Prednisone/cyclodextrin inclusion complexation: Phase solubility, thermodynamic, physicochemical and computational analysis

Journal of Solution Chemistry

Volumn 38, Issue 1, 2009, Pages 83-94

  Ghuzlaan, Ameer ^a   Al Omari, Mahmoud M ^b   Al Sou'od, Khaldoun A ^a  

^a AL AL BAYT UNIVERSITY   (Jordan)

^b JORDANIAN PHARMACEUTICAL MANUFACTURING COMPANY   (Jordan)

Author keywords

Cyclodextrin; Inclusion complexation; Molecular modeling; Phase solubility; Prednisone; Thermodynamics

Indexed keywords

EID: 57249113723     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-008-9349-0     Document Type: Article

References (36)

1. Szejtli, J.: Cyclodextrin Technology, pp. 8-72. Kluwer, Dordrecht (1989)
2. N. Sadlej-Sosnowska 1997 Influence of the structure of steroid hormones on their association with cyclodextrin: A high-performance liquid chromatography study J. Inclusion Phenom. Molec. Recog. Chem. 27 31 40
3. T. Cserháti E. Forgács 1998 Inclusion complex formation of steroidal drugs with hydroxypropyl-β-cyclodextrin studied by charge-transfer chromatography J. Pharm. Biomed. Anal. 18 179 185
4. K.G. Flood E.R. Reynolds N.H. Snow 2000 Characterization of inclusion complexes of betamethasone-related steroids with cyclodextrin using high-performance liquid chromatography J. Chrom. A 903 49 65
5. K.G. Flood E.R. Reynolds N.H. Snow 2001 Determination of apparent association constants of steroid-cyclodextrin inclusion complexes using a modification of the Hummel-Dreyer method J. Chrom. A 913 261 268
6. P. Forgo G. Göndös 2002 A study of β-cyclodextrin inclusion complexes with progesterone and hydrocortisone using rotating frame overhauser spectroscopy Monatshefte für Chemie 133 101 106
7. P. Weinzinger P. Weiss-Greiler W. Snor H. Viernstein P. Wolschann 2007 Molecular dynamics simulations and quantum chemical calculations on β-cyclodextrin-spironolactone complex J. Inclusion Phenom. Macrocycl. Chem. 57 29 33
8. I.K. Chun D.S. Yun 1993 Inclusion complexation of hydrocortisone butyrate with cyclodextrins and dimethyl-β-cyclodextrin in aqueous solution and in solid state Int. J. Pharm. 31 91 103
9. R.F.L. Vianna M.V.L.B. Bentley G. Ribeiro F.S. Carvalho A.F. Neto D.C.R. de Oliveira J.H. Collett 1998 Formation of cyclodextrin inclusion complexes with corticosteroids: their characterization and stability Int. J. Pharm. 167 205 213
10. S.H. de Hassonville B. Perly G. Piel T.V. Hees V. Barillaro P. Bertholet L. Delattre B. Evrard 2002 Inclusion complexes of cyproterone acetate with cyclodextrin in aqueous solution J. Incl. Phenom. Macrocycl. Chem. 44 289 292
11. I. Lula M.F. Gomes D. Piló-Veloso A.L.O. de Noronha H.A. Duarte R.A.S. Santos R.D. Sinisterra 2006 Spironolactone and its complexes with β-cyclodextrin: Modern NMR characterization and structural DFTB-SCC calculations J. Incl. Phenom. Macrocycl. Chem. 56 293 302
12. K.A. Al-Sou'od 2008 Investigation of the hydrocortisone-β- cyclodextrin complex by phase solubility method: Theoretical and practical considerations J. Solution Chem. 37 119 133
13. F.M. Anderson H. Bundgaard 1984 The influence of cyclodextrin complexation on the stability of betamethasone-17-valerate Int. J. Pharm. 20 155 162
14. K. Arimori A. Sakai M. Otagiri K. Uekama 1984 Improvement in biopharmaceutics of prednisolone by β- and γ-cyclodextrins J. Incl. Phenom. Macrocycl. Chem. 1 387 394
15. M.H. Elshaboury 1990 Physical properties and dissolution profiles of tablets directly compressed with β-cyclodextrin Int. J. Pharm. 63 95 100
