Betrixaban

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Chemical compound

title: "Betrixaban" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["direct-xa-inhibitors", "2-aminopyridines", "amides", "amidines", "benzene-derivatives", "chloropyridines", "methoxy-compounds"] description: "Chemical compound" topic_path: "general/direct-xa-inhibitors" source: "https://en.wikipedia.org/wiki/Betrixaban" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461744356 | IUPAC_name = N-(5-Chloropyridin-2-yl)-2-([4-(N,N-dimethylcarbamimidoyl)benzoyl]amino)-5-methoxybenzamide | image = Betrixaban.svg | image_class = skin-invert-image | width = 220

| tradename = Bevyxxa | Drugs.com = | synonyms = PRT054021, PRT064445 | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = Rx-only | legal_status = | routes_of_administration = By mouth

| bioavailability = | protein_bound = 60% | metabolism = | elimination_half-life = 19–27 hrs | duration_of_action = ≥72 hrs | excretion = 85% feces, 11% urine

| CAS_number_Ref = | CAS_number = 330942-05-7 | ATC_prefix = B01 | ATC_suffix = AF04 | ChEMBL_Ref = | ChEMBL = 512351 | ChEBI = 140421 | PubChem = 10275777 | DrugBank_Ref = | DrugBank = DB12364 | UNII_Ref = | UNII = 74RWP7W0J9 | KEGG = D08873 | ChemSpiderID_Ref = | ChemSpiderID = 18981107

| C=23 | H=22 | Cl=1 | N=5 | O=3 | smiles = CN(C)C(=N)C1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)OC)C(=O)NC3=NC=C(C=C3)Cl | StdInChI_Ref = | StdInChI = 1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31) | StdInChIKey_Ref = | StdInChIKey = XHOLNRLADUSQLD-UHFFFAOYSA-N

Betrixaban (trade name Bevyxxa) is an oral anticoagulant drug which acts as a direct factor Xa inhibitor. Betrixaban is FDA approved for venous thrombosis prevention in adults hospitalized for an acute illness who are at risk for thromboembolic complications. Compared to other directly acting oral anticoagulants betrixaban has relatively low renal excretion and is not metabolized by CYP3A4.

History

Betrixaban was originally developed by Millennium Pharmaceuticals. Portola Pharmaceuticals acquired rights for betrixaban in 2004 and co-developed it with Merck. In 2011 Merck discontinued joint development.

The drug has undergone clinical trials for prevention of embolism after knee surgery and for prevention of stroke following non-valvular atrial fibrillation. Betrixaban was also studied in a large phase III clinical trial for extended duration thromboprophylaxis in acute ill patients. Previously apixaban and rivaroxaban have failed to show positive risk/benefit ratio in this indication compared to enoxaparin. APEX trial compared betrixaban with enoxaparin and included 7513 patients. Lower rate of VTE events was found in betrixaban arm with no increase in major bleedings compared to enoxaparin. Based on these results betrixaban was approved by FDA on June 23, 2017, becoming the first DOAC approved for extended prophylaxis in hospitalized patients.

Betrixaban has been also reviewed by EMA but didn't receive marketing approval in EU mainly due to concerns of increased bleeding risk and absence of reversal agent.

References

References

  1. (2009). "Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development". Clinical Pharmacokinetics.
  2. (May 2025). "Approved Drugs - FDA approved betrixaban (BEVYXXA, Portola) for the prophylaxis of venous thromboembolism (VTE) in adult patients". U.S. Food and Drug Administration.
  3. (May 2018). "Pharmacological properties of betrixaban". European Heart Journal Supplements.
  4. (24 March 2011). "Merck Abandons Development of Factor Xa Inhibitor Betrixaban". CardioBrief.
  5. (January 2009). "A randomized evaluation of betrixaban, an oral factor Xa inhibitor, for prevention of thromboembolic events after total knee replacement (EXPERT)". Thrombosis and Haemostasis.
  6. (July 2010). "Oral factor Xa inhibitors for the prevention of stroke in atrial fibrillation". Current Opinion in Cardiology.
  7. (July 2009). "New anticoagulants for atrial fibrillation". Seminars in Thrombosis and Hemostasis.
  8. (March 2014). "The design and rationale for the Acute Medically Ill Venous Thromboembolism Prevention with Extended Duration Betrixaban (APEX) study". American Heart Journal.
  9. (February 2013). "Rivaroxaban for thromboprophylaxis in acutely ill medical patients". The New England Journal of Medicine.
  10. (December 2011). "Apixaban versus enoxaparin for thromboprophylaxis in medically ill patients". The New England Journal of Medicine.
  11. (August 2016). "Extended Thromboprophylaxis with Betrixaban in Acutely Ill Medical Patients". The New England Journal of Medicine.
  12. (May 2025). "FDA approved betrixaban (BEVYXXA, Portola) for the prophylaxis of venous thromboembolism (VTE) in adult patients".
  13. (27 July 2018). "Refusal of the marketing authorisation for Dexxience (betrixaban): Outcome of re-examination". European Medicines Agency.

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direct-xa-inhibitors2-aminopyridinesamidesamidinesbenzene-derivativeschloropyridinesmethoxy-compounds