Laninamivir and its prodrug, CS-8958: Long-acting neuraminidase inhibitors for the treatment of influenza

Antiviral Chemistry and Chemotherapy

Volumn 21, Issue 2, 2010, Pages 71-84

  Yamashita, Makoto ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INAVIR; LANINAMIVIR; LANINAMIVIR OCTANOATE; OSELTAMIVIR; SIALIDASE; UNCLASSIFIED DRUG; ZANAMIVIR;

DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; IN VIVO STUDY; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H5N1; INFLUENZA VIRUS B; NONHUMAN; PANDEMIC INFLUENZA; PHASE 1 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; REVIEW; SINGLE DRUG DOSE;

ANIMALS; ANTIVIRAL AGENTS; DISEASE MODELS, ANIMAL; DRUG ADMINISTRATION ROUTES; DRUG ADMINISTRATION SCHEDULE; HUMANS; INFLUENZA, HUMAN; MICE; NEURAMINIDASE; ORTHOMYXOVIRIDAE; OSELTAMIVIR; PANDEMICS; PRODRUGS; RATS; ZANAMIVIR;

EID: 78751692669     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.3851/IMP1688     Document Type: Review

References (47)

1. Wright PF, Webster RG. Orthomyxoviruses. In Knipe DM, Howley PM, Griffin DE, et al. (Editors). Fields virology. 4th Ed. Philadelphia: Lippincott Williams & Wilkins 2001; pp. 1534-1579.
2. Fiore AE, Shay DK, Haber P, et al. Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP), 2007. MMWR Recomm Rep 2007; 56:1-54.
3. Novel Swine-Origin Influenza A (H1N1) Virus Investigation Team. Emergence of a novel swine-origin influenza A (H1N1) virus in humans. N Engl J Med 2009; 360:2605-2615.
4. Itoh Y, Shinya K, Kiso M, et al. In vitro and in vivo characterization of new swine-origin H1N1 influenza viruses. Nature 2009; 460:1021-1025.
5. Munster VJ, de Wit E, van den Brand JM, et al. Pathogenesis and transmission of swine-origin 2009 A (H1N1) influenza virus in ferrets. Science 2009; 325:481-483.
6. Maines TR, Jayaraman A, Belser JA, et al. Transmission and pathogenesis of swine-origin 2009 A (H1N1) influenza viruses in ferrets and mice. Science 2009; 325:484-487.
7. Jain S, Kamimoto L, Bramley AM, et al. Hospitalized patients with 2009 H1N1 influenza in the United States, April-June 2009. N Engl J Med 2009; 361:1935-1944.
8. World Health Organization. Pandemic (H1N1) 2009 - update 107. (Updated 7 July 2010. Accessed 27 October 2010.) Available from http://www.who.int/csr/don/ 2010-07-02/en/index.html
9. Centres for Disease Control and Prevention. Updated CDC estimates of 2009 H1N1 influenza cases, hospitalizations and deaths in the United States, April 2009 - April 10, 2010. (Updated 10 April 2010. Accessed 27 October 2010.) Available from http://www.cdc.gov/h1n1flu/estimates-2009-h1n1.htm
10. Yuen KY, Chan PKS, Peiris M, et al. Clinical features and rapid viral diagnosis of human disease associated with avian influenza A H5N1 virus. Lancet 1998; 351:467-471. (Pubitemid 28070092)
11. Subbarao K, Klimov A, Katz J, et al. Characterization of an avian influenza A (H5N1) virus isolated from a child with a fatal respiratory illness. Science 1998; 279:393-396.
12. Claas EC, Osterhaus AD, van Beek R, et al. Human influenza A H5N1 virus related to a highly pathogenic avian influenza virus. Lancet 1998; 351:472-477.
13. World Health Organization. Confirmed human cases of avian influenza A(H5N1). (Accessed 27 October 2010.) Available from http://www.who.int/csr/ disease/avian-influenza/country/en/
14. Davies WL, Grunert RR, Haff RF, et al. Antiviral activity of 1-adamantanamine (amantadine). Science 1964; 144:862-863.
15. Bright RA, Shay DK, Shu B, et al. Adamantane resistance among influenza A viruses isolated early during the 2005-2006 influenza season in the United States. JAMA 2006; 295:891-894.
16. Bright RA, Medina MJ, Xu X, et al. Incidence of adamantane resistance among influenza A (H3N2) viruses isolated worldwide from 1994 to 2005: a cause for concern. Lancet 2005; 366:1175-1181.
17. Centers for Disease Control and Prevention. High levels of adamantane resistance among influenza A (H3N2) viruses and interim guidelines for use of antiviral agents - United States, 2005-06 influenza season. MMWR Morb Mortal Wkly Rep 2006; 55:44-46.
18. Cheung CL, Rayner JM, Smith GJ, et al. Distribution of amantadine-resistant H5N1 avian influenza variants in Asia. J Infect Dis 2006; 193:1626-1629.
19. Schunemann HJ, Hill SR, Kakad M, et al. WHO Rapid Advice Guidelines for pharmacological management of sporadic human infection with avian influenza A (H5N1) virus. Lancet Infect Dis 2007; 7:21-31.
20. Gubareva LV. Molecular mechanisms of influenza virus resistance to neuraminidase inhibitors. Virus Res 2004; 103:199-203.
21. Hatakeyama S, Sugaya N, Ito M, et al. Emergence of influenza B viruses with reduced sensitivity to neuraminidase inhibitors. JAMA 2007; 297:1435-1442.
22. Hayden FG. Antiviral resistance in influenza viruses - implications for management and pandemic response. N Engl J Med 2006; 354:785-788.
23. Kiso M, Mitamura K, Sakai-Tagawa Y, et al. Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet 2004; 364:759-765. (Pubitemid 39165094)
