A fluorimetric, potentiometric and conductimetric study of the aqueous solutions of naproxen and its association with hydroxypropyl-β-cyclodextrin

International Journal of Pharmaceutics

Volumn 176, Issue 2, 1999, Pages 169-178

  Junquera, E ^a   Aicart, E ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Association constant; Conductimetry; Fluorescence; Hydroxypropyl cyclodextrin; Inclusion complex; Naproxen; Potentiometry

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; NAPROXEN;

ACCURACY; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONDUCTOMETRY; DRUG DETERMINATION; DRUG SOLUBILITY; FLUOROMETRY; IN VITRO STUDY; PH; POTENTIOMETRY; PRIORITY JOURNAL;

EID: 0032963089     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(98)00313-5     Document Type: Article

References (31)

1. Bergeron R.J., Channing M.A., McGovern K.A. Dependence of cycloamylose-substrate binding on charge. J. Am. Chem. Soc. 100:1978;2878-2883.
2. Bettinetti G.P., Mura P., Liguori A., Bramanti G. Solubilization and interaction of naproxen with cyclodextrins in aqueous solution and in the solid state. Il Farmaco. 2:1989;195-213.
3. Bettinetti G.P., Melani F., Mura P., Monnanni R., Giordano F. Carbon-13 nuclear magnetic resonance study of naproxen interaction with cyclodextrins in solution. J. Pharm. Sci. 80:1991;1162-1170.
4. Bettinetti G.P., Mura P., Melani F., Rollosi M., Giordano F. Interactions between naproxen and maltoheptaose, the non-cyclic analog of β-cyclodextrin. J. Incl. Phenom. 25:1996;327-338.
5. Brown S.E., Coates J.H., Easton C.J., Lincoln S.F., Luo Y., Stephens K.W. Cyclodextrin inclusion complexes of two non-steroidal antiiflammatory drugs and of an analgesic drug. Aust. J. Chem. 44:1991;855-862.
6. Calvo M.V., Lanao J.M., Domínguez-Gil A. Bioavailability of rectally administered naproxen. Int. J. Pharm. 38:1987;117-122.
7. Chowhan Z.T. pH-Solubility profiles of organic carboxylic acids and their salts. J. Pharm. Sci. 67:1978;1257-1260.
8. Connors, K.A., 1987. Binding Constants: The Measurement of Molecular Complex Stability. Wiley, New York.
9. Connors K.A. The stability of cyclodextrin complexes in solution. Chem. Rev. 97:1997;1325-1357.
10. Cromwell W.C., Bystrom K., Eftink M.R. Cyclodextrin-adamantanecarboxylate inclusion complexes: studies of the variation in cavity size. J. Phys. Chem. 89:1985;326-332.
11. De Guidi G., Condorelli G., Giuffrida S., Puglisi G., Giammona G. Effect of β-cyclodextrin complexation on the photohaemolitic activity induced by ketoprophen and naproxen sensitization. J. Incl. Phenom. 15:1993;43-58.
12. Deranleau D.A. Theory of measurement of weak molecular complexes. I. General considerations. J. Am. Chem. Soc. 91:1969;4044-4049.
13. Erden N., Çelebi N. A study of the inclusion complex of naproxen with β-cyclodextrin. Int. J. Pharm. 48:1988;83-89.
14. Gelb R.I., Schwartz L.M., Johnson R.F., Laufer D.A. The complexation chemistry of cyclohexaamyloses. 4. Reactions of cyclohexaamylose with formic, acetic, and benzoic acids and their conjugate bases. J. Am. Chem. Soc. 101:1979;1869-1874.
15. Gelb R.I., Schwartz L.M., Cardelino B., Fuhrman H.S., Johnson R.F., Laufer D.A. Binding mechanisms in cyclohexaamylose complexes. J. Am. Chem. Soc. 103:1981;1750-1757.
16. Herzfeldt C.D., Kuemmel R. Dissociation constants, solubility and dissolution rates of some selected nonsteroidal antiinflammatories. Drug Dev. Ind. Pharm. 9:1983;767-793.
17. Junquera E., Aicart E. A fully computerized technique to measure conductivity in liquid mixtures. Rev. Sci. Instrum. 65:1994;2672-2674.
18. Junquera E., Aicart E. Effect of pH on the encapsulation of the salicylic acid/salicylate system by hydroxypropyl-β-cyclodextrin at 25°C. A fluorescence enhancement study in aqueous solutions. J. Incl. Phenom. 29:1997;119-136.
19. Junquera E., Aicart E. Potentiometric study of the encapsulation of ketoprophen by hydroxypropyl-β-cyclodextrin. Temperature, solvent and salt effects. J. Phys. Chem. B. 101:1997;7163-7171.
20. Junquera E., Peña L., Aicart E. Binding of sodium salicylate by β-cyclodextrin or 2,6-di-O-methyl-β-cyclodextrin in aqueous solution. J. Pharm. Sci. 87:1998;86-90.
21. Junquera E., Aicart E. Molecular encapsulation of flurbiprophen and/or ibuprophen by hydroxypropyl-β-cyclodextrin in aqueous solution. Potentiometric and molecular modelling studies. J. Org. Chem. 63:1998;4349-4358.
22. Mahler D.L., Forrest W.H., Brown C.R., Shroft P.F., Gordon H.E., Brown B.W., James K.E. Assay of aspirin and naproxen analgesia. Clin. Pharmacol. Ther. 19:1976;18-22.
23. Martin-Davies D., Savage J.S. Cyclodextrin complexes of substituted perbenzoic and benzoic acids and their conjugate bases: free energy relationships show the interaction of polar and steric factors. J. Chem. Soc. Perkin Trans. 2:1994;1525-1530.
24. McNamara D.P., Amidon G.L. Dissolution of acidic and basic compounds from the rotating disk: influence of convective diffusion and reaction. J. Pharm. Sci. 75:1986;858-868.
25. Melani F., Bettinetti G.P., Mura P., Manderioli A. Interaction of naproxen with α-, β-, and γ-hydroxypropyl cyclodextrins in solution and in the solid state. J. Incl. Phenom. 22:1995;131-143.
26. Orienti I., Fini A., Bertasi V., Zecchi V. Inclusion complexes between non-steroidal antiinflammatory drugs and β-cyclodextrin. Eur. J. Pharm. Biopharm. 37:1991;110-112.
27. Otero-Espinar F.J., Anguiano-Igea S., García-González N., Vila-Jato J.L., Blanco-Méndez J. Interaction of naproxen with β-cyclodextrin in solution and in the solid state. Int. J. Pharm. 79:1992;149-157.
28. Szejtli, J. and Osa, T., 1996. Comprehensive Supramolecular Chemistry, vol. 3, Cyclodextrins. Oxford, Elsevier.
29. Valsami G.N., Macheras P.E., Koupparis M. Binding studies of ions with cyclodextrins using ion-selective electrodes. J. Pharm. Sci. 79:1990;1087-1094.
30. Vélaz I., Sánchez M., Martín C., Martínez-Ohárriz M.C., Zornoza A. Interactions of naproxen with vinylpyrrolidone and β-cyclodextrin: a fluorimetric study. Int. J. Pharm. 153:1997;211-217.
31. Zecchi V., Orienti I., Fini A. Chemical properties-dissolution relationship of NSAIDs. Release from monoliths in a three phase system. Pharm. Acta Helv. 63:1988;299-302.