The electrochemical oxidation of Riluzole, a neuroprotective drug: comparison with the reaction with oxygen derived radicals

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Mehmet A. Oturan, Jean Pinson, Mounir Traikia and Dominique Deprez


Abstract

The electrochemical oxidation of Riluzole, a neuroprotective drug, is investigated. It leads to the formation of an azo dimer through a short lived radical cation. The same dimer is obtained by reaction with dioxygen in the presence of copper or in the presence of superoxide ion. The reaction with electrochemically generated hydroxyl radicals provides two hydroxylated derivatives which have been previously identified as metabolites of Riluzole.


References

  1. G. Bensimon, L. Lacomblez, V. Meininger and the ALS/Riluzole study group, New Engl. J. Med., 1994330585 Search PubMed.
  2. H. M. Bryson, B. Fulton and P. Benfield, Drug, 1996, 52, 549 Search PubMed.
  3. J. Mantz, A. Cheremy, A. M. Thierry, J. Glowinski, D. Jacques and J. M. Desmonts, Anesthesiology, 1992, 76, 844 Search PubMed.
  4. P. Couratier, P. Sindou, F. Esclaire, E. Louvel and J. Hugon, Neuroreport, 1994, 5, 1012 Search PubMed.
  5. P. M. Sinet, La Recherche, 1993, 24, 1028 Search PubMed.
  6. J. M. Stutzmann and A. Doble, Neurodegener. Dis., [Proc. Int. Round Table Rhone-Poulenc Rorer Fund], 1993, pp. 205–214, ed. G. Jolles and J. M. Stutzman, Academic Press, London, 1994 Search PubMed.
  7. D. Martin, M. A. Thompson and J. Nadler, Eur. J. Pharmacol., 1993, 250, 473 CrossRef CAS.
  8. J. Wokke, Lancet, 1996, 348(9030), 795 CrossRef CAS.
  9. D. Garreau and J. M. Savéant, J. Electroanal. Chem., 1972, 35, 309 CrossRef CAS.
  10. C. P. Andrieux, D. Garreau, P. Hapiot, J. Pinson and J. M. Savéant, J. Electroanal. Chem., 1988, 243, 321 CrossRef CAS.
  11. W. G. Nigh, in Oxidation in Organic Chemistry, ed. W. S. Trahanovsky, Academic Press, New York, Part B, 1973, p. 53 Search PubMed.
  12. R. N. Goyal, A. Minocha and A. P. Nautiyal, J. Electroanal. Chem., 1986, 200, 119 CrossRef CAS.
  13. W. U. Malik, R. N. Goyal and Rashewari, Bull. Soc. Chim. Fr., 1987, 791 CAS.
  14. G. Cauquis, H. M. Fahmy, G. Pierre and M. H. Elnagdi, J. Heterocycl. Chem., 1979, 16, 413 CAS.
  15. G. Cauquis, H. M. Fahmy, G. Pierre and M. H. Elnagdi, Electrochim. Acta, 1979, 24, 391 CrossRef CAS.
  16. G. Van Koten, S. L. James and J. T. B. H. Jastrzebski, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon Press, Oxford, vol. 3, 1995, pp. 92 and 127 Search PubMed.
  17. B. J. Hathaway, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McClaverty, Pergamon Press, Oxford, vol. 5, 1987, pp. 553–773 Search PubMed.
  18. M. R. Grimmett, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, vol. 5, 1984, p. 386 Search PubMed.
  19. M. A. Oturan, J. Pinson, J. Bizot, D. Deprez and B. Terlain, J. Electroanal. Chem., 1992, 334, 103 CrossRef CAS.
  20. M. A. Oturan, J. Pinson, D. Deprez and B. Terlain, New J. Chem., 1992, 16, 705 Search PubMed.
  21. M. A. Oturan and J. Pinson, J. Phys. Chem., 1995, 99, 13 948 CrossRef CAS.
  22. D. T. Sawyer and J. S. Valentine, Acc. Chem. Res., 1981, 14, 393 CrossRef CAS.
  23. M. Gareil, J. Pinson and J. M. Savéant, Nouv. J. Chim., 1981, 5, 311 Search PubMed.
  24. M. A. Oturan, J. Moiroux, M. B. Fleury and P. Dostert, J. Electroanal. Chem., 1988, 272, 171 CrossRef.
  25. E. J. Nanni, M. D. Stallings and D. T. Sawyer, J. Am. Chem. Soc., 1980, 102, 4481 CrossRef CAS.
  26. E. J. Nanni and D. T. Sawyer, J. Am. Chem. Soc., 1980, 102, 7593 CrossRef CAS.
  27. G. Crank and M. I. H. Makin, Aust. J. Chem., 1984, 37, 845 CAS.