Betrixaban

Betrixaban
Systematic (IUPAC) name

N-(5-chloropyridin-2-yl)-2-([4-(N,N-dimethylcarbamimidoyl)benzoyl]amino)-5-methoxybenzamide
Clinical data
Identifiers
CAS Registry Number	330942-05-7^N
ATC code	None
PubChem	CID 10275777
ChemSpider	18981107^Y
UNII	74RWP7W0J9^Y
ChEMBL	CHEMBL512351^Y
Chemical data
Formula	C₂₃H₂₂Cl N₅O₃
Molecular 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) ^Y Key:XHOLNRLADUSQLD-UHFFFAOYSA-N ^Y
N (what is this?) (verify)

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]Joint development with Portola was discontinued in 2011 by Merck.^[6]

References

↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ Husten, Harry. "Merck Abandons Development of Factor Xa Inhibitor Betrixaban". CardioBrief. Retrieved 11 April 2014.

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Tirofiban Roxifiban Orbofiban

ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor

Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal

Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+Aspirin) Picotamide Receptor antagonists Terutroban^†

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low molecular weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin^‡ Oligosaccharides Fondaparinux Idraparinux^§ Heparinoids Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors	Xabans Apixaban Betrixaban^§ Darexaban^§ Edoxaban Otamixaban^§ Rivaroxaban

Direct thrombin (IIa) inhibitors

Bivalent: Hirudin
- Bivalirudin
- Desirudin
- Lepirudin
Univalent: Argatroban
Dabigatran
Melagatran^‡
Ximelagatran^‡

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Index of cells from bone marrow

Description	Immune system Cells Physiology coagulation proteins granule contents colony-stimulating heme and porphyrin metabolism intermediates

Disease	Red blood cell Monocyte and granulocyte Neoplasms and cancer Histiocytosis Symptoms and signs eponymous Blood tests findings

Treatment	Transfusion Drugs thrombosis bleeding other

Betrixaban

See also

References