Betrixaban

Betrixaban

Systematic (IUPAC) name
N-(5-chloropyridin-2-yl)-2-([4-(N,N-dimethylcarbamimidoyl)benzoyl]amino)-5-methoxybenzamide
Clinical data
Legal status	Being evaluated in the global Phase 3 trial (APEX)
Identifiers
CAS Number	330942-05-7
ATC code	none
PubChem	CID 10275777
ChemSpider	18981107
UNII	74RWP7W0J9
ChEMBL	CHEMBL512351
Chemical data
Formula	C23H22ClN5O3
Molar mass	451.905 g/mol
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) Key:XHOLNRLADUSQLD-UHFFFAOYSA-N
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Betrixaban (INN, codenamed PRT-054,021) is an anticoagulant drug which acts as a direct factor Xa inhibitor.^[1] It is potent, orally active and highly selective for factor Xa, being selected from a group of similar compounds for its low hERG affinity.^[2] Betrixaban has undergone human clinical trials for prevention of embolism after knee surgery,^[3] and prevention of stroke following atrial fibrillation,^[4] with promising results.^[5] Betrixaban is currently being studied in a human clinical trial for extended duration thromboprophylaxis to prevent venous thromboembolism in acute medically ill patients.^[6] Joint development with Portola was discontinued in 2011 by Merck.^[7] Betrixaban is now being developed by Portola Pharmaceuticals.

See also

• Rivaroxaban
• Apixaban

References

1. Eriksson BI, Quinlan DJ, Weitz JI (2009). "Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development". Clinical Pharmacokinetics 48 (1): 1–22. doi:10.2165/0003088-200948010-00001. PMID 19071881.
2. Zhang P, Huang W, Wang L, Bao L, Jia ZJ, Bauer SM, Goldman EA, Probst GD, Song Y, Su T, Fan J, Wu Y, Li W, Woolfrey J, Sinha U, Wong PW, Edwards ST, Arfsten AE, Clizbe LA, Kanter J, Pandey A, Park G, Hutchaleelaha A, Lambing JL, Hollenbach SJ, Scarborough RM, Zhu BY (April 2009). "Discovery of betrixaban (PRT054021), N-(5-chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide, a highly potent, selective, and orally efficacious factor Xa inhibitor". Bioorganic & Medicinal Chemistry Letters 19 (8): 2179–85. doi:10.1016/j.bmcl.2009.02.111. PMID 19297154.
3. Turpie AG, Bauer KA, Davidson BL, Fisher WD, Gent M, Huo MH, Sinha U, Gretler DD (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 101 (1): 68–76. doi:10.1160/th08-07-0460. PMID 19132191.
4. Piccini, J. P.; Lopes, R. D.; Mahaffey, K. W. (2010). "Oral factor Xa inhibitors for the prevention of stroke in atrial fibrillation". Current Opinion in Cardiology 25 (4): 312–20. doi:10.1097/HCO.0b013e32833a524f. PMID 20520539.
5. Sobieraj-Teague, M.; O’donnell, M.; Eikelboom, J. (2009). "New Anticoagulants for Atrial Fibrillation". Seminars in Thrombosis and Hemostasis 35 (5): 515–24. doi:10.1055/s-0029-1234147. PMID 19739042.
6. Cohen, Alexander T.; Harrington, Robert; Goldhaber, Samuel Z.; Hull, Russell; Gibson, C. Michael; Hernandez, Adrian F.; Kitt, Michael M.; Lorenz, Todd J. (2014-01-01). "The design and rationale for the Acute Medically Ill Venous Thromboembolism Prevention with Extended Duration Betrixaban (APEX) study". American Heart Journal 167 (3). doi:10.1016/j.ahj.2013.11.006.
7. Husten, Harry. "Merck Abandons Development of Factor Xa Inhibitor Betrixaban". CardioBrief. Retrieved 11 April 2014.