Ternary systems of naproxen with hydroxypropyl-β-cyclodextrin and aminoacids

International Journal of Pharmaceutics

Volumn 260, Issue 2, 2003, Pages 293-302

  Mura, Paola ^a   Maestrelli, Francesca ^a   Cirri, Marzia ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Aminoacids; Arginine; Hydroxypropyl cyclodextrin; Multicomponent complexes; Naproxen; Solubilization

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; AMINO ACID; ARGININE; BUFFER; ISOLEUCINE; LYSINE; NAPROXEN; VALINE;

AMINO ACID SUBSTITUTION; AQUEOUS SOLUTION; ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; HOT STAGE MICROSCOPY; MICROSCOPY; PH; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY;

EID: 0038121683     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(03)00265-5     Document Type: Article

References (26)

1. Amidon G., Lennernas H., Shah V., Crison J. A theoretical basis for a biopharmaceutical drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res. 12:1995;413-420.
2. Bao-Yun X., Wen-Sheng C., Xue-Guang S., Qing-Xiang G., Maigret B., Zhong-Xiao P. Chiral recognition for the inclusion complexes of aminoacids with α-cyclodextrin using a fast annealing evolutionary algorithm. J. Mol. Struct. 546:2001;33-38.
3. Berge S., Bighley L.D., Monkhouse D.C. Pharmaceutical salts. J. Pharm. Sci. 66:1977;1-19.
4. Duchêne, D., 1987. In: Cyclodextrin and their Industrial Uses, Ed. de Santè, Paris.
5. Ganzerli G., van Santvliet L., Verschuren E., Ludwig A. Influence of beta-cyclodextrin and various polysaccharides on the solubility of fluorescein and on the rheological and mucoadhesive properties of ophtalmic solutions. Pharmazie. 51:1996;357-362.
6. Higuchi T., Connors K. Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4:1965;117-212.
7. Krishnamoorthy R., Mitra A.K. Complexation of weak acids and bases with cyclodextrins: effects of substrate ionization on the estimation and interpretation of association constants. Int. J. Pharm. Adv. 1:1996;330-343.
8. Laveneziana D., Speranza R., Raulli P., Paredi G. Ibuprofen-arginine in the management of pain. Clin. Drug. Invest. 11:1996;1-7.
9. Li P., Zhao L., Yalkowsky S.H. Combined effect of cosolvent and cyclodextrin on solubilization of nonpolar drugs. J. Pharm. Sci. 88:1999;1107-1111.
10. Loftsson T., Brewster M. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85:1996;1017-1025.
11. Loftsson T., Olafsdottir B., Frioriksdottir H., Jònsdòttir S. Cyclodextrin complexation of NSAIDs: physicochemical characteristics. Eur. J. Pharm. Sci. 1:1993;95-101.
12. Loftsson T., Fridriksdóttir H., Sigurdardóttir A.M., Ueda H. The effect of water-soluble polymers on drug-cyclodextrin complexation. Int. J. Pharm. 110:1994;169-177.
13. Loftsson T., Gudmundsdóttir T.K., Fridriksdóttir F. The influence of water-soluble polymers and pH on hydroxypropyl-βcyclodextrin complexation of drugs. Drug Dev. Ind. Pharm. 22:1996;401-405.
14. Moore E., Bergamo R., Casella R. Direct compression tablets containing a series of four beta-cyclodextrin complexes formed by neutralizing an acidic drug. Drug Dev. Ind. Pharm. 26:2000;1259-1270.
15. Morris K.R., Fakes M.G., Thakur A.B., Newman A.W., Singh A.K., Venit J.J., Spagnuolo C.J., Serajuddin A.T.M. An integrated approach to the selection of optimal salt form for a new drug candidate. Int. J. Pharm. 105:1994;209-217.
16. Muñoz de la Pena A., Ndou T.T., Zung J.B., Greene K.L., Live D.H., Warner I.M. Alcohol size as a factor in the ternary complexes formed with pyrene and βcyclodextrin. J. Am. Chem. Soc. 113:1991;1572-1577.
17. Mura P., Bettinetti G.P., Melani F., Manderioli A. Interaction between naproxen and chemically modified βcyclodextrins in the liquid and solid state. Eur. J. Pharm. Sci. 3:1995;347-355.
18. Mura P., Faucci M.T., Manderioli A., Bramanti G. Multicomponent systems of econazole with hydroxyacids and cyclodextrins. J. Incl. Phen. 39:2001a;131-138.
19. Mura P., Faucci M.T., Bettinetti G.P. The effect of polyvinylpyrrolidone on hydroxypropyl-βcyclodextrin complexation with naproxen. Eur. J. Pharm. Sci. 13:2001b;187-194.
20. Piel G., Pirotte B., Delneuville I., Neven P., Llabres G., Elargì J., Delatore L. Study of the influence of both cyclodextrins and L-lysine on the aqueous solubility of nimesulide isolation and characterization of nimesulide-L-lysine-cyclodextrin complexes. J. Pharm. Sci. 86:1997;475-480.
21. Redenti E., Szente L., Szejtli J. Drug/cyclodextrin/hydroxy acid multicomponent systems. Properties and pharmaceutical applications. J. Pharm. Sci. 89:2000;1-8.
22. Redenti E., Szente L., Szejtli J. Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications. J. Pharm. Sci. 90:2001;979-986.
23. Steiner, T., Koellner, G., Gessler, K., Saenger, W., 1995. Isostructural replacement of a N-H...O by a C-H...O hydrogen bond in complex stabilisation: crystal structures of β-cyclodextrin complexed with diethanolamine and with pentane-1,5-diol. J. Chem. Soc. Chem. Commun. 511-512.
24. Szejli, J., 1988. Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht.
25. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98:1998;2045-2076.
26. Vikmon, M., Kolbe, I., Szejtli, J., Redenti E., Ventura P., 1999. Preparation and characterization of piroxicam alkali-salt γ-cyclodextrin complexes. Proceedings 9th Intern. Symp. Cyclodextrins, Dordrecht, Kluwer Academic Publishers, pp. 281-284.