Structural resemblances and comparisons of the relative pharmacological properties of imatinib and nilotinib

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 19, 2010, Pages 6977-6986

  Manley, Paul W ^a   Stiefl, Nikolaus ^a   Cowan Jacob, Sandra W ^a   Kaufman, Susan ^a   Mestan, Jürgen ^a   Wartmann, Markus ^a   Wiesmann, Marion ^a   Woodman, Richard ^a   Gallagher, Neil ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Adverse events; BCR ABL1; CML; CSF 1R; Imatinib; Nilotinib; Similarity; Tanimoto

Indexed keywords

IMATINIB; NILOTINIB;

ALGORITHM; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CASE REPORT; CHRONIC MYELOID LEUKEMIA; CLINICAL PHARMACOLOGY; DAYLIGHT FINGERPRINT; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TANIMOTO COEFFICIENT;

CELL LINE; CELL SURVIVAL; FUSION PROTEINS, BCR-ABL; HUMANS; LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; PROTEIN KINASE INHIBITORS; PROTEIN-TYROSINE KINASES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956649599     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.026     Document Type: Article

References (65)

1. A.G. Saliner Curr. Comput. Aided Drug Des. 2 2006 105
2. Guideline on aspects of the application of Article 8(1) and (3) of Regulation (EC) No 141/2000: assessing similarity of medicinal products versus authorised orphan medicinal products benefiting from market exclusivity and applying derogations from that market exclusivity. Official J. Eur. Union 2008, C242, 12.
3. Commission Regulation (EC) No 847/2000 of 27 April 2000 laying down the provisions for implementation of the criteria for designation of a medicinal product as an orphan medicinal product and definitions of the concepts 'similar medicinal product' and 'clinical superiority'. Official J. Eur. Union 2000, L103, 5.
4. Communication from the Commission. Guideline on aspects of the application of Article 8(1) and (3) of Regulation (EC) No 141/2000: assessing similarity of medicinal products versus authorised orphan medicinal products benefiting from market exclusivity and applying derogations from that market exclusivity.
5. J.V. Melo, and D.J. Barnes Nat. Rev. Cancer 7 2007 441
6. Zimmermann, J. Pyrimidinderivate und Verfahren zu ihrer Herstellung. Eur. Pat. Appl. 564,409, March 25, 1993.
7. J. Zimmermann, E. Buchdunger, H. Mett, T. Meyer, and N.B. Lydon Bioorg. Med. Chem. Lett. 7 1997 187
8. A. Hochhaus, B. Druker, C. Sawyers, F. Guilhot, C.A. Schiffer, J. Cortes, D.W. Niederwieser, C. Gambacorti, R.M. Stone, J. Goldman, T. Fischer, S.G. O'Brien, J.J. Reiffers, M. Mone, T. Krahnke, M. Talpaz, and H.M. Kantarjian Blood 111 2008 1039
9. J.F. Apperley Lancet Oncol. 8 2007 1018
10. Breitenstein, W.; Furet, P.; Jacob, S.; Manley, P. W. Preparation of pyrimidinylaminobenzamides as inhibitors of protein kinases, in particular tyrosine kinases for treating neoplasm, especially leukemia. PCT Int. Appl. WO 2004005281, Jan 15, 2004.
11. E. Weisberg, P.W. Manley, W. Breitenstein, J. Brüggen, S.W. Cowan-Jacob, A. Ray, B. Huntly, D. Fabbro, G. Fendrich, E. Hall-Meyers, A.L. Kung, J. Mestan, G.Q. Daley, L. Callahan, L. Catley, C. Cavazza, A. Mohammed, D. Neuberg, R.D. Wright, D.G. Gilliland, and D.G. Griffin Cancer Cell 7 2005 129
12. E. Weisberg, P. Manley, J. Mestan, S. Cowan-Jacob, A. Ray, and J.D. Griffin Br. J. Cancer 94 2006 1765
13. P.W. Manley, P. Drueckes, G. Fendrich, P. Furet, J. Liebetanz, G. Martiny-Baron, J. Mestan, J. Trappe, M. Wartmann, and D. Fabbro Biochim. Biophys. Acta 1804 2010 445
