Drug/cyclodextrin/hydroxy acid multicomponent systems. Properties and pharmaceutical applications

Journal of Pharmaceutical Sciences

Volumn 89, Issue 1, 2000, Pages 1-8

  Redenti, Enrico ^a   Szente, Lajos ^b   Szejtli, József ^b  

^a CHIESI FARMACEUTICI S P A   (Italy)

^b CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ALBENDAZOLE; ASCORBIC ACID; ASTEMIZOLE; CINNARIZINE; CITRIC ACID; CLOMIFENE; CYCLOBENZAPRINE; CYCLODEXTRIN; DOMPERIDONE; DRUG; GLUCONIC ACID; HYDROXYACID; KETOCONAZOLE; LACTIC ACID; MALIC ACID; MICONAZOLE; OMEPRAZOLE; TAMOXIFEN; TARTARIC ACID; TERFENADINE;

AREA UNDER THE CURVE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG FORMULATION; DRUG SOLUBILITY; SHORT SURVEY;

ANIMALS; CYCLODEXTRINS; DRUG SYNERGISM; EXCIPIENTS; HUMANS; HYDROXY ACIDS; PHARMACEUTIC AIDS; SOLUBILITY;

EID: 0033951798     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-6017(200001)89:1<1::AID-JPS1>3.0.CO;2-W     Document Type: Article

References (75)

