Pharmacokinetic mechanism involved in the prolonged high retention of laninamivir in mouse respiratory tissues after intranasal administration of its prodrug laninamivir octanoate

Drug Metabolism and Disposition

Volumn 41, Issue 1, 2013, Pages 180-187

  Koyama, Kumiko ^a   Nakai, Daisuke ^a   Takahashi, Makoto ^a   Nakai, Naoko ^a   Kobayashi, Nobuhiro ^a   Imai, Teruko ^b   Izumi, Takashi ^a  

^a DAIICHI SANKYO CO   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; ESTERASE; LANINAMIVIR; LANINAMIVIR OCTANOATE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; CELL TRANSPORT; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG RELEASE; EPITHELIUM CELL; FEMALE; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; MEMBRANE PERMEABILITY; MICRORADIOGRAPHY; MOUSE; NONHUMAN; PRIORITY JOURNAL; TIME TO MAXIMUM PLASMA CONCENTRATION;

ADMINISTRATION, INTRANASAL; ANIMALS; AUTORADIOGRAPHY; CELLS, CULTURED; ENZYME INHIBITORS; LUNG; MICE; MICE, INBRED BALB C; NEURAMINIDASE; PRODRUGS; TRACHEA; ZANAMIVIR;

MUS;

EID: 84871593477     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.048280     Document Type: Article

References (34)