14. H.M. Kantarjian, F. Giles, N. Gattermann, K. Bhalla, G. Alimena, F. Palandri, G.J. Ossenkoppele, F.-E. Nicolini, S.G. O'Brien, M. Litzow, R. Bhatia, F. Cervantes, A. Haque, Y. Shou, D.J. Resta, A. Weitzman, A. Hochhaus, and P. le Coutre Blood 110 2007 3540
15. P. le Coutre, O.G. Ottmann, F. Giles, D.-W. Kim, J. Cortes, N. Gattermann, J.F. Apperley, R.A. Larson, E. Abruzzese, S.G. O'Brien, K. Kuliczkowski, A. Hochhaus, F.-X. Mahon, G. Saglio, M. Gobbi, Y.-L. Kwong, M. Baccarani, T. Hughes, G. Martinelli, J.P. Radich, M. Zheng, Y. Shou, and H. Kantarjian Blood 111 2008 1834
16. P.W. Manley, W. Breitenstein, J. Brüggen, S.W. Cowan-Jacob, P. Furet, J. Mestan, and T. Meyer Bioorg. Med. Chem. Lett. 14 2004 5793
17. B. Nagar, W.G. Bornmann, P. Pellicena, T. Schindler, D.R. Veach, W.T. Miller, B. Clarkson, and J. Kuriyan Cancer Res. 62 2002 4236
18. P.W. Manley, S.W. Cowan-Jacob, E. Buchdunger, D. Fabbro, G. Fendrich, P. Furet, T. Meyer, and J. Zimmermann Eur. J. Cancer 38 2002 S19
19. S.W. Cowan-Jacob, G. Fendrich, A. Floersheimer, P. Furet, J. Liebetanz, G. Rummel, P. Rheinberger, M. Centeleghe, D. Fabbro, and P.W. Manley Acta Crystallogr. D Biol. Crystallogr. 63 2007 80
20. S.W. Cowan-Jacob, V. Guez, G. Fendrich, J.D. Griffin, D. Fabbro, P. Furet, J. Liebetanz, J. Mestan, and P.W. Manley Mini-Rev. Med. Chem. 4 2004 285
21. J. Bajorath Chem. Inf. Comput. Sci. 41 2001 233
22. A. Schuffenhauer, P. Floersheim, P. Acklin, and E. Jacoby J. Chem. Inf. Comput. Sci. 43 2003 391
23. T. Cheeseright, M. Mackey, S. Rose, and A. Vinter J. Chem. Inf. Model. 46 2006 665
24. E. Day, B. Waters, K. Spiegel, T. Alnadaf, P.W. Manley, E. Buchdunger, C. Walker, and G. Jarai Eur. J. Pharmacol. 599 2008 44
25. C.B. Lozzio, and B.B. Lozzio Blood 45 1975 321
26. G.O. Daley, and D. Baltimore Proc. Natl. Acad. Sci. 85 1988 9312
27. M. Carroll, M.H. Tomasson, G.F. Barker, T.R. Golub, and D.G. Gilliland Proc. Natl. Acad. Sci. 93 1996 14845
28. Manley, P. W.; Mestan, J.; Meyer, T.; Fabbro, D. Proceedings of the 97th Annual Meeting of the American Association for Cancer Research, Apr 1-5, 2006; AACR: Washington, DC, Philadelphia (PA), 2006; p 7. Abstr. 30.
29. D.A. Tuveson, N.A. Willis, T. Jacks, J.D. Griffin, S. Singer, C.D. Fletcher, J.A. Fletcher, and G.D. Demetri Oncogene 20 2001 5054
30. I. Nakoinz, M.-T. Lee, J.F. Weaver, and P. Ralph J. Immunol. 145 1990 860
31. G.D. Demetri, P.G. Casali, J.-Y. Blay, M. von Mehren, J.A. Morgan, R. Bertulli, I. Ray-Coquard, P. Cassier, M. Davey, H. Borghaei, D. Pink, M. Debiec-Rychter, W. Cheung, S.M. Bailey, M.L. Veronese, A. Reichardt, E. Fumagalli, and P. Reichardt Clin. Cancer Res. 15 2009 5910
32. P. Willett, J.M. Barnard, and G.M. Downs J. Chem. Inf. Comput. Sci. 38 1998 983
33. P. Willett, and V. Winterman Quant. Struct.-Act. Relat. 5 1986 18
34. J.S. Delaney Mol. Divers. 1 1996 217
35. R.D. Brown, and Y.C. Martin SAR QSAR Environ. Res. 8 1998 23
36. D.R. Flower J. Chem. Inf. Comput. Sci. 38 1998 379
37. L. Xue, J. Godden, and J. Bajorath J. Chem. Inf. Comput. Sci. 39 1999 881
38. Y.C. Martin, J.L. Kofron, and L.M. Traphagen J. Med. Chem. 45 2002 4350
39. Z. Szakács, S. Béni, Z. Varga, L. Örfi, G. Kéri, and B. Noszál J. Med. Chem. 48 2005 249
40. J. Thomas, L. Wang, R.E. Clark, and M. Pirmohamed Blood 104 2004 3739
41. D.L. White, V.A. Saunders, P. Dang, J. Engler, A.C. Zannettino, A.C. Cambareri, S.R. Quinn, P.W. Manley, and T.P. Hughes Blood 108 2006 697
42. A. Haouala, H. Rumpold, G. Untergasser, T. Buclin, H.-B. Ris, N. Widmer, and L.A. Decosterd Drug Met. Lett. 4 2010 114
