Case History. Eliquis™ (Apixaban), a Potent and Selective Inhibitor of Coagulation Factor Xa for the Prevention and Treatment of Thrombotic Diseases

Annual Reports in Medicinal Chemistry

Volumn 47, Issue , 2012, Pages 123-141

  Pinto, Donald J P ^a   Wong, Pancras C ^a   Knabb, Robert M ^a   Wexler, Ruth R ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Anticoagulant; Apixaban; APPRAISE; ARISTOTLE; AVERROES; Factor Xa

Indexed keywords

EID: 84866754576     PISSN: 00657743     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-396492-2.00009-6     Document Type: Chapter

References (43)

1. Soff G.A. Arterioscler. Thromb. Vasc. Biol. 2012, 32:569.
2. Mann K.G., Butenas S., Brummel K. Arterioscler. Thromb. Vasc. Biol. 2003, 23:17.
3. McKenzie C.R., Abendschein D.R., Eisenberg P.R. Arterioscler. Thromb. Vasc. Biol. 1996, 16:1285.
4. Harker L.A., Hanson S.R., Kelly A.B. Thromb. Haemost. 1995, 74:464.
5. Morishima Y., Tanabe K., Terada Y., Hara T., Kunitada S. Thromb. Haemost. 1997, 78:1366.
6. Sato K., Kawasaki T., Taniuchi Y., Hirayama F., Koshio H., Matsumoto Y. Eur. J. Pharmacol. 1997, 339:141.
7. Wong P.C., Crain E.J., Watson C.A., Zaspel A.M., Wright M.R., Lam P.Y., Pinto D.J., Wexler R.R., Knabb R.M. J. Pharmacol. Exp. Ther. 2002, 303:993.
8. Wong P.C., Crain E.J., Watson C.A., Xin B. J. Thromb. Haemost. 2009, 7:1313.
9. Tidwell R.R., Webster W.P., Shaver S.R., Geratz J.D. Thromb. Res. 1980, 19:339.
10. Sturzebecher J., Markwardt F., Walsmann P. Thromb. Res. 1976, 9:637.
11. Nagahara T., Yokoyama Y., Inamura K., Katakura S., Komoriya S., Yamaguchi H., Hara T., Iwamoto M. J. Med. Chem. 1994, 37:1200.
12. Maduskuie T.P., McNamara K.J., Ru Y., Knabb R.M., Stouten P.F. J. Med. Chem. 1998, 41:53.
13. Quan M.L., Wexler R.R. Curr. Top. Med. Chem. 2001, 1:137.
14. Quan M.L., Pruitt J.R., Ellis C.D., Liauw A.Y., Galemmo R.A., Stouten P.F.W., Wityak J., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. Bioorg. Med. Chem. Lett. 1997, 7:2813.
15. Quan M.L., Liauw A.Y., Ellis C.D., Pruitt J.R., Carini D.J., Bostrom L.L., Huang P.P., Harrison K., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. J. Med. Chem. 1999, 42:2752.
16. Quan M.L., Ellis C.D., Liauw A.Y., Alexander R.S., Knabb R.M., Lam G., Wright M.R., Wong P.C., Wexler R.R. J. Med. Chem. 1999, 42:2760.
17. Pruitt J.R., Pinto D.J., Estrella M.J., Bostrom L.L., Knabb R.M., Wong P.C., Wright M.R., Wexler R.R. Bioorg. Med. Chem. Lett. 2000, 10:685.
18. Pinto D.J.P., Orwat M.J., Wang S., Fevig J.M., Quan M.L., Amparo E., Cacciola J., Rossi K.A., Alexander R.S., Smallwood A.M., Luettgen J.M., Liang L., Aungst B.J., Wright M.R., Knabb R.M., Wong P.C., Wexler R.R., Lam P.Y.S. J. Med. Chem. 2001, 44:566.
19. Fevig J.M., Pinto D.J., Han Q., Quan M.L., Pruitt J.R., Jacobson I.C., Galemmo R.A., Wang S., Orwat M.J., Bostrom L.L., Knabb R.M., Wong P.C., Lam P.Y.S., Wexler R.R. Bioorg. Med. Chem. Lett. 2001, 11:641.
20. Pinto D.J.P., Smallheer J.M., Cheney D.L., Knabb R.M., Wexler R.R. J. Med. Chem. 2010, 53:6243.
21. Pruitt J.R., Pinto D.J.P., Galemmo R.A., Alexander R.S., Rossi K.A., Wells B.L., Drummond S., Bostrom L.L., Burdick D., Bruckner R., Chen H., Smallwood A., Wong P.C., Wright M.R., Bai S., Luettgen J.M., Knabb R.M., Lam P.Y.S., Wexler R.R. J. Med. Chem. 2003, 46:5298.
22. Lam P.Y.S., Clark C.G., Li R., Pinto D.J.P., Orwat M.J., Galemmo R.A., Fevig J.M., Teleha C.A., Alexander R.S., Smallwood A.M., Rossi K.A., Wright M.R., Bai S.A., He K., Luettgen J.M., Wong P.C., Knabb R.M., Wexler R.R. J. Med. Chem. 2003, 46:4405.
23. Qiao J.X., Lam P.Y.S. Synthesis 2011, 6:829.
24. Qua M.L., Lam P.Y.S., Han Q., Pinto D.J.P., He M.Y., Li R., Ellis C.D., Clark C.G., Teleha C.A., Sun J.H., Alexander R.S., Bai S., Luettgen J.M., Knabb R.M., Wong P.C., Wexler R.R. J. Med. Chem. 2005, 48:1729.
