Physicochemical characterization of drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 57, Issue 1-4, 2007, Pages 223-231

  Al Marzouqi, Ali ^a   Jobe, Baboucarr ^a   Corti, Giovanna ^b   Cirri, Marzia ^b   Mura, Paola ^b  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Benzocaine; Bupivacaine; Cyclodextrin; Inclusion complex; Mepivacaine; Supercritical carbon dioxide mepivacaine

Indexed keywords

EID: 34047130130     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-006-9192-0     Document Type: Conference Paper

References (36)

1. Covino, B., Vassallo, H.: Local Anesthetics. Grune and Stratton, New York (1976)
2. Benumof, J.: Clinical Procedures in Anesthesia and Intensive Care. JB Lippincott, Philadelphia (1992)
3. Szejtli, J.: Cyclodextrins in Pharmacy, Dordrecht. Kluwer, The Netherlands (1994)
4. Duchene, D., Wouessidjewe, D.: Pharmaceutical uses of cyclodextrins and derivatives. Drug Dev. Ind. Pharm. 16, 2487-2499 (1990)
5. Lee, B., Lee, J.: Enhancement of solubility and dissolution rate of poorly water-soluble naproxen by complexation with 2-hydroxypropyl-β- cyclodextrin. Arch. Pharm. Res. 18, 22-26 (1995)
6. Dhanaraju, M., Kumaran, K., Baskaran, T., Moorthy, M.: Enhancement of bioavailability of griseofulvin by its complexation with beta-cyclodextrin. Drug Dev. Ind. Pharm. 24(6), 583-587 (1998)
7. Dollo, G., Thompson, D., Le Corre, P., Chevanne, F., Le Verge, R.: Inclusion complexation of amide-typed local anesthetics with β-cyclodextrin and its derivatives. III. Biopharmaceutics of bupivacaine-SBE7-βCD complex following percutaneous sciatic nerve administration in rabbits. Int. J. Pharm. 164(1-2), 11-19 (1998)
8. Greczy, J., Bruhwyler, J., Scuvee-Moreau, J., Seutin, V., Masset, H., Van Heugen J., Dresse, A., Lejeune, C., Decamp, E., Szente, L., Szejtli, J., Liegeois, J.: The inclusion of fluoxetine into gamma-cyclodextrin increases its bioavailability: behavioural, electrophysiological and pharmacokinetic studies. Psychopharmacology 151(4), 328-334 (2000)
9. Nagarsenker, M., Meshram, R., Ramprakash, G.: Solid dispersion of hydroxypropyl beta-cyclodextrin and ketorolac: Enhancement of in-vitro dissolution rates, improvement in anti-inflammatory activity and reduction in ulcerogenicity in rats. J. Pharm. Pharmacol. 52, 949-956 (2000)
10. Kang, J., Kumar, V., Yang, D., Chowdhury, P., Hohl, R.: Cyclodextrin complexation: influence on solubility, stability and cytotoxicity of camptothecin, an antineoplastic agent. Eur. J. Pharm. Sci. 15, 163-170 (2002)
11. Stanley, T.: New routes of administration and new delivery systems of anesthetics. Anaesthesiolog 38, 665-668 (1988)
12. Szejtli, J.: Cyclodextrins and their Inclusion Complexes. Akademiai Kiado, Budapest (1982)
13. Jones, S. Grant, D., Hadgraft, J., Parr, G.: Cyclodextrins in the pharmaceutical sciences. Part I: Preparation, structure and properties of cyclodextrins and cyclodextrin inclusion compounds. Acta Pharm. Technol. 30, 213-223 (1984)
14. Irie, T., Uekama K.: Protection against the photosensitized skin irritancy of chlorpromazine by cyclodextrin complexation. J. Pharmacobiol. Dyn. 8(9), 788-791 (1985)
15. Mura, P., Faucci, M., Bettinetti, G.: The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-β- cyclodextrin. Eur. J. Pharm. Sci. 13, 187-194 (2001)
16. Cirri, M., Rangoni, C., Maestrelli, F., Corti, G., Mura, P.: Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes. Drug Dev. Ind. Pharm. 31(7), 697-707 (2005)
17. Mura, P., Furlanetto, S., Cirri, M., Maestrelli, F., Corti, G., pinzauti, S.: Interaction of naproxen with ionic cyclodextrins in aqueous solution and in the solid state. J. Pharm. Biomed. Anal. 37, 987-994 (2005)
