Nuclear Medicine and Biology
Volume 36, Issue 1 , Pages 47-55 , January 2009

Biodistribution and metabolism of the anti-influenza drug [11C]oseltamivir and its active metabolite [11C]Ro 64-0802 in mice

Received 22 July 2008 ,Revised 10 October 2008 ,Accepted 15 October 2008.

References 

  1. Kim CU, Lew W, Williams MA, Liu H, Zhang L, Swaminathan S, et al. Influenza neuraminidase inhibitor possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity. J Am Chem Soc. 1997;119:681–690
  2. Calfee DP, Hayden FG. New approaches to influenza chemotherapy. Neuraminidase inhibitors. Drugs. 1998;56:537–553
  3. Kim CU, Chen X, Mendel DB. Neuraminidase inhibitors as anti-influenza virus agents. Antivir Chem Chemother. 1999;10:141–154
  4. Eisenberg EJ, Bidgood A, Cundy KC. Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104. Antimicrob Agents Chemother. 1997;41:1949–1952
  5. Li W, Escarpe PA, Eisenberg EJ, Cundy KC, Sweet C, Kakeman KJ, et al. Identification of GS 4104 as an orally bioavailable prodrug of the influenza virus neuraminidase inhibitor GS 4071. Antimicrob Agents Chemother. 1998;42:647–653
  6. He J, Massarella P, Ward P. Clinical pharmacokinetics of the prodrug oseltamivir and its active metabolite Ro 64-0802. Clin Pharmacokinet. 1999;37:471–484
  7. (a) http://www.nature.com/news/2007/070319/full/446358a.html. (b) http://www.forbes.com/feeds/ap/2007/04/04/ap3582952.html.
  8. http://www.mhlw.go.jp/shingi/2007/12/2/1225-7.html.
  9. Rodriguez JA, Piddini E, Hasegawa T, Miyagi T, Dotti CG. Plasma membrane ganglioside sialidase regulates axonal growth and regeneration in hippocampal neurons in culture. J Neurosci. 2001;21:8387–8395
  10. Crain SM, Shen KF. Neuraminidase inhibitor, oseltamivir blocks GM1 ganglioside-regulated excitatory opioid receptor-mediated hyperalgesia, enhances opioid analgesia and attenuates tolerance in mice. Brain Res. 2004;995:260–266
  11. Ono H, Nagano Y, Matsunami N, Sugiyama S, Yamamoto S, Tanabe M. Oseltamivir, an anti-influenza virus drug, produces hypothermia in mice. Biol Pharm Bull. 2008;31:638–642
  12. Izumi Y, Tokuda K, O'dell KA, Zorumski CF, Narahashi T. Neuroexcitatory actions of Tamiflu and its carboxylate metabolite. Neurosci Lett. 2007;426:54–58
  13. Usami A, Sasaki T, Satoh N, Akiba T, Yokoshima S, Fukuyama T, et al. Oseltamivir enhances hippocampal network synchronization. J Pharmacol Sci. 2008;106:659–662
  14. http://www.fda.gov/cder/foi/label/2006/021087s0331b1.pdf.
  15. Dutkowski R, Thakrar B, Froehlich E, Suter P, Oo C, Ward P. Safety and pharmacology of oseltamivir in clinical use. Drug Saf. 2003;26:787–801
  16. Blumentals WA, Song X. The safety of oseltamivir in patients with influenza: analysis of healthcare claims data from six influenza seasons. Med GenMed. 2007;9:23
  17. Okamoto S, Kamiya M, Kishida K, Shimakawa T, Fukui T, Morimoro T. Experience with oseltamivir for infants younger than 1 year old in Japan. Pediatr Infect Dis J. 2005;24:575–576
  18. Hama R. Oseltamivir's adverse reactions: fifty sudden deaths may be related to central suppression. BMJ. 2007;335:59
  19. Fowler JS, Volkow ND, Wang GJ, Ding YS, Dewey SL. PET and drug research and development. J Nucl Med. 1999;4:1154–1163
  20. Whitley RJ. The role of oseltamivir in the treatment and prevention of influenza in children. Expert Opin Drug Metab Toxicol. 2007;3:755–767
  21. Crusat M, de Jong MD. Neuraminidase inhibitors and their role in avian and pandemic influenza. Antivir Ther. 2007;12:593–602
  22. Konno F, Arai T, Zhang MR, Hatori A, Yanamoto K, Ogawa M, et al. Radiosynthesis of two positron emission tomography probes: [11C]oseltamivir and its active metabolite [11C]Ro 64-0802. Bioorg Med Chem Lett. 2008;18:1260–1263
  23. Le Bars D, Luthra SK, Pike VW, Luu Duc C. The preparation of a carbon-11 labelled neurohormone—[11C]melatonin. Appl Radiat Isot. 1987;38:1073–1077
  24. Arai T, Zhang MR, Ogawa M, Fukumura T, Kato K, Suzuki K. Efficient and reproducible synthesis of [1-11C]acetyl chloride using the loop method. Appl Rad Isot. 2008;[doi:10.1016/j.apradiso.2008.09.013]
  25. Zhang MR, Kida T, Noguchi J, Furutsuka K, Maeda M, Suhara T, et al. [11C]DAA1106: radiosynthesis and in vivo binding to peripheral benzodiazepine receptors in mouse brain. Nucl Med Biol. 2003;30:513–519
  26. Zhang MR, Maeda J, Ogawa M, Noguchi J, Ito T, Yoshida Y, et al. Development of a new radioligand, N-(5-fluoro-2-phenoxyphenyl)-N-(2-[18F]fluoroethyl-5-methoxybenzyl)acetamide, for PET imaging of peripheral benzodiazepine receptor in primate brain. J Med Chem. 2004;47:2228–2235
  27. Zhang MR, Kumata K, Maeda J, Yanamoto K, Hatori A, Okada M, et al. [11C]AC-5216: a novel positron emission tomography ligand for peripheral-type benzodiazepine receptors in primate brain. J Nucl Med. 2007;48:1853–1861
  28. Morimoto K, Nakakariya M, Shirasaka Y, Kakinuma C, Fujita T, Tamai I, et al. Oseltamivir (Tamiflu) efflux transport at the blood–brain barrier via P-glycoprotein. Drug Metab Dispos. 2008;36:6–9
  29. Ose A, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Fujita T, et al. P-glycoprotein restricts the penetration of oseltamivir across the blood–brain barrier. Drug Metab Dispos. 2008;36:427–434
  30. Sweeny DJ, Lynch G, Bidgood AM, Lew W, Wang KY, Cundy KC. Metabolism of the influenza neuraminidase inhibitor prodrug oseltamivir in the rat. Drug Metab Dispos. 2000;28:737–741
  31. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, et al. Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther. 2006;319:1477–1484
  32. Stewart PA, Hayagawa EM, Carlen PL. Ethanol and pentobarbital in combination increase blood–brain barrier permeability to horseradish peroxidase. Brain Res. 1998;443:12–20

PII: S0969-8051(08)00230-8

doi: 10.1016/j.nucmedbio.2008.10.008

Nuclear Medicine and Biology
Volume 36, Issue 1 , Pages 47-55 , January 2009

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