25. Wong P.C., Crain E.J., Watson C.A., Wexler R.R., Lam P.Y.S., Quan M.L., Knabb R.M. J. Thromb. Thrombolysis 2007, 24:43.
26. Varnes J.G., Wacker D.A., Jacobson I.C., Quan M.L., Ellis C.D., Rossi K.A., He M.Y., Luettgen J.M., Knabb R.M., Bai S., He K., Lam P.Y.S., Wexler R.R. Bioorg. Med. Chem. Lett. 2007, 17:6481.
27. Varnes J.G., Wacker D.A., Pinto D.J.P., Orwat M.J., Theroff J.P., Wells B., Galemmo R.A., Luettgen J.M., Knabb R.M., Bai S., He K., Lam P.Y.S., Wexler R.R. Bioorg. Med. Chem. Lett. 2008, 18:749.
28. Fevig J.M., Cacciola J., Buriak J., Rossi K.A., Knabb R.M., Luettgen J.M., Wong P.C., Bai S.A., Wexler R.R., Lam P.Y.S. Bioorg. Med. Chem. Lett. 2006, 16:3755.
29. Li Y.L., Fevig J.M., Cacciola J., Buriak J., Rossi K.A., Jona J., Knabb R.M., Luettgen J.M., Wong P.C., Bai S.A., Wexler R.R., Lam P.Y.S. Bioorg. Med. Chem. Lett. 2006, 16:5176.
30. Pinto D.J.P., Orwat M.J., Quan M.L., Han Q., Galemmo R.A., Amparo E., Wells B., Ellis C.D., He M.Y., Alexander R.S., Rossi K.A., Smallwood A., Wong P.C., Luettgen J.M., Rendina A.R., Knabb R.M., Mersinger L., Kettner C., Bai S., He K., Wexler R.R., Lam P.Y.S. Bioorg. Med. Chem. Lett. 2006, 16:4141.
31. Pinto D.J.P., Orwat M.J., Koch S., Rossi K.A., Alexander R.S., Smallwood A., Wong P.C., Rendina A.R., Luettgen J.M., Knabb R.M., He K., Xin B., Wexler R.R., Lam P.Y.S. J. Med. Chem. 2007, 50:5339.
32. He K., Luettgen J.M., Zhang D., He B., Grace J.E., Xin B., Pinto D.J.P., Wong P.C., Knabb R.M., Lam P.Y.S., Wexler R.R., Grossman S. Eur. J. Drug Metab. Pharmacokinet. 2011, 36:129.
33. Luettgen J.M., Knabb R.M., He K., Pinto D.J.P., Rendina A.R. J. Enzyme Inhib. Med. Chem. 2011, 26:514.
34. Wong P.C., Pinto D.J.P., Zhang D. J. Thromb. Thrombolysis 2011, 31:478.
35. PrELIQUIS (apixaban) Product Monograph [online]. Accessed Feb 6, 2012. http://www.pfizer.ca/en/our_products/products/monograph/313.
36. Lassen M.R., Davidson B.L., Gallus A., Pineo G., Ansell J., Deitchman D. J. Thromb. Haemost. 2007, 5:2368.
37. Lassen M.R., Raskob G.E., Gallus A., Pineo G., Chen D., Hornick P. ADVANCE-2 investigators. Lancet 2010, 375:807.
38. Lassen M.R., Gallus A., Raskob G.E., Pineo G., Chen D., Ramirez L.M. ADVANCE-3 Investigators. N. Engl. J. Med. 2010, 363:2487.
39. Lassen M.R., Raskob G.E., Gallus A., Pineo G., Chen D., Portman R.J. N. Engl. J. Med. 2009, 361:594.
40. Buller H., Deitchman D., Prins M., Segers A., Botticelli Investigators, Writing Committee. J.Thromb. Haemost. 2008, 6:1313.
41. Alexander J.H., Becker R.C., Bhatt D.L., Cools F., Crea F., Dellborg M., Fox K.A., Goodman S.G., Harrington R.A., Huber K., Husted S., Lewis B.S., Lopez-Sendon J., Mohan P., Montalescot G., Ruda M., Ruzyllo W., Verheugt F., Wallentin L., APPRAISE Steering Committee and Investigators. Circulation 2009, 119:2877.
42. Alexander J.H., Lopes R.D., James S., Kilaru R., He Y., Mohan P., Bhatt D.L., Goodman S., Verheugt F.W., Flather M., Huber K., Liaw D., Husted S.E., Lopez-Sendon J., De Caterina R., Jansky P., Darius H., Vinereanu D., Cornel J.H., Cools F., Atar D., Leiva-Pons J.L., Keltai M., Ogawa H., Pais P., Parkhomenko A., Ruzyllo W., Diaz R., White H., Ruda M., Geraldes M., Lawrence J., Harrington R.A., Wallentin L., APPRAISE-2 Investigators. N. Engl. J. Med. 2011, 365:699.
43. Connolly S.J., Eikelboom J., Joyner C., Diener H.C., Hart R., Golitsyn S., Flaker G., Avezum A., Hohnloser S.H., Diaz R., Talajic M., Zhu J., Pais P., Budaj A., Parkhomenko A., Jansky P., Commerford P., Tan R.S., Sim K.H., Lewis B.S., Van Mieghem W., Lip G.Y., Kim J.H., Lanas-Zanetti F., Gonzalez-Hermosillo A., Dans A.L., Munawar M., O'Donnell M., Lawrence J., Lewis G., Afzal R., Yusuf S., AVERROES Steering Committee and Investigators. N. Engl. J. Med. 2011, 364:806.