Comparative evaluation of ibuprofen/β-cyclodextrin complexes obtained by supercritical carbon dioxide and other conventional methods

Pharmaceutical Research

Volumn 24, Issue 3, 2007, Pages 585-592

  Hussein, Khaled ^a   Türk, Michael ^b   Wahl, Martin A ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

cyclodextrin; Controlled Particle Deposition; Ibuprofen; Poorly water soluble; Supercritical fluids

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; CARBON DIOXIDE; IBUPROFEN;

ANALYTIC METHOD; ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; FREEZE DRYING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; INTERMETHOD COMPARISON; PH; PRIORITY JOURNAL; PROCESS DESIGN; SCANNING ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

BETA-CYCLODEXTRINS; CARBON DIOXIDE; CHROMATOGRAPHY, SUPERCRITICAL FLUID; FREEZE DRYING; IBUPROFEN; KINETICS; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; SOLUBILITY; SPECTROPHOTOMETRY, INFRARED; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE; THERMODYNAMICS; X-RAY DIFFRACTION;

EID: 33847122115     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-006-9177-0     Document Type: Article

References (28)

1. E. Merisko-Liversidge. Nanocrystals: Resolving pharmaceutical formulation issues associated with poorly water-soluble compounds. In Abstract of Papers, Particles Conference, Orlando, Florida, United States, 2002.
2. D. Horter and J. B. Dressman. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv. Drug Deliv. Rev. 46:75-87 (2001).
3. R. D. Connors and E. J. Elder. Using a portfolio of particle growth technologies to enable delivery of drugs with poor water solubility. Drug Delivery Technology 4:78-83 (2004).
4. K.-H. Froemming and J. Szejtli. Cyclodextrins in Pharmacy, Kluwer, Dordrecht, 1994.
5. J. Szejtli. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98:1743-1753 (1998).
6. T. Loftsson and M. E. Brewester. Pharmaceutical application of cyclodextrin. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85:1017-1025 (1996).
7. A. R. Hedeges. Industrial application of cyclodextrin. Chem. Rev. 98:2035-2044 (1998).
8. H. M. C. Marques. Preparation of complexes. Evidence for complex formation. Rev. Port. Farm. 44:157-163 (1994).
9. P. Mura, G. P. Bettinetti, A. Manderioli, M. T. Faucci, G. Bramanti, and A. Sorrenti. Interactions of ketoprofen and ibuprofen with β-cyclodextrins in solution and solid state. Int. J. Pharm. 166:189-203 (1998).
10. I. Bratu, A. Hernanz, J. M. Gavira, and G. H. Bora. FT-IR spectroscopy of inclusion complexes of β-cyclodextrin with fenbufen and ibuprofen. Rom. J. Phys. 50:1063-1069 (2005).
11. F. Veiga, C. Fernandes, and P. Maincent. Influence of the preparation method on the physiochemical properties of tolbutamide/cyclodexrin binary systems. Drug Dev. Ind. Pharm. 27:523-532 (2001).
12. M. Perrut, J. Jung, and F. Leboeuf. Enhancement of dissolution rate of poorly soluble active ingredients by supercritical fluid processes: Part II: Preparation of composite particles. Int. J. Pharm. 288:11-16 (2005).
13. T. Van Hees, G. Piel, B. Evarad, X. Otte, L. Thunus, and L. Delattre. Application of supercritical carbon dioxide for the preparation of a piroxicam-β-cyclodextrin inclusion compound. Pharm. Res. 16:1864-1870 (1999).
14. M. Charoenchaitrakool, F. Daghani, and N. R. Foster. Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-beta-cyclodextrin. Int. J. Pharm. 239:103-112 (2002).
15. N. Bandi, W. Wei, C. B. Roberts, L. P. Korta, and U. B. Kompella. Preparation of budesonide- and indomethacin-hydroxypropyl-β-cyclodextrin (HPβCD) complexes using a single-step, organic-solvent-free supercritical fluid process. Eur. J. Pharm. Sci. 23:159-168 (2004).
16. 2, J. Supercrit. Fluids (2006; article in press, available online March 20, 2006).
17. M. Tuerk, P. Hils, K. Hussein, and M. A. Wahl. Manufacture of submicron-substance-loaded drug carriers with supercritical fluids. Chem. Ing. Tech. 76:1379 (2004).
18. 2 and other conventional methods. In Abstract of Papers, 10th European Meeting on Supercritical Fluids, Colmar, France, 2005. ISBN 2-905267-47-X.
19. A. Diefenbacher and M. Tuerk. Phase equilibria of organic solid solutes and supercritical fluids with respect to the RESS process. J. Supercrit. Fluids 22:175-184 (2002).
20. M. Kurozumi, N. Nambu, and T. Nagai. Inclusion compounds of non-steroidal antiinflammatory and other slightly soluble drugs with α- and β-cyclodextrin in powdered form. Chem. Pharm. Bull. 23:3062-30068 (1975).
21. Y. Nozawa, K. Susuki, Y. Sadzuka, A. Miyagishima, and S. Hirota. Effects of shear rate in roll mixing on mechanical complex formation of ibuprofen with β-cyclodextrin. Pharm. Acta Helv. 69:135-139 (1994).
22. K. J. Waleczek, H. M. Cabral Marques, B. Hempel, and P. C. Schmidt. Phase solubility studies of pure (-)-a-bisabolol and camomile essential oil with β-cyclodextrin. Eur. J. Pharm. Biopharm. 55:247-251 (2003).
23. C. Kaiser, Herstellung. In-Line-Einschluss und Charakterisierung Lipophiler und Hydrophiler Kamillenextrakte unter Einsatz von verdichtetem Kohlendioxid. Ph.D. thesis, Pharmaceutical Technology, Tübingen (Germany), 2003.
24. H. Stricker. Die in-vitro-Untersuchung der Verfügbarkeit von Arzneistoffen im Gastrointestinaltrakt. Pharm. Ind. 31:794-799 (1969).
25. J. Heinrich, M. Chalabala, and J. Rak. Drug dissolution and weibull function. Acta Pharm. Technol. 32:94-96 (1986).
26. M. N. Reddy, T. Rehana, S. Ramakrishna, K. P. R. Chowdary, and P. V. Diwan. β-Cyclodextrin complexes of celecoxib: Molecular-modeling, characterization, and dissolution studies. AAPS PharmSci 6(1): (2004).
27. R. Govindarajan and M. S. Nagrsenker. Influence of preparation methodology on solid-state properties of an acidic drug-cyclo-dextrin system. J. Pharm. Pharmacol. 56:725-733 (2004).
28. S. Charumanee. Amorphization and dissolution studies of Acetaminophen-β-Cyclodextrin inclusion complexes. CMU J. 13(1):13-23 (2004).