Oseltamivir phosphate. Anti-influenza neuraminidase (sialidase) inhibitor

Drugs of the Future

Volumn 24, Issue 11, 1999, Pages 1189-1202

  Graul, A ^a   Leeson, P A ^a   Castaner J ^a  

^a PROUS SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETAMIDO 3 GUANIDINOBENZOIC ACID; 4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; AMANTADINE; ARBIDOL; OSELTAMIVIR; PERAMIVIR; RIMANTADINE; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ZANAMIVIR;

ANTIVIRAL ACTIVITY; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CYTOTOXICITY; DOUBLE BLIND PROCEDURE; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; ENZYME INHIBITION; HUMAN; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS B; MULTICENTER STUDY; NAUSEA; NONHUMAN; RANDOMIZED CONTROLLED TRIAL; REVIEW; VOMITING;

EID: 0033373210     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1999.024.11.555874     Document Type: Review

References (68)

1. Kent, K.M., Kim, C.U., McGee, L.R., Munger, J.D., Prisbe, E.J., Postich, M.J., Rohloff, J.C., Kelly, D.E., Williams, M.A., Zhang, L. (Gilead Sciences, Inc.). Preparation of carbocyclic cpds. US 5886213.
2. Kent, K.M., Kim, C.U., McGee, L.R., Munger, J.D., Prisbe, E.J., Postich, M.J., Rohloff, J.C., St. John, D.E., Williams, M.A., Zhang, L. (Gilead Sciences, Inc.). Preparation of cyclohexene carboxylate derivatives. WO 9807685.
3. Bisohofberger, N.W., Dahl, T.C., Hitchcock, M.J.M., Kim, C.U., Lew, W., Liu, H., Mills, R.G., Williams, M.A. (Gilead Sciences, Inc.). Cpds. containing six-membered rings, processes for their preparation, and their use as medicaments. WO 9914185.
4. Rohloff, J.C., Kent, K.M., Postich, M.J. et al. Practical total synthesis of the anti-influenza drug GS-4104. J Org Chem 1998, 63: 4545-50.
5. Bischofberger, N.W., Kim, C.U., Lew, M., Liu, H., Williams, M.A. (Gilead Sciences, Inc.). Carbocyclic cpds. US 5763483.
6. Bischofberger, N.W., Kim, C.U., Lew, W., Liu, H., Williams, M.A. (Gilead Sciences, Inc.). Cpds. and methods for synthesis and therapy. EP 759917, JP 99501908, US 5952375, WO 9626933.
7. Lui, K.J., Kendal, A.P. Impact of influenza epidemics on mortality in the United States from October 1972 to May 1985. Am J Public Health 1987, 77: 712-6.
8. CDC. Prevention and control of influenza recommendations of the Advisory Committee on Immunization Practices (ACIP). MMWR 1999, 48 (no. RR-4).
9. Colacino, J.M., Staschke, K.A., Laver, W.G. Approaches and strategies for the treatment of influenza virus infections. Antivir Chem Chemother 1999, 10: 155-85.
10. Webster, R.G., Kawaoka, Y. Influenza: An emerging and reemerging disease. Semin Virol 1994, 5: 103-11.
11. Cox, N.J., Fukuda, K. Influenza. Infect Dis Clin North Am 1998, 12: 27-38.
12. Pinto, L.H., Holsinger, L.J., Lamb, R.A. Influenza virus M2 protein has ion channel activity. Cell 1992, 69: 517-28.
13. Hayden, F.G., Couch, R.B. Clinical and epidemiological importance of influenza A viruses resistant to amantadine and rimantadine. Rev Med Virol 1992, 2: 89-96.
14. Glushkov, R.G. Arbidol. Drugs Fut 1992, 17: 1079-81.
15. Palese, P., Compans, R.W. Inhibition of influenza virus replication in tissue culture by 2-deoxy-2,3-dehydro-N-trifluoroacetyl-neuraminic acid (FANA): Mechanism of action. J Gen Virol 1976, 33: 159-63.
16. Klenk, H.D., Rott, R. The molecular biology of influenza virus pathogenicity. Adv Virus Res 1988, 34: 247-81.
17. Liu, C., Eichelberger, M.C., Compans, R.W., Air, G.M. Influenza type A virus neuraminidase does not play a role in viral entry, replication, assembly, or budding. J Virol 1995, 69: 1099-106.
