and for anticoagulation in atrial fibrillation.^[3] 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.^[4]

On July 8, 2007, Bayer sponsored Phase 3 clinical trial data showing once-daily rivaroxaban achieved superior efficacy in the prevention of venous thromboembolism (VTE) in patients undergoing knee replacement surgery in comparison with enoxaparin, a LMWH.^[5]

Related drugs

Ximelagatran, a direct thrombin inhibitor, was not marketed further due to its potential side-effects; the related compound dabigatran is undergoing studies. Together with rivaroxaban, the related factor Xa-inhibitor apixaban (Bristol-Myers-Squibb) and LY517717 (Lilly) are under development as non-monitored antithrombotic drugs.^[6]

References

^ Roehrig S, Straub A, Pohlmann J, et al (2005). "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". J. Med. Chem. 48 (19): 5900–8. doi:10.1021/jm050101d. PMID 16161994.
^ Pharmabiz.com. Bayer, Ortho-McNeil to co-develop key thrombosis drug. Retrieved on 2007-12-03.
^ ^a ^b Clinical trial NCT00403767
^ ^a ^b Eriksson BI, Borris L, Dahl OE, et al (2006). "Oral, direct Factor Xa inhibition with BAY 59-7939 for the prevention of venous thromboembolism after total hip replacement". J. Thromb. Haemost. 4 (1): 121–8. doi:10.1111/j.1538-7836.2005.01657.x. PMID 16409461.
^ The Bayer HealthCare Press Club (2007-07-08). "Phase III Trial Results Show Superiority of Rivaroxaban over Enoxaparin for the Prevention of Venous Thromboembolism in Patients Undergoing Knee Replacement Surgery". Press release. Retrieved on 2007-12-03.
^ Hampton T (2006). "New oral anticoagulants show promise.". JAMA 295 (7): 743–4. doi:10.1001/jama.295.7.743. PMID 16478891.

v • d • e Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)
Vitamin K antagonists	Acenocoumarol • Clorindione • Coumatetralyl • Dicumarol (Dicoumarol) • Diphenadione • Ethyl biscoumacetate • Phenprocoumon • Phenindione • Tioclomarol • Warfarin
Heparin group	Antithrombin III • Danaparoid • Heparin • Sulodexide • low molecular weight heparin (Bemiparin, Dalteparin, Enoxaparin, Nadroparin, Parnaparin, Reviparin, Tinzaparin)
Glycoprotein IIb/IIIa inhibitors	Abciximab • Eptifibatide • Tirofiban
Other platelet aggregation inhibitors	Acetylsalicylic acid/Aspirin • Aloxiprin • Ditazole • Carbasalate calcium • Cloricromen • Dipyridamole • Indobufen • Picotamide • Triflusal • ADP receptor inhibitors (Clopidogrel, Ticlopidine, Prasugrel) • prostaglandin analogue (Beraprost, Prostacyclin, Iloprost, Treprostinil)
Enzymes	plasminogen activators (Alteplase/Reteplase/Tenecteplase, Streptokinase, Urokinase/Saruplase, Anistreplase) • other serine endopeptidases (Ancrod, Drotrecogin alfa/Protein C, Fibrinolysin) • Brinase
Direct thrombin inhibitors	Argatroban • Bivalirudin • Dabigatran • Desirudin • Hirudin • Lepirudin • Melagatran • Ximelagatran
Other antithrombotics	Defibrotide • Dermatan sulfate • Fondaparinux • Rivaroxaban
Non-medicinal	Citrate • EDTA • Oxalate

Categories: Anticoagulants | Thiophenes

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Rivaroxaban". A list of authors is available in Wikipedia.