Betrixaban

Betrixaban (trade name Bevyxxa) is an oral anticoagulant drug which acts as a direct factor Xa inhibitor.^[1] Betrixaban is FDA approved for venous thrombosis prevention in adults hospitalized for an acute illness who are at risk for thromboembolic complications.^[2] Compared to other directly acting oral anticoagulants betrixaban has relatively low renal excretion and is not metabolized by CYP3A4.^[3]

Betrixaban

Clinical data
Trade names	Bevyxxa
Other names	PRT054021, PRT064445
AHFS/Drugs.com	bevyxxa
Routes of administration	By mouth
ATC code	B01AF04 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Protein binding	60%
Elimination half-life	19–27 hrs
Duration of action	≥72 hrs
Excretion	85% feces, 11% urine
Identifiers
IUPAC name N-(5-Chloropyridin-2-yl)-2-([4-(N,N-dimethylcarbamimidoyl)benzoyl]amino)-5-methoxybenzamide
CAS Number	330942-05-7 N
PubChem CID	10275777
DrugBank	DB12364 Y
ChemSpider	18981107 Y
UNII	74RWP7W0J9
KEGG	D08873
ChEBI	CHEBI:140421
ChEMBL	ChEMBL512351 Y
CompTox Dashboard (EPA)	DTXSID10954727
ECHA InfoCard	100.207.746
Chemical and physical data
Formula	C23H22ClN5O3
Molar mass	451.91 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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) Y Key:XHOLNRLADUSQLD-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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.^[4]

The drug has undergone clinical trials for prevention of embolism after knee surgery^[5] and for prevention of stroke following non-valvular atrial fibrillation.^[6][7] Betrixaban was also studied in a large phase III clinical trial for extended duration thromboprophylaxis in acute ill patients.^[8] Previously apixaban and rivaroxaban have failed to show positive risk/benefit ratio in this indication compared to enoxaparin.^{[9][10][non-primary source needed]} 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.^[11] Based on these results betrixaban was approved by FDA on June 23, 2017, becoming the first DOAC approved for extended prophylaxis in hospitalized patients.^[12]

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.^[13]

See also

• Edoxaban
• Enoxaparin