18. Colman, P.M., Varghese, J.N., Laver, W.G. Structure of the catalytic and antigenic sites in influenza virus neuraminidase. Nature 1983, 303: 41-4.
19. Colman, P.M. Influenza virus neuraminidase: Structure, antibodies, and inhibitors. Protein Sci 1994, 3: 1687-96.
20. Varghese, J.N., McKimm-Breschkin, J.L., Caldwell, J.B., Kortt, A.A., Colman, P.M. The structure of the complex between influenza virus neuraminidase and sialic acid, the viral receptor. Proteins 1992, 14: 327-32.
21. Von Itzstein, M., Wu, W.Y., Kok, G.B. et al. Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature 1993, 363: 418-23.
22. Relenza receives approval in the E.U. for treatment of influenza. DailyDrugNews.com (Daily Essentials) June 3, 1999.
23. Kim, C.U. Rational drug design of orally active influenza neuraminidase inhibitors: Discovery and development of GS 4104. Med Chem Res 1998, 8: 392-9.
24. Kim, C.U., Lew, W., Williams, M.A., Wu, H., Zhang, L., Chen, X., Escarpe, P.A., Mendel, D.B., Laver, W.G., Stevens, R.C. Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors. J Med Chem 1998, 41: 2451-60.
25. Kim, C.U., Lew, W., Williams, M.A. et al. Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent antiinfluenza activity. J Am Chem Soc 1997, 119: 681-90.
26. Williams, M.A., Lew, W., Mendel, D.B., Tai, C.Y., Escarpe, P.A., Laver, W.G., Stevens, R.C., Kim, C.U. Structure-activity relationships of carbocyclic influenza neuraminidase inhibitors. Bioorg Med Chem Lett 1997, 7: 1837-42.
27. Hayden, F.G., Rollins, B.S. In vitro activity of the neuraminidase inhibitor GS4071 against influenza viruses. Antivir Res 1997, 34(2): Abst 159.
28. Huffman, J.H., Morrison, A., Syndergaard, T., Sidwell, R.W. Synergistic in vitro anti-influenza virus effects of the neuraminidase inhibitor GS4071 and ribavirin. Antivir Res 1998, 37(3): Abst 172.
29. Mendel, D.B., Escarpe, P.A., Tai, C.Y., Williams, M.A., Lew, W., Wu, H., Kim, C.U., Laver, G., Graves, B.J. Kinetic studies of the inhibition of influenza neuraminidases by GS4071. Antivir Res 1998, 37(3): Abst 171.
30. Mendel, D.B., Tai, C.Y., Escarpe, P.A. In vitro selection and characterization of a human influenza virus with decreased susceptibility to GS4071. Antivir Res 1998, 37(3): Abst 113.
31. Tai, C.Y., Escarpe, P.A., Sidwell, R.W., Williams, M.A., Lew, W., Wu, H., Kim, C.U., Mendel, D.B. Characterization of human influenza virus variants selected in vitro in the presence of the neuraminidase inhibitor GS4071. Antimicrob Agents Chemother 1998, 42: 3234-41.
32. Li, W., Escarpe, P.A., Eisenberg, E.J. et al. Identification of GS4104 as an orally bioavailable prodrug of the influenza virus neuraminidase inhibitor GS4071. Antimicrob Agents Chemother 1998, 42: 647-53.
33. Sidwell, R.W., Huffman, J.H., Barnard, D.L., Bailey, K.W., Wong, M.H., Morrison, A., Syndergaard, T., Kim, C.U. Inhibition of influenza virus infections in mice by GS4104, an orally effective influenza virus neuraminidase inhibitor. Antivir Res 1998, 37: 107-20.
34. Mendel, D.B., Tai, C.Y., Escarpe, P.A. et al. Oral administration of a prodrug of the influenza virus neuraminidase inhibitor GS4071 protects mice and ferrets against influenza infection. Antimicrob Agents Chemother 1998, 42: 640-6.
35. Sidwell, R.W., Bailey, K.W., Bemis, P.A., Wong, M.H., Eisenberg, E.J., Huffman, J.H. Influence of treatment schedule and viral challenge dose on the in vivo influenza virus-inhibitory effects of the orally administered neuraminidase inhibitor GS4104. Antivir Chem Chemother 1999, 10: 187-93.
36. Sidwell, R.W., Bailey, K.W., Wong, M.H., Huffman, J.H. Lack of in vivo development of influenza A virus resistance to the orally effective neuraminidase inhibitor GS4104. Antivir Res 1998, 37(3): Abst 112.
