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Complexation of the Non-steroidal Anti-inflammatory Drug Nabumetone with Modified and Unmodified Cyclodextrins

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Abstract

The inclusion of the anti-inflammatory drug, Nabumetone, in α-, β- and hydroxypropyl-β-cyclodextrin (CDs) is studied using UV-VIS absorption and steady-state fluorescence emission. Binding constants and thermodynamic parameters of complex formation are determined by spectrofluorimetry. The inclusion phenomena of Nabumetone with the three cyclodextrins is compared with that of the well known similar anti-inflammatory drug Naproxen. In the case of Nabumetone pronounced differences are observed in the complexation process with each cyclodextrin whereas the respective Naproxen complexes are nearly identical. 1H-NMR experiments show that the inclusion process in Nabumetone can occur either through the substituents in the -2 (butanone) or -6 (methoxy) positions in the naphthalene ring.

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References

  1. W. Saenger: Angew. Chem., Int. Ed. Engl. 19, 344 (1980).

    Google Scholar 

  2. J. Szejtli: Cyclodextrins and Their Inclusion Complexes, Akademio Kaido, Budapest (1982).

    Google Scholar 

  3. H. Yang and C. Bohne: J. Photochem. Photobiol. A: Chem. 86, 209 (1995).

    Google Scholar 

  4. A. V. Eliseev, G. A. Lacobucci, N. A. Khanjin, and F. M Menger: J. Chem. Soc., Chem. Commun. 2051 (1994).

  5. G. H. Coates, C. J. Easton, S. J. van Eyk, B. L. May, P. Singh, and S. F. Lincoln: J. Chem. Soc., Chem. Commun. 759 (1991).

  6. K. Minami, F. Hirayama, and K. Uekama: J. Pharm. Sci. 87, 715 (1998).

    Google Scholar 

  7. M. Kata, Z. Aigner, and I. Eros: Acta Pharm. Hung. 68, 107 (1998).

    Google Scholar 

  8. A. Donelly, I. W. Kellaway, G. Taylor, and M. Gibson: J. Drug Target 5, 121 (1998).

    Google Scholar 

  9. A. Badwan, A. Abumalooh, M. Haddadin, and H. Ibrahim: (Arab Company for Drug Industries and Medical Applicances (ACDIMA) Jordan) U.S. US 5, 646, 131 (Cl. 514-58; A61k31/715), 8 Jul 1997, US Appl. 199, 523, 22 Feb; Cont of U.S. Ser. No. 199, 523 (1994).

  10. J. Szejtli and L. Szente: Pharmazie 36, 694 (1985).

    Google Scholar 

  11. M. Catzola, F. Montrone, G. Vaiani, and I. Carwo: Drugs 40, 78 (1990).

    Google Scholar 

  12. I. Stroehmann, M. Fedder, and H. Zeidler: Drugs 40, 38 (1990).

    Google Scholar 

  13. G. Vaiani and E. Grossi: Drugs 40, 48 (1990).

    Google Scholar 

  14. Y. Habon, S. Fritsch, and J. Szejtli: Pharmazie 39, 830 (1984).

    Google Scholar 

  15. E. S. Brown, J. H. Coates, C. J. Easton, S. F. Lincoln, Y. Luo, and A. K. W. Stephens: Aust. J. Chem. 44, 855 (1991).

    Google Scholar 

  16. M. Valero, L. J. Rodríguez, and M. M. Velázquez: Il Farmaco 51, 525 (1996).

    Google Scholar 

  17. A. Ashnagar, P. T. Culane, C. J. Easton, J. B. Harper, and S. F. Lincoln: Aust. J. Chem. 50, 447 (1997).

    Google Scholar 

  18. S. E. Brown, J. H. Coates, D. R. Coghan, C. J. Easton, S. J. van Eyk, W. Janowski, A. Lepore, S. F. Lincoln, Y. Luo, B. L. May, D. S. Schiesser, P. Wang, and M. L. Williams: Aust. J. Chem. 46, 953 (1993).

    Google Scholar 

  19. M. Valero: Doctoral Thesis., Salamanca University (1994).

  20. G. Bettineti, F. Melani, P. Mura, R. Monnanni, and F. Giordano: J. Pharm. Sci. 80, 1162 (1991).

    Google Scholar 

  21. M. M. Velázquez, M. Valero, L. J. Rodríguez, S. M. B. Costa, and M. A. Santos: J. Photochem. Photobiol. B: Biol. 29, 23 (1995).

    Google Scholar 

  22. I. Tabushi: Acc. Chem. Res. 15, 66 (1982).

    Google Scholar 

  23. R. J. Clarke, J. H. Coates, and S. F. Lincoln: Adv. Carbohydr. Chem. Biochem. 46, 205 (1988).

    Google Scholar 

  24. O. S. Tee, A. A. Fedortchenki, P. G. Loncke, and T. A. Gadosy: J. Chem. Soc., Perkin Trans. 2, 1243 (1996).

    Google Scholar 

  25. E. A. Lewis and L. D. Hansen: J. Chem. Soc. Perkin Trans. 2 2081 (1973).

  26. W. Linert, L. Han, and I. Lukovits: Chem. Phys. 139, 441 (1989).

    Google Scholar 

  27. Y. Inoue, T. Hakushi, Y. Liu, L. H. Tong, B. J. Shen, and D. S. Jin: J.Am.Chem.Soc. 115, 475 (1993).

    Google Scholar 

  28. R. I. Gelb and J. S. Alper: J. Phys. Org. Chem. 8, 825 (1995).

    Google Scholar 

  29. K. A. Connors: Chem. Rev. 97, 1325 (1997).

    Google Scholar 

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Valero, M., Costa, S.M.B., Ascenso, J.R. et al. Complexation of the Non-steroidal Anti-inflammatory Drug Nabumetone with Modified and Unmodified Cyclodextrins. Journal of Inclusion Phenomena 35, 663–677 (1999). https://doi.org/10.1023/A:1008011228459

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  • DOI: https://doi.org/10.1023/A:1008011228459

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