|
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 | C19H18ClN3O5S
|
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).
Additional recommended knowledge
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.
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 |
---|
|