1. Saenger W. 1980. Cyclodextrin inclusion compounds in research and industry. Chem Int Ed Engl 19:344-362.
2. Szejtli J. 1982. Cyclodextrins and their inclusion complexes. Budapest: Akadémiai Kiadó.
3. Duchêne D. 1987. Cyclodextrins and their industrial uses. Paris: Editions de Santé.
4. Szejtli J. 1988. Cyclodextrin technology. Dordrecht: Kluwer Academic Publishers.
5. Duchêne D. 1991. New trends in cyclodextrin and derivatives. Paris: Editions de Santé.
6. Frömming KH, Szejtli J. Cyclodextrins in pharmacy. Dordrecht: Kluwer Academic Publishers.
7. Uekama K, Hirayama F, Irie T. 1994. Application of cyclodextrins. Drug Target Deliv 3:411-456.
8. Loftsson T, Brewster M. 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilisation and stabilization. J Pharm Sci 85:1017-1025.
9. Loftsson T, Brewster M. 1997. Cyclodextrins as pharmaceutical excipients. Pharm Tech Eur May: 26-34.
10. Stella V, Rajewski R. 1997. Cyclodextrin: Their future in drug formulation and delivery. Pharm Res 14-556-567.
11. Miyazawa I, Ueda H, Nagase H, Endo T, Kobayashi S, Nagai T. 1995. Physicochemical properties and inclusion complex formation of δ-cyclodextrin. Eur J Pharm Sci 3:153-162.
12. Coleman A, Nicolis I, Keller N, Dalbiez JP. 1992. Aggregation of cyclodextrins: An explanation of the abnormal solubility of β-cyclodextrin. J Incl Phenom 13:139-143.
13. Bellanger N, Perly B. 1994. Investigation of the dynamics of cyclodextrins and their inclusion complexes in water by deuterium NMR. Magn Reson Chem 32:8-11.
14. Higuchi T, Connors KA. 1965. In: Reilly CN, editor. Advances in analytical chemistry and instrumentation, Vol. 4. New York: Wiley-Interscience. p 117-212.
15. Szejtli J. 1992. The properties and potential uses of cyclodextrin derivatives. J Incl Phenom 14:25-36.
16. Jicsinszky L, Hashimoto H, Fenyvesi E, Ueno A. 1996. Cyclodextrin derivatives. In: Szejtli J, Osa T, editors. Cyclodextrins. Oxford: Pergamon, p 266-270.
17. Uekama K, Hirayama F, Irie T. 1991. Pharmaceutical uses of cyclodextrin derivatives. In: Szycher M, editor. High performance biomaterials, a comprehensive guide to medical and pharmaceutical applications. Lancaster: Technomic Publishing Co., Inc. p 789-806.
18. Szejtli J. 1998. Introduction and general overview of cyclodextrin chemistry. Chem Rev 98:1743-1753.
19. Loftsson T, Fridriksdóttir H, Sigurdadóttir A, Ueda H. 1994. The effect of water-soluble polymers on drug-cyclodextrin complexation. Int J Pharm 10:169-177.
20. Loftsson T, Fridriksdóttir H, Thórisdóttir S, Stefánsson E. 1994. The effect of hydroxypropyl methylcellulose on the release of dexamethasone from aqueous 2-hydroxypropyl-β-cyclodextrin formulations. Int J Pharm 104:181-184.
21. Loftsson T, Gudmundsdóttir T, Fridriksdóttir H. 1996. The influence of water-soluble polymers and pH on hydroxypropyl-β-cyclodextrin of drugs. Drug Dev Ind Pharm 22:401-405.
22. Krishnamoorthy R, Mitra AK. 1996. Complexation of weak acids and bases with cyclodextrins: Effects of substrate ionization on the estimation and interpretation of association constants. Int J Pharm Adv 1:330-343.
23. Liu F, Kildsig DO, Mitra AK. 1992. Cyclodextrin/ weak-electrolyte complexation: interpretation and estimation of association constants from phase solubility diagrams. Pharm Res 9:1671-1672.
24. Menard FA, Dedhiya MG, Rhodes CT. 1988. Studies on the effect of pH, temperature and ring size on the complexation of phenytoin with cyclodextrins. Pharm Acta Helv 63:303-308.
25. Backensfeld T, Müller B, Kolter K. 1991. Interaction of NSA with cyclodextrins and hydroxypropyl cyclodextrin derivatives. Int J Pharm 74:85-93.
26. Helm H, Müller B, Waaler T. 1995. Complexation of dihydroergotamine mesylate with cyclodextrin derivatives: Solubility and stability in aqueous solution. Eur J Pharm Sci 3:195-201.
27. Tinwalla A, Hoesterey B, Xiang T, Lim K, Anderson B. 1993. Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxypropyl-β-cyclodextrin. Pharm Res 10:1136-1143.
28. Johnson M, Hoesterey B, Anderson B. 1994. Solubilization of a tripeptide HIV protease inhibitor using a combination of ionization and complexation with chemically modified cyclodextrins. J Pharm Sci 83:1142-1146.
29. Okimoto K, Rajewski R, Uekama K, Jona J, Stella V. 1996. The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins. Pharm Res 13:256-264.
30. Stadler Szöke Á, Vikmon M, Szejtli J, Kajtár M. 1985. Fendiline-β-cyclodextrin inclusion complex. J Incl Phenom 3:71-84.