24. Lackenby A, Hungnes O, Dudman SG, et al. Emergence of resistance to oseltamivir among influenza A(H1N1) viruses in Europe. Euro Surveill 2008; 13:8026.
25. Le QM, Kiso M, Someya K, et al. Avian flu: isolation of drug-resistant H5N1 virus. Nature 2005; 437:1108.
26. World Health Organization. Influenza A(H1N1) virus resistance to oseltamivir - 2008/2009 influenza season, northern hemisphere. (Updated 18 March 2009. Accessed 27 October 2010.) Available from http://www.who.int/csr/disease/ influenza/H1N1webupdate20090318%20ed-ns.pdf
27. Centres for Disease Control and Prevention. 2008-2009 Influenza season week 15 ending April 18, 2009. (Updated 18 April 2009. Accessed 27 October 2010.) Available from http://www.cdc.gov/flu/weekly/weeklyarchives2008-2009/ weekly15.htm
28. World Health Organization. Weekly update on oseltamivir resistance to pandemic influenza A (H1N1) 2009 viruses. (Updated 14 April 2010. Accessed 27 October 2010.) Available from http://www.who.int/csr/disease/swineflu/ oseltamivirresistant20100416.pdf
29. Yamashita M, Tomozawa T, Kakuta M, et al. CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity. Antimicrob Agents Chemother 2009; 53:186-192.
30. Kubo S, Tomozawa T, Kakuta M, et al. Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration. Antimicrob Agents Chemother 2010; 54:1256-1264.
31. Koyama K, Takahashi M, Oitate M, et al. CS-8958, a prodrug of the novel neuraminidase inhibitor R-125489, demonstrates a favorable long retention profile in the mouse respiratory tract. Antimicrob Agents Chemother 2009; 53:4845-4851.
32. Koyama K, Takahashi M, Nakai N, et al. Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats. Xenobiotica 2010; 40:207-216.
33. Kiso M, Kubo S, Ozawa M, et al. Efficacy of the new neuraminidase inhibitor CS-8958 against H5N1 influenza viruses. PLoS Pathog 2010; 6:e1000786.
34. Nguyen HT, Sheu TG, Mishin VP, et al. Assessment of pandemic and seasonal influenza A (H1N1) virus susceptibility to neuraminidase inhibitors in three enzyme activity inhibition assays. Antimicrob Agents Chemother 2010; 54:3671-3677.
35. Ishizuka H, Yoshiba S, Okabe H, et al. Clinical pharmacokinetics of laninamivir, a novel long-acting neuraminidase inhibitor, after single and multiple inhaled doses of its prodrug, CS-8958, in healthy male volunteers. J Clin Pharmacol 2010. doi 10.1177/0091270009356297.
36. Sugaya N, Ohashi Y. Long-acting neuraminidase inhibitor laninamivir octanoate (CS-8958) versus oseltamivir as treatment for children with influenza virus infection. Antimicrob Agents Chemother 2010; 54:2575-2582.
37. Daiichi Sankyo Co., Ltd. News Release. Positive top line results from Phase III study (MARVEL) of anti-influenza virus agent CS-8958. (Updated 10 August 2009. Accessed 27 October 2010.) Available from http://www.daiichisankyo. com/news/mt-pdf/news2009-08-10-206-en.pdf
38. Watanabe A, Chang SC, Kim MJ, et al. Long-acting neuraminidase inhibitor laninamivir octanoate versus oseltamivir for treatment of influenza: a double-blind, randomized, noninferiority clinical trial. Clin Infect Dis 2010; 51:1167-1175.
39. Barnett JM, Cadman A, Gor D, et al. Zanamivir susceptibility monitoring and characterization of influenza virus clinical isolates obtained during Phase II clinical efficacy studies. Antimicrob Agents Chemother 2000; 44:78-87.
40. Rogers GN, Paulson JC. Receptor determinants of human and animal influenza virus isolates: differences in receptor specificity of the H3 hemagglutinin based on species of origin. Virology 1983; 127:361-373.
41. Carroll SM, Paulson JC. Differential infection of receptor-modified host cells by receptor-specific influenza viruses. Virus Res 1985; 3:165-179.
42. Govorkova EA, Murti A, Meignier B, de Taisne C, Webster RG. African green monkey kidney (Vero) cells provide an alternative host cell system for influenza A and B viruses. J Virol 1996; 70:5519-5524. (Pubitemid 26240727)
43. Ito T, Suzuki Y, Takada A, et al. Differences in sialic acid-galactose linkages in the chicken egg amnion and allantois influence human influenza virus receptor specificity and variant selection. J Virol 1997; 71:3357-3362.
44. [Japanese regulatory submission document for Tamiflu prophylaxis use by Chugai Pharamceutical Co. Ltd], pp. 79. Japanese. (Updated 22 September 2004. Accessed 27 October 2010.) Available from http://www.info.pmda. go.jp/shinyaku/g040703/index.html
45. Bantia S, Arnold CS, Parker CD, et al. Anti-influenza virus activity of peramivir in mice with single intramuscular injection. Antiviral Res 2006; 69:39-45. (Pubitemid 41790480)
46. Bantia S, Parker CD, Ananth SL, et al. Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir. Antimicrob Agents Chemother 2001; 45:1162-1167.
47. Smee DF, Huffman JH, Morrison AC, et al. Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities. Antimicrob Agents Chemother 2001; 45:743-748.