Solid-state β-cyclodextrin complexes containing indomethacin, ammonia and water. I. Formation studies

International Journal of Pharmaceutics

Volumn 165, Issue 1, 1998, Pages 1-14

  Casella, R ^a   Williams, D A ^b   Jambhekar, S S ^b  

^a ASTRAZENECA   (United Kingdom)

^b MASSACHUSETTS COLLEGE OF PHARMACY AND HEALTH SCIENCES   (United States)

Author keywords

cyclodextrin; Complex formation; Differential scanning calorimetry; Indomethacin; Infrared; Nuclear magnetic resonance; Thermogravimetric analysis; Ultraviolet; X ray diffraction

Indexed keywords

AMMONIA; BETA CYCLODEXTRIN; INDOMETACIN; WATER;

ARTICLE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DETERMINATION; HYDROPHILICITY; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLID STATE; THERMOGRAVIMETRY; WATER CONTENT; X RAY DIFFRACTION;

EID: 0032550343     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(97)00330-X     Document Type: Article

References (31)

1. Borka L. The polymorphism of indomethacine. Acta. Pharm. Suec. 11:1974;295-303.
2. Bergeron R.J., Channing M.A., Gibeily G.J., Pillor D.M. Disposition requirements for binding in aqueous solution of polar substrates in cyclohexaamylose cavity. J. Am. Chem. Soc. 99(15):1977;5146-5151.
3. Bergeron R.J., Channing M.A., McGovern K.A. Dependence of cycloamylose-substrate binding on charge. J. Am. Chem. Soc. 100(9):1978;2878-2883.
4. Bergeron, R.J., 1984. Cycloamylose-substrate binding. In: Atwood, J.L. et al. (Eds.), Inclusion Compounds III. Academic Press, New York, pp. 417-422.
5. Celebi N., Nagai T. Improvement of dissolution characteristics of piromidic acid by dimethyl-β-cyclodextrin complexation. Drug Dev. Ind. Pharm. 14(1):1988;63-75.
6. Duchene, D., Glomot, F., Vaution, C., 1987. Pharmaceutical applications of cyclodextrins. In: Duchene, D. (Ed.), Cyclodextrins and their Industrial Uses. Editions de Sante, Paris, France, p. 225.
7. Frank, S.G., 1975. Inclusion compounds. J. Pharm. Sci. 64 (10).
8. Fromming, K.H., Mehnert, W., Bady, P., Kraus, C., Stein, M., Wedelich V., 1990. Competitive reactions of cyclodextrin inclusion compounds. Min. Int. 5th Symp. Cyclodextrins, pp. 392-398.
9. Hamada Y., Nambu N., Nagai T. Interactions of α- and β-cyclodextrin with several non-steroidal anti-inflammatory drugs in aqueous solution. Chem. Pharm. Bull. 23(6):1975;1205-1211.
10. Imaizumi H., Nambu N., Nagai T. Stability and several physical properties of amorphous and crystalline forms of indomethacin. Chem. Pharm. Bull. 28(9):1980;2565-2569.
11. Jenkins, G.L., Christian, J.E., Hagar, G.P., Quantitative Pharmaceutical Chemistry, 5th ed., The Blakiston Division, McGraw-Hill, New York, 1957, pp. 451-456.
12. Kurozumi M., Nambu N., Nagai T. Inclusion compounds of non-steroidal anti-inflammatory and other slightly water soluble drugs with α- and β-cyclodextrins in powdered form. Chem. Pharm. Bull. 23(12):1975;3062-3068.
13. Le Bas, G., Rysanek N., 1987. Structural aspects of cyclodextrins. In: Duchene, D. (Ed.), Cyclodextrins and their Industrial Uses. Editions de Sante, Paris, France, pp. 103-130.
14. Lin, S.Z., Wouessidjewe, D., Poelman, M.C., Duchene, D., 1992. Preparation of indomethacin/cyclodextrin complexes for dermal application. Min. Int. 6th Symp. Cyclodextrins, pp. 522-528.
15. Lin S.Z., Wouessidjewe D., Poelman M.C., Duchene D. Indomethacin and cyclodextrin complexes. Int. J. Pharm. 69:1991;211-219.
16. Liu F., Kildsig D.O., Mitra A.K. Cyclodextrin/weak-electrolyte complexation: interpretation and estimation of association constants from phase solubility diagrams. Pharm. Res. 9(12):1992;1671-1672.
17. Miyahara M., Takahashi T. Determination of stability constants of complexes by the nonlinear optimization method and analysis of solubility curves. Chem. Pharm. Bull. 30(1):1982;288-295.
18. Myles, A.M.C., Lee, P.K.Y., France, G., Barlow, D.J., Lawrence, M.J., 1990. Structural Studies of indomethacin/cyclodextrin complexes. Min. Int. 5th Symp. Cyclodextrins, pp. 173-179.
19. Nakai Y., Yamamoto K., Terada K., Kajiyama A. Relationships between crystallinity of β-cyclodextrin and tablet characteristics. Chem. Pharm. Bull. 33(11):1985;5110-5112.
20. Nambu N., Shimoda M., Takahashi Y., Ueda H., Nagai T. Bioavailability of powered inclusion compounds of non-steroidal anti-inflammatory drugs with β-cyclodextrin in rabbits and dogs. Chem. Pharm. Bull. 26(10):1978;2952-2956.
21. Rosanske T.W., Connors K.A. Stoichiometric model of α-cyclodextrin complex formation. J. Pharm. Sci. 69(5):1980;564-567.
22. Saenger W. Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. Engl. 19:1980;344-362.
23. Seo H., Tsuruoka M., Hashimoto T., Fujinaga T., Otagiri M., Uekama K. Enhancement of oral bioavailability of spironolactone by β- and γ-cyclodextrin complexations. Chem. Pharm. Bull. 31(1):1983;286-291.
24. Szejtli, J., 1982. Cyclodextrins and their Inclusion Complexes. Akademiai Kiado, Budapest, pp. 40-41, 101-109, 213-214, 236-243.
25. Szejtli J., Szente L. Interaction between indomethacin and β-cyclodextrin. Pharmazie. 36:1981;694-698.
26. Szente L., Apostol I., Gerloczy A., Szejtli J. Suppositories containing cyclodextrin complexes. Part 2: dissolution and absorption studies. Pharmazie. 40(H6):1985;406-407.
27. Tabushi I., Kiyosuke Y., Sugimoto T., Yamamura K. Approach to the aspects of driving force of inclusion by β-cyclodextrin. J. Am. Chem. Soc. 100(3):1978;916-919.
28. 1 methyl ester by cyclodextrin complexation. J. Pharm. Sci. 68(8):1979;1059-1060.
29. Uekama K., Narisawa S., Hirayama F., Otagiri M. Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation. Int. J. Pharm. 16:1983;327-338.
30. Wong A.B., Lin S., Connors K.A. Stability constants for complex formation between α-cyclodextrin and some amines. J. Pharm. Sci. 72(4):1983;388-390.
31. Wouessidjewe, D., Lin, S.Z., Djedaini, F., Perly, B., Duchene D., 1990. Investigation of indomethacin/β-cyclodextrin and indomethacin/hydroxypropyl β-cyclodextrin inclusion complexes, NMR contribution to prove the inclusion. Min. Int. 5th Symp. Cyclodextrins, pp. 332-338.