16. V.J. Stella H.K. Lee D.O. Thompson 1995 The effect of SBE4-β-CD on i.m. prednisolone pharmacokinetics and tissue damage in rabbits: Comparison to a co-solvent solution and a water-soluble prodrug Int. J. Pharm. 120 197 204
17. 7m-β-CD Pharm. Res. 15 1562 1568
18. J. Filipović-Grčić D. Voinovich M. Moneghini M. Bećirević-Laćan L. Magarotto I. Jalšenjak 2000 Chitosan microsphere with hydrocortisone and hydrocortisone-hydroxypropy-β- cyclodextrin inclusion complex Eur. J. Pharm. Sci. 9 373 379
19. G. Zoppetti N. Puppini M. Pizzutti A. Fini T. Giovani S. Comini 2007 Water soluble progesterone-hydroxypropyl-β-cyclodextrin complex for injectable formulations J. Incl. Phenom. Macrocycl. Chem. 57 283 288
20. AHFS drug information. Prednisone. www.ashp.org/mngrphs/ahfs/a382796.htm
21. Prednisone USP monograph. In United States Pharmacopoeia (USP); 31th edn. pp. 3068-3069, USP Convention. INC: Maryland (2008)
22. J.J. Ferry A.M. Horvath I. Bekersky E.C. Heath C.F. Ryan W.A. Colburn 1988 Relative and absolute bioavailability of prednisone and prednisolone after separate oral intravenous doses J. Clin. Pharmacol. 28 81 87
23. T. Higuchi K.A. Connors 1965 Phase solubility techniques Adv. Anal. Chem. Instr. 4 117 212
24. 2 type phase solubility diagrams, complex formation and chemical speciation of soluble species J. Incl. Phenom. Macrocycl. Chem. 31 243 264
25. K.A. Al-Sou'od M.B. Zughul A.A. Badwan 2006 Experimental and molecular mechanical studies of complexation of some 2H- and 3H-indole derivative with aqueous β-cyclodextrin J. Solution Chem. 35 1377 1388
26. K.A. Al-Sou'od 2007 Investigation of the hydrocortisone-β- cyclodextrin complex by phase solubility method: Some theoretical and practical considerations J. Solution Chem. 37 119 133
27. K. Linder W. Saenger 1982 Crystal and molecular structure of cyclohepta-amylose dodecahydrate Carbohydr. Res. 99 103 115
28. W. Saenger J. Jacob K. Gessler T. Steiner D. Hoffman H. Sanbe K. Koizumi S.M. Smith T. Takaha 1998 Structures of the common cyclodextrins and their large analogues-beyond the doughnut Chem. Rev. 98 1787 1802
29. K. Harata 1987 The structure of the cyclodextrin complex. XX. Crystal-structure of uncomplexed hydrate γ-cyclodextrin Bull. Chem. Jpn. 60 2763 2767
30. J. Taraszewska K. Migut M. Kozbiat 2003 Complexation of flutamide by native and modified cyclodextrins J. Phys. Org. Chem. 16 121 126
31. Nalluri, B.N., Chowdary, K.R., Murthy, K.R., Hayman, A.R., Becket, G.: Physicochemical characterization and dissolution properties of nimesulide-cyclodextrin binary systems. AAPS PharmSciTech. 4 Article 2 (2003). http://www.aapspharmscitech.org
32. A. Yoshida M. Yamamoto T. Irie F. Hirayama K. Uekama 1989 Some pharmaceutical properties of 3-hydroxypropyl- and 2,3-dihydroxypropyl-beta- cyclodextrins and their solubilizing and stabilizing abilities Chem. Pharm. Bull. 37 1059 1063
33. L. Ribeiro F. Veiga 2002 Complexation of vinpocetine with cyclodextrins in the presence or absence of polymers: Binary and ternary complexes preparation and characterization J. Incl. Phenom. Macrocycl. Chem. 44 251 256
34. L.L. Yannis 1995 Complexation of haloperidol with a water-soluble β-cyclodextrin polymer: Characterization of the inclusion complex in solid state and in aqueous solution Pharm. Sci. 1 509 512
35. L.L. Yannis V. Varka G. Gregoriadis 1997 Novel non-acidic formulations of haloperidol complexed with β-cyclodextrin derivatives J. Pharm. Biomed. Anal. 16 263 268
36. C. Wensheng Y. Xuexia S. Xueguang P. Zhongxiao 2005 Bimodal complexation of steroids with cyclodextrin by a flexible docking algorithm J. Incl. Phenom. Macrocycl. Chem. 51 41 51