Maturation of a ketoprofen/β-cyclodextrin mixture with supercritical carbon dioxide

Journal of Supercritical Fluids

Volumn 41, Issue 3, 2007, Pages 429-439

  Bounaceur, Arezki ^a   Rodier, Elisabeth ^a   Fages, Jacques ^a  

^a ECOLE DES MINES D ALBI CARMAUX   (France)

Author keywords

Association complex; Beta cyclodextrin; Ketoprofen; Supercritical carbon dioxide; Supercritical maturation process

Indexed keywords

ASSOCIATION REACTIONS; CARBON DIOXIDE; COMPLEXATION; INCLUSIONS; ORGANIC SOLVENTS; STOICHIOMETRY;

ASSOCIATION COMPLEX; BETA CYCLODEXTRIN (CD); KETOPROFEN (KP); SUPERCRITICAL CARBON DIOXIDE; SUPERCRITICAL MATURATION PROCESS;

SUPERCRITICAL FLUIDS;

EID: 34247497632     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2006.11.004     Document Type: Article

References (35)

1. Van Hees T., Piel G., Evrard B., Otte X., Thunus L., and Delattre L. Application of supercritical carbon dioxide for the preparation of a piroxicam β-cyclodextrin inclusion compound. Pharm. Res. 16 (1999) 1864-1870
2. Van Hees T., Piel G., Henry de Hassoville S., Evrard B., and Delattre L. Determination of the free/included piroxicam ratio in cyclodextrin complexes: comparison between UV spectrophotometry and differential scanning calorimetry. Eur. J. Pharm. Sci. 15 (2002) 347-353
3. Charoenchaitrakool M., Dehghani F., and Foster N.R. Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-/β-cyclodextrin. Int. J. Pharm. 239 (2002) 103-112
4. B. Castel, Mise en forme des solides, Techniques de l'Ingénieur, Aspect théoriques [J 3 380], Génie des procédés, 1995.
5. Vavia P.R., and Tayade P.T. Inclusion complexation of ketoprofen with β-cyclodextrins. Indian J. Pharma. Sci. 61 2 (1999) 97-99
6. Fages J., Lochard H., Rodier E., Letourneau J.-J., and Sauceau M. La génération des solides divisés par fluides supercritiques. Can. J. Chem. Eng. 81 (2003) 161-175
7. Debenedetti P.G., Tom J.W., Kwauk X., and Yeo S.D. Rapid expansion of supercritical solutions (RESS): fundamentals and applications. Fluid Phase Equilib. 82 (1993) 303-310
8. Reverchon E. Review: supercritical antisolvent precipitation of micro- and nano-particles. J. Supercrit. Fluids 15 (1999) 1
9. Weidner E., Knez Z., and Novak Z. PGSS (particles from gas saturated solutions)-a new process for powder generation. Proceedings of the Third International Symposium on Supercritical Fluids. Strasbourg (1994) 229
10. Bahrami M., and Ranjbarian S. Production of micro- and nano-composite particles by supercritical carbon dioxide. J. Supercrit. Fluids 40 (2007) 263-283
11. Foster N.R., Mammucari R., and Dehghari F. Coprecipitation of pharmaceuticals using gas antisolvent technique. Proceeding of the Eighth Meeting on Supercritical Fluids. Bordeaux, France, Tome I (2002) 321-326
12. Barillaro V., Piel G., Bertholet S., Henry de Hassonville S., Evrard B., and Delattre L. Inclusion of miconazole into cyclodextrins by means of supercritical carbon dioxide: influence of the addition of an acidic ternary compound. Proceedings of the Sixth International Symposium on Supercritical Fluids. Versailles (2003) 1897
13. 1H NMR spectroscopy: preliminary results. Proceedings of the Sixth International Symposium on Supercritical Fluids. Versailles (2003) 1903
14. Lochard H., Rodier E., Sauceau M., Letourneau J.-J., Freiss B., Joussot-Dubien C., and Fages J. A three step supercritical process to improve the dissolution rate of eflucimibe. Proceedings of the Sixth International Symposium on Supercritical Fluids. Versailles (2003) 1659
15. Duchêne D., Debruères B., and Brétillon A. Les cyclodextrines, nature origine et intérêt en pharmacie galénique. Labo-Pharma Prolab. Tech. 32 (1984) 842-849
16. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1754
17. Arima H., Adachi H., Irie T., Uekama K., and Pitha J. Enhancement of the anti-inflammatory effect of ethyl 4-biphenyllacetate in ointment by β-cyclodextrin derivatives: increased absorption and localized activations of the prodrug in rats. Pharm. Res. 7 (1990) 1152-1156
18. Amdidouche D., Montassier P., Poelman M.-C., and Duchêne D. Evaluation by laser Doppler velocimetry of the attenuation of tretinoin induced skin irritation by β-cyclodextrin complexation. Int. J. Pharm. 111 (1994) 111-116
19. Lin S.-Z., Woessidjewe D., Poelman M.-C., and Duchêne D. In vivo evaluation of indomethacin/cyclodextrin complexes, gastrointestinal tolerance and dermal anti-inflammatory activity. Int. J. Pharm. 106 (1994) 63-67
20. Macnaughton S.J., Kikic I., Foster N.R., Alessi P., Cortisi A., and Colombo I. Solubility of anti-inflammatory drugs in supercritical carbon dioxide. J. Chem. Eng. Data 41 (1996) 1083-1086
21. Mura P., Bettinetti G.P., Manderioli A., Faucci M.T., Bramanti G., and Sorrenti M. Interaction of ketoprofen and ibuprofen with β-cyclodextrins in solution and in the solid state. Int. J. Pharm. 166 (1998) 189-203
22. A. Gil, Recherche de complexation entre une nouvelle entité chimique et des cyclodextrines par co-broyage et malaxage, Thèse de doctorat de l'université de Paris VI, 2001.
23. Fromming K.-H., and Szejtli J. In: Davies J.E.D. (Ed). Cyclodextrins in Pharmacy (1994), Kluwer Academic Publishers, Dordrecht 224
24. E. Stahl, K.W. Quirin, D. Gerard, Dense gases for extraction and refining (M.R.F. Ashworth, Trans.), Springer and Verlag, New York, 1988.
25. Peng D.-Y., and Robinson D. A new two constant equation of state. Ind. Eng. Chem. Fundam. 15 (1976) 59-64
26. Mura P., Manderioli A., Bramanti G., Furlanetto S., and Pinzauti S. Utilization of differencial scanning calorimetry as a screening technique to determine the compatibility of ketoprofen with excipients. Int. J. Pham. 119 (1995) 71-79
27. Giordano F., Novak C., and Moyano J.R. Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim. Acta 380 (2001) 123-151
28. Mura P., Fauci M.T., Parrini P.L., Furlanetto S., and Pinzauti S. Influence of the preparation method on the physicochemical properties of ketoprofen-cyclodextrin binary systems. Int. J. Pharm. 179 (1999) 117-128
29. Rodier E., Lochard H., Sauceau M., Letourneau J.-J., Freiss B., and Fages J. A three step supercritical process to improve the dissolution rate of eflucimibe. Eur. J. Pharm. Sci. 26 (2005) 184-193
30. Marini A., Berbenni V., Bruni G., and Mustarelli P. Thermoanalytical and spectroscopic characterization of βcyclodextrin/ketoprofen inclusion complexes. J. Inclus. Phen. Mol. Rec. Chem. 22 (1995) 221-234
31. Bruni G., Marini A., Berbenni V., Riccardi R., and Villa M. A novel method to obtain a β-cyclodextrin inclusion compound by solid state reaction: the ketoprofen case revisited. J. Inclusion Phenom. Macrocycl. Chem. 35 (1999) 517-530
32. Bilal M., de Brauer M., Claudy P., Germain P., and Létoffé J.M. β-Cyclodextrin hydration: a calorimetric and gravimetric study. Thermochem. Acta 249 (1995) 63-73
33. Hoenigman S.M., and Evans C.E. Spectroscopic determination of pressure induced shifts in inclusion complexation equilibria. Anal. Chem. 69 (1997) 2136-2142
34. Sueshi Y., Nishimura N., Hirata K., and Kuwata K. An ESR study of pressure effect on the inclusion complex formation of cyclodextrins with di-tert-butyl nitroxide. J. Phys. Chem. 95 (1991) 5359-5361
35. Mullin J.W. Crystallization. third rev. ed. (1992), Butterworth-Heinemann, Oxford