31. Li P, Tabibi SE, Yalkowsky SH. 1998. Combined effect of complexation and pH on solubilization. J Pharm Sci 87:1535-1537.
32. Chiesi P, Ventura P, Pasini M, Szejtli J, Vikmon M, Redenti E. US Patent 5,855,916.
33. Szente L, Szejtli J, Vikmon M, Szemán J, Fenyvesy E, Pasini M, Redenti E, Ventura P. 1995. Solution for insolubility problems of base-type drugs: Multicomponent cyclodextrin complexation. In: Proceedings of the 1st world meeting on pharmaceutics, biopharmaceutics, pharmaceutical technology. Chatenay Malabry (France): APGI. p 579-580.
34. Vikmon M, Szemán J, Szejtli J, Pasini M, Redenti E, Ventura P. 1994. Terfenadine/hydroxy acid/ cyclodextrin complexes. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 480-483.
35. Redenti E, Acerbi D, Poli GL, Rondelli I, Ventura P. unpublished results.
36. Tokumura T, Tsushima Y, Tatsuishi K, Kayano M, Machida Y, Nagai T. 1985. Evaluation of bioavailability upon oral administration of cinnarizine-β-cyclodextrin inclusion complex to beagle dogs. Chem Pharm Bull 33:2962-2967.
37. Tokumura T, Nanba M, Tsushima Y, Tatsuishi K, Kayano M, Machida Y, Nagai T. 1986. Enhancement of bioavailability of cinnarizine from its β-cyclodextrin complex on oral administration with D,L-phenylalanine as competing agent. J Pharm Sci 75:391-394.
38. Gerlóczy A, Vikmon M, Szejtli J, Redenti E, Ventura P. 1999. Mutual solubility enhancement by binary and multicomponent complexation of clomiphene and tamoxifen. In: Proceedings of the 9th international symposium on cyclodextrins. Dordrecht: Kluwer Academic Publishers. p 277-280.
39. Gerlóczy A, Szemán J, Csabai K, Vikmon M, Szejtli J, Ventura P, Pasini M. 1995. Pharmacokinetic study of orally administered ketoconazole and its multicomponent complex on rabbits. In: Proceedings of the 1st world meeting on pharmaceutics, biopharmaceutics, pharmaceutical technology. Chatenay Malabry (France): APGI. p 923-924.
40. Esclusa-Diaz M, Pérez-Marcos MB, Vila-Lato JL, Torres-Labandeira JJ. 1996. Improvement in the dissolution properties of ketoconazole through multicomponent β-cyclodextrin complexation. In: Szejtli J, Szente L, editors. Proceedings of the eighth international symposium on cyclodextrins. Dordrecht: Kluwer Academic Publishers. p 305-308.
41. Esclusa-Diaz MT, Gayo-Otero M, Perez-Marcos MB, Vila-Lato JL, Torres-Labandeira JJ. 1996. Preparation and evaluation of ketoconazole-β-cyclodextrin multicomponent complexes. Int J Pharm 142:183-187.
42. Gerlóczy A, Szemán J, Csabai K, Kolbe I, Jicsinzky L, Acerbi D, Ventura P, Redenti E, Szejtli J. 1996. Pharmacokinetic study of orally administered ketoconazole and its multicomponent complex on rabbits of normal and low gastric acidity. In: Szejtli J, Szente L, editors. Proceedings of the eighth international symposium on cyclodextrins. Dordrecht: Kluwer Academic Publishers. p 515-518.
43. Gerlóczy A, Vikmon M, Szejtli J, Szemán J, Redenti E, Acerbi D. 1998. Correlation of in vitro solubility and in vivo absorption of multicomponent and binary β-cyclodextrin complexes of ketoconazole on the achlorhydric rabbit model. In: Proceedings of the 2nd world meeting on pharmaceutics, biopharmaceutics, pharmaceutical technology. Chatenay Malabry (France): APGI. p 729-730.
44. Szemán J, Vikmon M, Szejtli J, Pasini M, Ventura P. 1994. Multicomponent complexes of astemizole with hydroxyacids and cyclodextrins. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 266-270.
45. Csabai K, Vikmon M, Szejtli J, Pasini M, Ventura P. 1994. Cyclobenzaprine/cyclodextrin complexes. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 476-479.
46. Mura P, Franchi G, Faucci MT, Manderioli A, Bramanti G. 1999. Improvement of econazole solubility in multicomponent systems with cyclodextrins and acids. In: Proceedings of the 9th international symposium on cyclodextrins. Dordrecht: Kluwer Academic Publishers. p 375-378.
47. Fenyvesi E, Vikmon M, Szemán J, Szejtli J, Ventura P, Pasini M. 1994. Enhancement of the drug solubilizing capacity of hydroxypropyl-β-cyclodextrin by ternary complex formation. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 414-418.
48. Pitha J, Hoshino T, Torres-Labandeira J, Irie T. 1992. Preparation of drug:hydroxypropylcyclodextrin complexes by a method using ethanol or aqueous ammonium hydroxide as co-solubilisers. Int J Pharm 80:253-258.
49. Pitha J, Hoshino T. 1992. Effects of ethanol on formation of inclusion complexes of hydroxypropylcyclodextrin with testosterone or with methyl orange. Int J Pharm 80:243-251.
