Zanamivir antiviral: Influenza neuraminidase inhibitor

Drugs of the Future

Volumn 21, Issue 4, 1996, Pages 375-382

  Fromtling, Robert A ^a   Castaner J ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b PROUS SCIENCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2' FLUORO 2' DEOXYGUANOSINE; AMANTADINE; ANTIVIRUS AGENT; GUANOSINE DERIVATIVE; RIBAVIRIN; RIMANTADINE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS SIALIDASE; ZANAMIVIR;

ANTIVIRAL ACTIVITY; ARTICLE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CYTOTOXICITY; DOUBLE BLIND PROCEDURE; DRUG BIOAVAILABILITY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS B; INHALATIONAL DRUG ADMINISTRATION; INTRANASAL DRUG ADMINISTRATION; INTRAPERITONEAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; MOLECULAR WEIGHT; NONHUMAN; ORAL DRUG ADMINISTRATION; PHASE 1 CLINICAL TRIAL; PHASE 2 CLINICAL TRIAL; RANDOMIZED CONTROLLED TRIAL; VIRUS INHIBITION;

EID: 0030013606     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1996.021.04.350760     Document Type: Article

References (38)

1. 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-gluco-nononic acid. J Chem Soc PerkinTrans 1 1995, 1173-80.
2. Von Itzstein, M., Wu, W.-Y., Jin, B. The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: A potent influenza virus sialidase inhibitor. Carbohydr Res 1994, 259: 301-5.
3. Chandler, M., Weir, N.G. (Glaxo Group Ltd.). Preparation of N-acetyl neuraminic derivs. WO 9312105.
4. Weir, N.G., Chandler, M., Bamford, M.J. (Glaxo Group Ltd.). Synthesis of N-acetyl neuraminic acid derivs. WO 9407885.
5. Patel, V. (Glaxo Group Ltd.). Synthesis of N-acetyl neuraminic acid derivs. WO 9407886.
6. Von Itzstein, L.M., Wu, W.-Y., Phan, T., Danylec, B. (Biota Scientific Management PTY Ltd.). Derivs. and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid and their use as antiviral agents. WO 9116320.
7. Penn, C.R., Ryan, D.M., Woods, J.M., Bethell, R.C., Hotham, V.J., Colman, P., Wu, W.-Y., Von Itzstein, M. Novel selective inhibitors of influenza virus neuraminidase inhibit replication of virus in cell culture and in animal models. 32nd Intersci Conf Antimicrob Agents Chemother (Oct 11-14, Anaheim) 1992, Abst 1325.
8. 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.
9. Woods, J.M. Design and development of neuraminidase inhibitors for influenza virus. 7th Eur Cong Clin Microbiol Infect Dis (March 26-30, Vienna) 1995, Abst 54.
10. Merck Manual of Diagnosis and Therapy, 16th Edition, R. Berkow (Ed.), Merck Research Laboratories, Rahway, 1992, 271-2.
11. Ziegler, T., Cox, N.J. Influenza viruses. In: Manual of Clinical Microbiology, 6th Edition, P.R. Murray, E.J. Barron, M.A. Pfaller, F.C. Tenover and R.H. Yolken (Eds.), ASM Press, Washington DC, 1995, 918-25.
12. Kilbourne, E.D. Influenza. Plenum Publishing Corp., New York, 1987.
13. Murphy, B.R., Webster, R.G. Orthomyxoviruses. In: Virology, 2nd Edition, B.N. Fields, D.M. Knipe (Eds.), Raven Press, New York, 1990, 1091-152.
14. Wilson, I.A., Skehel, J.J., Wiley, D.C. Structure of the haemagglutinin membrane glycoprotein on influenza virus at 3 Å resolution. Nature 1981, 289: 366-73.
15. Wiley, D.C., Wilson, I.A., Skehel, J.J. Structural identification of the antibody-binding sites of Hong Kong influenza haemagglutinin and their involvement in antigenic variation. Nature 1981, 289: 373-8.
16. Varghese, J.N., Laver, W.G., Colman, P.M. Structure of the influenza virus glycoprotein antigen neuraminadase at 2.9 Å resolution. Nature 1983, 303: 35-40.
17. Colman, P.M., Varghese, J.N., Laver, W.G. Structure of the catalytic and antigenic sites in influenza virus neuraminadase. Nature 1983, 303: 41-4.
18. Chong, A.K.J., Pegg, M.S., Von Itzstein, M. Characterisation of an ionisable group involved in binding and catalysis by sialidase from influenza virus. Biochem Int 1991, 24: 165-71.