37. Eisenberg, E.J., Bidgood, A., Cundy, K.C. Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104. Antimicrob Agents Chemother 1997, 41: 1949-52.
38. Cundy, K.C., Eisenberg, G., Bidgood, A., Li, W., Mendel, D., Francis, R.J., Angus, D., Sharp, S.R., Lee, W.A. The novel influenza neuraminidase inhibitor prodrug GS4104 is highly bioavailable in animals. 37th Intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst H-135.
39. Cundy, K.C., Eisenberg, G., Bidgood, A., Lynch, G., Lee, W.A. Enhanced delivery of the novel influenza neuraminidase inhibitor GS4071 to rat lung after oral administration of the prodrug GS4104. 37th Intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst A-122.
40. Wood, N.D., Aitken, M., Sharp, S., Evison, H. Tolerability and pharmacokinetics of the influenza neuraminidase inhibitor Ro 64-0802 (GS4071) following oral administration of the prodrug Ro 64-0796 (GS4104) to healthy male volunteers. 37th Intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst A-123.
41. Algranati, N.E., Massarella, J.W., Wood, N.D., Rana, B., Aitken, M., Freestone, S., Brown, A., Ward, P. Pharmacokinetics and tolerability of the influenza neuraminidase inhibitor Ro 64-0802 following multiple dose oral administration of the prodrug Ro 64-0796 to healthy young and elderly subjects. Eur Repir J 1998, 12(Suppl. 28): Abst P1066.
42. He, G., Massarella, J., Schulz, R., Calvert, L., Woodruffe-Peacock, C., Dorr, A., Ward, P., Krimmer, D., Brown, A. The relative bioavailability of early clinical and market formulations of the novel oral neuraminidase inhibitor Ro 64-0796/GS4104. Fundam Clin Pharmacol 1999, 13(Suppl. 1): Abst PW177.
43. He, G., Massarella, J., Aitken, M., Dorr, A., Calvert, L., Butcher, R., Brown, A., Ward, P. The pharmacokinetics and safety of the oral neuraminidase inhibitor Ro 64-0796/GS4104 when administered concurrently with cimetidine or probenecid in healthy subjects. J Antimicrob Chemother 1999, 44(Suppl. A): Abst P17.
44. Hayden, F.G., Fritz, R.S., Lobo, M., Kinnersley, N., Mills, R.G., Straus, S.E. Effects of the oral neuraminidase inhibitor GS4104 on cytokine responses during experimental human influenza A virus infection. Eur Respir J 1998, 12(Suppl. 28): Abst 1791.
45. Hayden, F.G., Lobo, M., Treanor, J.J., Miller, M., Mills, R.G. Efficacy and tolerability of oral GS4104 for early treatment of experimental influenza in humans. 37th intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst LB-26.
46. Hayden, F.G., Treanor, J.J., Fritz, R.S., Lobo, M., Betts, R.F., Miller, M., Kinnersley, N., Mills, R.G., Ward, P., Straus, S.E. Use of the oral neuraminidase inhibitor oseltamivir in experimental human influenza: Randomized controlled trials for prevention and treatment. JAMA - J Am Med Assoc 1999, 282: 1240-6.
47. Treanor, J.J., Vrooman, P.S., Hayden, F.G., Kinnersley, N., Ward, P., Mills, R.G. Efficacy of oral GS4104 in treating acute influenza. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24-27, San Diego) 1998, Abst LB-4.
48. Aoki, F., Osterhaus, A., Rimmelzwaan, G., Kinnersley, N., Ward, P. Oral GS4104 successfully reduces duration and severity of naturally acquired influenza. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24-27, San Diego) 1998, Abst LB-5.
49. Oxford, J., Ward, P., Kinnersley, N. Influenza treatment with GS4104 reduces viral load and antibiotic use related to respiratory complications. Eur Respir J 1999, 14(Suppl. 30): Abst P1722.
50. Nicholson, K.G., Ward, P., Kinnersley, N. Oral GS4104 in the treatment of influenza in adults is effective and reduces influenza-related complications and need for antibiotic treatment. J Antimicrob Chemother 1999, 44(Suppl. A): Abst P5.