18. Veiga, M., Merino, M., Cirri, M., Maestrelli, F., Mura, P.: Comparative study on triclosan interactions in solution and in the solid state with natural and chemically modified cyclodextrins. J. Incl. Phenom. 53(1), 77-83 (2005)
19. Hirayama, F., Uekama, K.: Cyclodextrins and their Industrial Uses. Editions de Santé, Paris (1987) pp. 133
20. Blanco, J., Vila-Jato, J.L., Otero, F., Anguiano, S.: Influence of the method of preparation on inclusion complexes of naproxen with different cyclodextrins. Drug Dev. Ind. Pharm. 17, 943-957 (1991)
21. Mura, P., Adragna E., Rabasco, A., Moyano, J., Perez-Martinez, J., Arias, M., Gines, J.: Effects of the host cavity size and the preparation method on the physicochemical properties of ibuproxam-cyclodextrin systems. Drug Dev. Ind. Pharm. 25, 279-287 (1999a)
22. Mura, P., Faucci M.T., Manderioli A., Bramanti G.: Influence of the preparation method on the physicochemical properties of binary systems of econazole with cyclodextrins. Int. J. Pharm. 193, 85-95 (1999b)
23. Mura, P., Faucci, M.T., Parrini, P.L., Furlanetto, S., Pinzauti, S.: Influence of the preparation method on the physicochemical properties of ketoprofen-cyclodextrin binary systems. Int. J. Pharm. 179, 117-128 (1999c)
24. Kiran, E., Brennecke J.: Supercritical Fluid Engineering Science, ACS Symposium Series 514, American Chemical Society, Washington DC (1993)
25. Van Hees, T., Piel, G., Evrard, B., Otte, X., Thunus, L., Delattre, L.: Application of supercritical carbon dioxide for the preparation of a piroxicam-β-cyclodextrin inclusion compound. Pharm. Res. 16, 1864-1870 (1999)
26. Junco, S. Casimiro T., Ribeiro, N., da Ponte, M.N., Cabral Marques, H.: A comparative study of naproxen-beta cyclodextrin complexes prepared by conventional methods and using supercritical carbon dioxide. J. Incl. Phenom. 44(1-4), 117-121 (2002)
27. Charoenchaitrakool, M., Dehghani, F., Foster, R.F.: Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-β-cyclodextrin. Int. J. Pharm. 239(1-2), 103-112 (2002)
28. 1H NMR characterization. Carbohydr. Res. 338(21), 2227-2232 (2003)
29. Al-Marzouqi A., Shehatta, I., Jobe, B., Dowaidar, A.: Phase solubility and inclusion complex of itraconazole with β-cyclodextrin using supercritical carbon dioxide. J. Pharm. Sci. 95, 292-304 (2006)
30. Shehatta, I., Al-Marzouqi, A., Jobe, B., Dowaidar, A.: Enhancement of aqueous solubility of itraconazole by complexation with cyclodextrins using supercritical carbon dioxide. Can. J. Chem. 83(10), 1833-1838 (2005)
31. de Jong, R.H.: Local Anestethics. Springfield, Illinois (1994)
32. Strichartz, G.R., Sanchez, V., Arthue, R., Chafetz, R., Martin, D.: Fundamental properties of local anesthetics. II. Measured octanol:buffer partition coefficients and pK(a) values of clinically used drugs. Anest. Analg. 71(2), 158-170 (1990)
33. Dollo, G., LeCorre, P., Chevanne, Le Verge, R.: Inclusion complexation of amide-typed local anaesthetics with β-cyclodextrin and its derivatives. I. Physicochemical characterization. Int. J. Pharm. 131(2), 219-228 (1996)
34. Pinto, L., Fraceto L., Santana, M., Pertinhez, T., Oyama Junior, S., de Paula, E.: Physico-chemical characterization of benzocaine-β-cyclodextrin inclusion complexes. J. Pharmaceut. Biomed. 39(5), 956-963 (2005)
35. Hassan, A., Tang, Y., Ayres, J.: Itraconazole formation using supercritical carbon dioxide. Drug Dev. Ind. Pharm. 30(10), 1029-1035 (2004)
36. Khan, K.A.: The concept of dissolution efficiency. J. Pharm. Pharmacol. 27(1), 48-49 (1975)