50. Piel G, Evrard B, Fillet M, Llabres G, Delattre L. 1998. Development of a non-surfactant parenteral formulation of miconazole by the use of cyclodextrins. Int J Pharm 169:15-22.
51. Piel G, Evrard B, Van Hess T, Delattre L. 1999. Comparison of the IV pharmacokinetics in sheep of miconazole-cyclodextrin solutions and a micellar solution. Int J Pharm 180:41-45.
52. Piel G, Evrard B, Van Hess T, Llabres G, Delattre L. 1999. Development of a parenteral and of an oral formulation of albendazole with cyclodextrins. S.T.P. Pharma Sci 9:257-260.
53. Kano, K. 1986. Cyclodextrin multicomponent complexes. Dojin Nyusu 36:3.
54. Bello JM, Hurtubise RJ. 1988. Characterization of multicomponent mixtures of polynuclear aromatic hydrocarbons with α-cyclodextrin-induced solid-surface room-temperature luminescence. Anal Chem 60:1285-1290.
55. Coleman AW. 1992. Multicomponent organized molecular assemblies based on amphiphilic cyclodextrins. In: Abstracts of the 7th international symposium on molecular recognition and inclusion. Kyoto, July 26-31.
56. Loukas YL, Jayasekera P, Gregoriadis G. 1995. Novel liposome-based multicomponent systems for the protection of photolabile agents. Int J Pharm 117:85-94.
57. Takisawa N, Shiraham K, Tanaka I. 1993. Interactions of amphiphilic drugs with α-, β-, and γ-cyclodextrins. Colloid Polym Sci 271:499-506.
58. Fini A, Fazio G, Feroci G. 1995. Solubility and solubilization properties on non-steroidal anti-inflammatory drugs. Int J Pharm 126:95-102.
59. Redenti E, Fronza G, Zanol M, Ventura P, Szejtli J, Vikmon M. 1994. Complexes of salts of diphenylmethane derivative drugs with β-cyclodextrins: An explanation of the surprisingly high aqueous solubility of the guest and the host. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 410-413.
60. Redenti E, Savelli G. Results to be published.
61. Muñoz De La Peña A, Ndou TT, Zung JB, Greene KL, Live DH, Warner IM. 1991. Alcohol size as a factor in the ternary complexes formed with pyrene and β-cyclodextrin. J Am Chem Soc 113:1572-1577.
62. Schuette JM, Ndou TT, Muñoz De La Peña A, Mukandan S, Warner IM. 1993. Influence of alcohols on the β-cyclodextrin/acridine complex. J Am Chem Soc 115:292-298.
63. Suzuki M, Ito K, Fushimi C, Tondo K. 1993. A study of cyclodextrin complex formation by a freezing point depression method. Chem Pharm Bull 41: 942.
64. Germain P, Bilial M, De Brauner C. 1995. Beta-cyclodextrin/citric acid complexation equilibrium: Thermodynamic study. Apparent solubility of βCD in aqueous solution of citric acid. Termochim Acta 259:187.
65. Fenyvesi E, Vikmon M, Szemán J, Redenti E, Delcanale M, Ventura P, Szejtli J. 1999. Interaction of hydroxy acids with β-cyclodextrin. J Incl Phenom 33:339-344.
66. Tong WQ, Lach JL, Chin TF, Guillory JK. 1991. Structural effects on the binding of amine drugs with the diphenylmethyl functionality to cyclodextrins. I. A microcalorimetry study. Pharm Res 8: 951-957.
67. Redenti E, Pasini M, Ventura P, Spisni A, Vikmon M, Szejtli J. 1993. Inclusion complex of terfenadine with β-cyclodextrin. J Incl Phenom 15:281-292
68. Redenti E, Ventura P, Fronza G, Selva A, Rivara S, Plazzi V, Mor M. 1999. Experimental and theoretical analysis of the interaction of (±)-cis-Ketoconazole with β-cyclodextrin in the presence of (+)-L-tartaric acid. J Pharm Sci 88:599-607.
69. Selva A, Redenti E, Pasini M, Ventura P, Casetta B. 1995. A study of the salts with organic hydroxyacids of the Terfenadine β-cyclodextrin inclusion complex in solution by ionspray mass spectrometry. J Mass Spectrom 30:219-220.
70. Selva A, Redenti E, Ventura P, Zanol M, Casetta B. A study of β-cyclodextrin-ketoconazole-tartaric acid multicomponent non-covalent association by positive and negative ionspray mass spectrometry. J Mass Spectrom 33:729-734.
71. Bacchi A, Amari G, Redenti E, Pelizzi G. To be published.
72. Kim Y, Oksanen AD, Massefski W, Jr., Blake FJ, Duffy ME, Chrunyk B. 1998. Inclusion complexation of ziprasidone mesylate with β-cyclodextrin sulfobutyl ether. J Pharm Sci 87:1560-1567.
73. Gerlóczy A, Vikmon M, Pasini M, Delcanale M, Ventura P. 1994. Unexpected cyclodextrin complexation behavior of some model compounds containing a piperidine group. In: Osa T, editor. Proceedings of the 7th international cyclodextrins symposium. Tokyo: Komiyama. p 270-274.
74. Csabai K, Vikmon M, Szejlti J, Redenti E, Poli GL, Ventura P. 1998. Complexation of manidipine with cyclodextrins and their derivatives. J Incl Phenom 31:169-178.
75. Gerlóczy A, Vikmon M, Szejtli J. Unpublished results.