19. Chong, A.K.J., Pegg, M.S., Taylor, N.R., Von Itzstein, M. Evidence for a sialosyl cation transition-state complex in the reaction of sialidase from influenza virus. Eur J Biochem 1992, 207: 335-43.
20. Pegg, M.S., Von Itzstein, M. Slow-binding inhibition of sialidase from influenza virus. Biochem Mol Biol Int 1994, 32: 851-8.
21. Taylor, N.R., Von Itzstein, M. Molecular modeling studies on ligand binding to sialidase from influenzae virus and the mechanism of catalysis. J Med Chem 1994, 37: 616-24.
22. 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-deacetamido analogue of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid (GG167). Tetrahedron Lett 1995, 36: 299-302.
23. Penn, C.R., Hiscox, S.A., Fenton, R., Ryan, D.M., Woods, J.M. 4-Guanidino-Neu5Ac2en is a potent and selective inhibitor of influenza virus replication in vitro and in vivo. 9th Int Cong Virol (Aug 8-13, Glasgow) 1993, Abst W26-5.
24. Woods, J.M., Hiscox, S.A., Ryan, D.M., Penn, C.R. 4-Guanidino-Neu5Ac2en is a potent and broad spectrum inhibitor of influenza A and B viruses, in vitro and in vivo. Antivir Res 1993, 20(Suppl. 1): Abst 101.
25. Woods, J.M., Bethell, R.C., Coates, J.A.V. 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.
26. Thomas, G.P., Forsyth, M., Penn, C.R., McCauley, J.W. Inhibition of the growth of influenza viruses in vitro by 4-guanidino-2,4-dideoxy-N-acetylneuraminic acid. Antivir Res 1994, 24: 351-6.
27. Hayden, F.G., Rollins, B.S., Madren, L.K. Anti-influenza virus activity of the neuraminidase inhibitor 4-guanidino-Neu5Ac2en in cell culture and in human respiratory epithelium. Antivir Res 1994, 25: 123-34.
28. Madren, L.K., Shipman, C. Jr., Hayden, F.G. In vitro inhibitory effects of combinations of anti-influenza agents. Antivir Chem Chemother 1995, 5: 109-13.
29. Hayden, F.G., Cote, K.M., Douglas, R.G. Jr. Plaque inhibition assay for drug susceptibility testing of influenza viruses. Antimicrob Agents Chemother 1980, 17: 865-70.
30. Hayden, F.G., Belshe, R.B., Clover, R.D., Hay, A.J., Oakes, M.G., Soo, W. Emergence and apparent transmission of rimanta-dine-resistant influenza A virus in families. New Engl J Med 1989, 321: 1696-702.
31. Schulman, J. The use of an animal model to study transmission of influenza virus infection. Amer J Public Health 1968, 58: 2092-6.
32. Smith, H., Sweet, C. Lessons for human influenza from pathogenicity studies with ferrets. Rev Infect Dis 1988, 10: 56-75.
33. Fenton, R.J., Ashton, C.J., Dempsey, M.H., Lambourne, J., Ryan, D.M., Ticehurst, J., Penn, C.R. Anti-influenza virus activities of two novel neuraminidase (sialidase) inhibitors in both mouse and ferret animal models. 18th Int Cong Chemother (June 27-July 2, Stockholm) 1993, Abst 1650.
34. Ryan, D.M.,Ticehurst, J., Dempsey, M.H., Penn, C.R. Inhibition of influenza virus replication in mice by GG167 (4-guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid) is consistent with extracellular activity of viral neuraminidase (sialidase). Antimicrob Agents Chemother 1994, 38: 2270-5.
35. Efthymiopoulos, C., Barrington, P., Patel, J., Harker, A., Harris, A., Hussey, E.K., Bye, A. Pharmacokinetics of the neuraminidase inhibitor 4-guanidino Neu5Ac2en (GG167) following intravenous, intranasal and inhaled administration in man. 34th Intersci Conf Antimicrob Agents Chemother (Oct 4-7, Orlando) 1994, Abst H70.
36. Hussey, E., Hayden, F., Grosse, C., Eason, C., Morris, D. Serum and urine GG167 concentrations in healthy subjects inoculated experimentally with influenza A virus. 35th Intersci Conf Antimicrob Agents Chemother (Sept 17-20, San Francisco) 1995, Abst A132.
37. Hayden, F., Lobo, M., Esinhart, J., Hussey, E. Efficacy of 4-guanidino Neu5Ac2en in experimental human influenza A virus infection. 34th Intersci Conf Antimicrob Agents Chemother (Oct 4-7, Orlando) 1994, Abst H35.
38. Hayden, F.G., Treanor, J.J., Esinhart, J., Eason, C.U., Hussey, E.K. Twice daily intranasal GG167 for experimental influenza A. Antivir Res 1995, 26: Abst 140.