1. Baldwin DR, Honeybourne D, and Wise R (1992) Pulmonary disposition of antimicrobial agents: methodological considerations. Antimicrob Agents Chemother 36:1171-1175.
2. Bodor N, Farag HH, Barros MD, Wu WM, and Buchwald P (2002) In vitro and in vivo evaluations of dihydroquinoline- and dihydroisoquinoline-based targetor moieties for brain-specific chemical delivery systems. J Drug Target 10:63-71. (Pubitemid 34223851)
3. Brown RA, Jr and Schanker LS (1983) Absorption of aerosolized drugs from the rat lung. Drug Metab Dispos 11:355-360.
4. Effros RM and Mason GR (1983) Measurements of pulmonary epithelial permeability in vivo. Am Rev Respir Dis 127:S59-S65. (Pubitemid 13103650)
5. de Lannoy IA and Pang KS (1986) Presence of a diffusional barrier on metabolite kinetics: enalaprilat as a generated versus preformed metabolite. Drug Metab Dispos 14:513-520.
6. Hastings RH, Grady M, Sakuma T, and Matthay MA (1992) Clearance of different-sized proteins from the alveolar space in humans and rabbits. J Appl Physiol 73:1310-1316.
7. Honda T, Kubo S, Masuda T, Arai M, Kobayashi Y, and Yamashita M (2009) Synthesis and in vivo influenza virus-inhibitory effect of ester prodrug of 4-guanidino-7-O-methyl-Neu5Ac2en. Bioorg Med Chem Lett 19:2938-2940.
8. Ishizuka H, Toyama K, Yoshiba S, Okabe H, and Furuie H (2012) Intrapulmonary distribution and pharmacokinetics of laninamivir, a neuraminidase inhibitor, after a single inhaled administration of its prodrug, laninamivir octanoate, in healthy volunteers. Antimicrob Agents Chemother 56:3873-3878.
9. Ishizuka H, Yoshiba S, Okabe H, and Yoshihara K (2010) Clinical pharmacokinetics of R-125489, a novel long-acting neuraminidase inhibitor, after single and multiple inhaled doses of its prodrug, CS-8958, in healthy male volunteers. J Clin Pharmacol 50:1319-1329.
10. Itoh Y, Shinya K, and Kiso M, et al. (2009) In vitro and in vivo characterization of new swine-origin H1N1 influenza viruses. Nature 460:1021-1025.
11. Kiso M, Kubo S, Ozawa M, Le QM, Nidom CA, Yamashita M, and Kawaoka Y (2010) Efficacy of the new neuraminidase inhibitor CS-8958 against H5N1 influenza viruses. PLoS Pathog 6:e1000786.
12. Koyama K, Takahashi M, Nakai N, Takakusa H, Murai T, Hoshi M, Yamamura N, Kobayashi N, and Okazaki O (2010) Pharmacokinetics and disposition of CS-8958, a long-acting prodrug of the novel neuraminidase inhibitor laninamivir in rats. Xenobiotica 40:207-216.
13. Koyama K, Takahashi M, Oitate M, Nakai N, Takakusa H, Miura SI, and Okazaki O (2009) 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 53:4845-4851.
14. Kubo S, Tomozawa T, Kakuta M, Tokumitsu A, and Yamashita M (2010) Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration. Antimicrob Agents Chemother 54:1256-1264.
15. Kumari M and Saxena RK (2011) Relative efficacy of uptake and presentation of Mycobacterium bovis BCG antigens by type I mouse lung epithelial cells and peritoneal macrophages. Infect Immun 79:3159-3167.
16. Matsukawa Y, Lee VH, Crandall ED, and Kim KJ (1997) Size-dependent dextran transport across rat alveolar epithelial cell monolayers. J Pharm Sci 86:305-309. (Pubitemid 27113763)
17. Nave R, Watz H, Hoffmann H, Boss H, and Magnussen H (2010) Deposition and metabolism of inhaled ciclesonide in the human lung. Eur Respir J 36:1113-1119.
18. Pang KS, Cherry WF, Terrell JA, and Ulm EH (1984) Disposition of enalapril and its diacid metabolite, enalaprilat, in a perfused rat liver preparation. Presence of a diffusional barrier for enalaprilat into hepatocytes. Drug Metab Dispos 12:309-313. (Pubitemid 15120549)
19. Patton JS (1996) Mechanisms of macromolecule absorption by the lungs. Adv Drug Deliv Rev 19:3-36.
20. Prokai L, Prokai-Tatrai K, Ouyang X, Kim HS, Wu WM, Zharikova A, and Bodor N (1999) Metabolism-based brain-targeting system for a thyrotropin-releasing hormone analogue. J Med Chem 42:4563-4571. (Pubitemid 29530010)
21. Rennard SI, Basset G, Lecossier D, O'Donnell KM, Pinkston P, Martin PG, and Crystal RG (1986) Estimation of volume of epithelial lining fluid recovered by lavage using urea as marker of dilution. J Appl Physiol 60:532-538. (Pubitemid 16019939)
22. Rodvold KA, George JM, and Yoo L (2011a) Penetration of anti-infective agents into pulmonary epithelial lining fluid: focus on antibacterial agents. Clin Pharmacokinet 50:637-664.
23. Rodvold KA, Yoo L, and George JM (2011b) Penetration of anti-infective agents into pulmonary epithelial lining fluid: focus on antifungal, antitubercular and miscellaneous anti-infective agents. Clin Pharmacokinet 50:689-704.
24. Schanker LS and Hemberger JA (1983) Relation between molecular weight and pulmonary absorption rate of lipid-insoluble compounds in neonatal and adult rats. Biochem Pharmacol 32:2599-2601. (Pubitemid 13007874)
25. Schneeberger EE (1991) Airway and alveolar epithelia cell junctions, in The Lung: Scientific Foundations (Crystal RG, West JB, Barnes PJ, Cherniack NS, and Weibel ER, eds) pp 205-214, Raven Press, New York.
26. Somers GI, Lindsay N, Lowdon BM, Jones AE, Freathy C, Ho S, Woodrooffe AJ, Bayliss MK, and Manchee GR (2007) A comparison of the expression and metabolizing activities of phase I and II enzymes in freshly isolated human lung parenchymal cells and cryopreserved human hepatocytes. Drug Metab Dispos 35:1797-1805. (Pubitemid 47481571)
27. Sugaya N and Ohashi Y (2010) Long-acting neuraminidase inhibitor laninamivir octanoate (CS-8958) versus oseltamivir as treatment for children with influenza virus infection. Antimicrob Agents Chemother 54:2575-2582.
28. Tapfer MK, Sebestyen L, Kurucz I, Horvath K, Szelenyi I, and Bodor N (2004) New evidence for the selective, long-lasting central effects of the brain-targeted estradiol, Estredox. Pharmacol Biochem Behav 77:423-429. (Pubitemid 38296801)
29. Tronde A, Nordén B, Jeppsson AB, Brunmark P, Nilsson E, Lennernäs H, and Bengtsson UH (2003) Drug absorption from the isolated perfused rat lung - correlations with drug physicochemical properties and epithelial permeability. J Drug Target 11:61-74. (Pubitemid 36527397)
30. Watanabe A, Chang SC, Kim MJ, Chu DW, and Ohashi Y; MARVEL Study Group (2010) Long-acting neuraminidase inhibitor laninamivir octanoate versus oseltamivir for treatment of influenza: A double-blind, randomized, noninferiority clinical trial. Clin Infect Dis 51:1167-1175.
31. Würthwein G and Rohdewald P (1990) Activation of beclomethasone dipropionate by hydrolysis to beclomethasone-17-monopropionate. Biopharm Drug Dispos 11:381-394. (Pubitemid 20247808)
32. Yamashita M, Tomozawa T, Kakuta M, Tokumitsu A, Nasu H, and Kubo S (2009) CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity. Antimicrob Agents Chemother 53:186-192.
33. Yoshiba S, Okabe H, and Ishizuka H (2011) Pharmacokinetics of laninamivir after a single administration of its prodrug, laninamivir octanoate, a long-acting neuraminidase inhibitor, using an easy-to-use inhaler in healthy volunteers. J Bioequiv Availab 3:1-4.
34. Zhang JY, Wang Y, and Prakash C (2006) Xenobiotic-metabolizing enzymes in human lung. Curr Drug Metab 7:939-948. (Pubitemid 44873716)