43. L. Wang, A. Giannoudis, S. Lane, P. Williamson, M. Pirmohamed, and R.E. Clark Clin. Pharmacol. Ther. 83 2008 258
44. D.L. White, P. Dang, J. Engler, A. Venables, S. Zrim, M. Osborn, V.A. Saunders, P.W. Manley, and T.P. Hughes J. Clin. Oncol. 28 2010 2761
45. A. Davies, N.E. Jordanides, A. Giannoudis, C.M. Lucas, S. Hatziieremia, R.J. Harris, R.E. Jørgensen, T.L. Holyoake, M. Pirmohamed, R.E. Clark, and J.C. Mountford Leukemia 23 2009 1999
46. N. Vajpai, A. Strauss, G. Fendrich, S.W. Cowan-Jacob, P.W. Manley, S. Grzesiek, and W. Jahnke J. Biol. Chem. 283 2008 18292
47. C.D. Blanke, C. Rankin, G.D. Demetri, C.W. Ryan, M. von Mehren, R.S. Benjamin, A.K. Raymond, V.H.C. Bramwell, L.H. Baker, R.G. Maki, M. Tanaka, J.R. Hecht, M.C. Heinrich, C.D.M. Fletcher, J.J. Crowley, and E.C. Borden J. Clin. Oncol. 26 2008 626
48. J.F. Apperley, M. Gardembas, J.V. Melo, R. Russell-Jones, B.J. Bain, E.J. Baxter, A. Chase, J.M. Chessells, M. Colombat, C.E. Dearden, S. Dimitrijevic, F.-X. Mahon, D. Marin, Z. Nikolova, E. Olavarria, S. Silberman, B. Schultheis, N.C.P. Cross, and J.M.N. Goldman Engl. J. Med. 347 2002 481
49. J.-Y. Blaye, H. El Sayadi, P. Thiesse, J. Garret, and I. Ray-Coquard Ann. Oncol. 19 2008 821
50. R.A. Larson, B.J. Druker, F. Guilhot, G.G. O'Brien, G.J. Riviere, T. Krahnke, I. Gathmann, and Y. Wang Blood 111 2008 4022
51. U. Rix, O. Hantschel, G. Dürnberger, L.L. Remsing Rix, M. Planyavsky, N.V. Fernbach, I. Kaupe, K.L. Bennett, P. Valent, J. Colinge, T. Köcher, and G. Superti-Furga Blood 110 2007 4055
52. D. Marin, A. Bazeos, F.-X. Mahon, L. Eliasson, D. Milojkovic, M. Bua, J.F. Apperley, R. Szydlo, R. Desai, K. Kozlowski, C. Paliompeis, V. Latham, L. Foroni, M. Molimard, A. Reid, K. Rezvani, H. de Lavallade, C. Guallar, J. Goldman, and J.S. Khorashad J. Clin. Oncol. 28 2010 2381
53. J.E. Cortes, D. Jones, S. O'Brien, E. Jabbour, M. Konopleva, A. Ferrajoli, T. Tapan Kadia, G. Borthakur, D. Stigliano, J. Shan, and H. Kantarjian J. Clin. Oncol. 28 2010 392
54. C. Tanaka, O. Yin, V. Sethuraman, T. Smith, X.F. Wang, K. Grouss, H. Kantarjian, F. Giles, O.G. Ottmann, L. Galitz, and H. Schran Clin. Pharmacol. Ther. 87 2010 197
55. G. Saglio, D.-W. Kim, S. Issaragrisil, P. Le Coutre, G. Etienne, C. Lobo, R. Pasquini, R.E. Clark, A. Hochhaus, T.P. Hughes, N. Gallagher, A. Hoenekopp, M. Dong, A. Haque, R.A. Larson, and H.M. Kantarjian New Engl. J. Med. 362 2010 2251
56. S. Parkkila, A. Innocenti, H. Kallio, M. Hilvo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 19 2009 4102
57. C. Shimazaki, N. Ochiai, R. Uchida, S.-I. Fuchida, A. Okano, E. Ashihara, T. Inaba, N. Fujita, and M. Nakagawa Leukemia 17 2003 804
58. S. Sadis, A. Mukherjee, S. Olson, M. Dokmanovich, R. Maher, C.-H. Cai, L. Vu, M. Crawford, R. Fedechko, L. Whitfield, T. Stock, M-P. Hellio Le Graverand-Gastineau, and B. Zeiher Arthritis Rheum. 60 2009 408 10.1002/art.25491
59. H.-J. Roth Curr. Opin. Chem. Biol. 9 2005 293
60. S. Tanimoto, and T.A. Pavlidis Comput. Graph Image Process. 4 1975 104
61. K. Okuda, T.R. Golub, D.G. Gilliland, and J.D. Griffin Oncogene 13 1996 1147
62. M. Sattler, R. Salgia, K. Okuda, N. Uemura, M.A. Durstin, E. Pisick, G. Xu, J.L. Li, K.V. Prasad, and J.D. Griffin Oncogene 12 1996 839
63. T.R. Golub, G.F. Barker, M. Lovett, and G.D. Gilliland Cell 77 1994 307
64. B. Faller, H.P. Grimm, F. Loeuillet-Ritzler, S. Arnold, and X. Briand J. Med. Chem. 48 2005 2571
65. P. Ertl, B. Rohde, and P. Selzer J. Med. Chem. 43 2000 3714