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
W. Saenger: Angew. Chem., Int. Ed. Engl. 19, 344 (1980).
J. Szejtli: Cyclodextrins and Their Inclusion Complexes, Akademio Kaido, Budapest (1982).
H. Yang and C. Bohne: J. Photochem. Photobiol. A: Chem. 86, 209 (1995).
A. V. Eliseev, G. A. Lacobucci, N. A. Khanjin, and F. M Menger: J. Chem. Soc., Chem. Commun. 2051 (1994).
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).
K. Minami, F. Hirayama, and K. Uekama: J. Pharm. Sci. 87, 715 (1998).
M. Kata, Z. Aigner, and I. Eros: Acta Pharm. Hung. 68, 107 (1998).
A. Donelly, I. W. Kellaway, G. Taylor, and M. Gibson: J. Drug Target 5, 121 (1998).
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).
J. Szejtli and L. Szente: Pharmazie 36, 694 (1985).
M. Catzola, F. Montrone, G. Vaiani, and I. Carwo: Drugs 40, 78 (1990).
I. Stroehmann, M. Fedder, and H. Zeidler: Drugs 40, 38 (1990).
G. Vaiani and E. Grossi: Drugs 40, 48 (1990).
Y. Habon, S. Fritsch, and J. Szejtli: Pharmazie 39, 830 (1984).
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).
M. Valero, L. J. Rodríguez, and M. M. Velázquez: Il Farmaco 51, 525 (1996).
A. Ashnagar, P. T. Culane, C. J. Easton, J. B. Harper, and S. F. Lincoln: Aust. J. Chem. 50, 447 (1997).
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).
M. Valero: Doctoral Thesis., Salamanca University (1994).
G. Bettineti, F. Melani, P. Mura, R. Monnanni, and F. Giordano: J. Pharm. Sci. 80, 1162 (1991).
M. M. Velázquez, M. Valero, L. J. Rodríguez, S. M. B. Costa, and M. A. Santos: J. Photochem. Photobiol. B: Biol. 29, 23 (1995).
I. Tabushi: Acc. Chem. Res. 15, 66 (1982).
R. J. Clarke, J. H. Coates, and S. F. Lincoln: Adv. Carbohydr. Chem. Biochem. 46, 205 (1988).
O. S. Tee, A. A. Fedortchenki, P. G. Loncke, and T. A. Gadosy: J. Chem. Soc., Perkin Trans. 2, 1243 (1996).
E. A. Lewis and L. D. Hansen: J. Chem. Soc. Perkin Trans. 2 2081 (1973).
W. Linert, L. Han, and I. Lukovits: Chem. Phys. 139, 441 (1989).
Y. Inoue, T. Hakushi, Y. Liu, L. H. Tong, B. J. Shen, and D. S. Jin: J.Am.Chem.Soc. 115, 475 (1993).
R. I. Gelb and J. S. Alper: J. Phys. Org. Chem. 8, 825 (1995).
K. A. Connors: Chem. Rev. 97, 1325 (1997).
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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