51. Hayden, F.G., Atmar, R.L., Schilling, M. et al. Use of the selective oral neuraminidase inhibitor oseltamivir to prevent influenza. New Engl J Med 1999, 341: 1336-43.
52. Jefferson, T., Wegmüller, Y., Barker, C., Ward, P. The impact of influenza on the workplace and the effect of the antiviral GS4104 on daily performance and work absenteeism. J Antimicrob Chemother 1999, 44(Suppl. A): Abst P23.
53. Treatment with Tamiflu reduces secondary complications of influenza and need for antibiotics. DailyDrugNews.com (Daily Essentials) Oct 14, 1999.
54. Tamiflu, first oral influenza neuraminidase inhibitor, launched today in Switzerland. DailyDrugNews.com (Daily Essentials) Oct 1, 1999.
55. Roche's breakthrough flu treatment approved in Switzerland. DailyDrugNews.com (Daily Essentials) Sept 27, 1999.
56. Tamiflu approved in time for U.S. flu season. DailyDrugNews.com (Daily Essentials) Oct 28, 1999.
57. Tamiflu™ (oseltamivir phosphate) capsules. Roche Laboratories Inc. Product Fact Sheet, Oct 1999.
58. Huffman, J.H., Morrison, A., Stowell, V., Barnard, D.L., Bush, K., Sidwell, R.W. Potent in vitro infuenza virus-inhibitory activity of a series of cyclopentane neuraminidase inhibitors. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26-29, San Francisco) 1999, Abst F946.
59. Sollis, S.L.et al. Novel inhibitors of influenza sialidase related to GG167- Synthesis of 4-amino and guanidino-4H-pyran-2-carboxylic acid-6-propylamides, selective inhibitors of influenza A virus sialidase. Bioorg Med Chem Lett 1996, 6: 1805.
60. Kim, C.U., Lew, W., Williams, M.A., Wu, H., Zhang, L., Chen, X., Escarpe, P.A., Mendel, D.B., Laver, W.G., Stevens, R.C. Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors. J Med Chem 1998, 41: 2451-60.
61. Zhang, L. et al. Synthesis and activity of C2-substituted analogs of influenza neuraminidase inhibitor GS4071. Bioorg Med Chem Lett 1997, 7: 1847.
62. Smith, P.W., Robinson, J.E., Evans, D.N., Sollis, S.L., Howes, P.D., Trivedi, N., Bethell, R.C. Sialidase inhibitors related to zanamivir: Synthesis and biological evaluation of 4H-pyran 6-ether and ketone. Bioorg Med Chem Lett 1999, 9: 601-4.
63. Bantia, S., Ananth, S., Andries, K., Horn, L., Parker, C., Chand, P., Babu, Y. In vitro activity of the neuraminidase inhibitor RWJ-270201 (BCX-1812) against influenza virus. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26-29, San Francisco) 1999, Abst F947.
64. Chandler, M., Bamford, M.J., Conroy, R. et al. Synthesis of the potent influenza neuraminidase inhibitor 4-guanidino Neu5Ac2en. X-Ray molecular structure of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-erythro-L-gluconononic acid. J Chem Soc - Perkins Trans I 1995, 9: 1173.
65. Bethell, R. Sialidase as a target for inhibitors of influenza virus replication. IBC Conf Antivir. Latest Preclin Clin Dev Infect Dis (June 26-27, Washington DC) 1997.
66. Smith, P.W. et al. Novel inhibitors of influenza sialidases related to GG167. Structure-activity, crystallographic and molec ular dynamics studies with 4H-pyran-2-carboxylic acid 6-carboxamides. Bioorg Med Chem Lett 1996, 6: 2931.
67. Starkey, I.D., Mahmoudian, M., Noble, D., Smith, P.W., Cherry, P.C., Howes, P.D., Sollis, S.L. Synthesis and influenza virus sialidase inhibitory activity of the 5-desacetamido analogue of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid (GG167). Tetrahedron Lett 1995, 36: 299.
68. Woods, J.M., Bethell, R.C., Coates, J.A. et al. 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro. Antimicrob Agents Chemother 1993, 37: 1473-9.