Oral Drug Delivery with Cyclodextrins

Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicine: Current and Future Industrial Applications

Volumn , Issue , 2011, Pages 177-196

  Veiga, Francisco ^a   Figueiras, Ana Rita ^a,b   Vieira, Amelia ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF BEIRA INTERIOR   (Portugal)

Author keywords

CDs in oral dosage forms controlled release dosage for plasma drug level time profiles; Drug release profiles based on CD complex and CD conjugate combination; Oral drug delivery with cyclodextrins (CDs) enhancing insoluble drug bioavailability

Indexed keywords

EID: 84886460165     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470926819.ch10     Document Type: Chapter

References (131)

1. Shojaei, A.H., Chang, R.K., Guo, X., Burnside, B.A., Couch, R.A. (2001). Systemic drug delivery via the buccal mucosa route. Pharm. Technol., 1, 70-81.
2. Senel, S., Kremer, M., Katalin, N., Squier, C.A. (2001). Delivery of bioactive peptides and proteins across oral (buccal) mucosa. Curr. Pharm. Biotechnol., 2, 175-186.
3. Loftsson, T., Brewster, M.E., Másson, M. (2004). Role of cyclodextrins in improving oral drug delivery. Am. J. Drug Deliv. 2, 1-15.
4. Challa, R., Ahuja, A., Ali, J., Khar, R.K. (2005). Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech, 6, E329-E357.
5. Hirayama, F., Uekama, K. (1999). Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev., 36, 125-141.
6. Bowen, W.E., Wang, Q., Wuelfing, W.P., Thomas, D.L., Nelson, E.D., Brian Hill, Y.M., Thompson, M., Gallagher, K., Reed, R.A. (2008). A Biopharmaceutical Classification System approach to dissolution: mechanisms and strategies. In: Krishna, R., Lawrence, Yu. Eds., Biopharmaceutics Applications in Drug Development, Springer-Verlag, New York.
7. Amidon, G.L., Lennernas, H., Shah, V.P., Crison, J.R.A. (1995). A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res., 12, 413-420.
8. Ku, M.S. (2008). Use of the Biopharmaceutical Classification System in early drug development. AAPS J., 10, 208-212.
9. U.S., FDA(1995). Guidance for Industry: Immediate Release Solid Oral Dosage Forms: Scale Up and Post Approval Changes. CDER/FDA.
10. Lindenberg, M., Kopp, S., Dressman, J.B. (2004). Classification of orally administered drugs on the World Health Organization model list of essential medicines according to the biopharmaceutics classification system. Eur. J. Pharm. Biopharm., 58, 265-278.
11. Rasheed, A., Ashor Kumar, C.K., Sravanthi, V. (2008). Cyclodextrins as drug carrier molecule: a review. Sci. Pharm., 76, 567-598.
12. Puglisi, G., Santagati, N.A., Ventura, C.A., Pignatello, R., Panico, A.M., Spampinato, S. (1991). Enhancement of 4-biphenylacetic acid bioavailability in rats by its b-cyclodextrin complex after oral administration. J. Pharm. Pharmacol., 43, 430-432.
13. Puglisi, G., Ventura, C.A., Spadaro, A., Campana, G., Spampinato, S. (1995). Differential-effects of modified b-cyclodextrins om pharmacological activity and bioavailability of 4-biphenylacetic acid in rats after oral administration. J. Pharm. Pharmacol., 47, 120-123.
14. Ahn, H.J., Kim, K.M., Choi, J.S., Kim, C.K. (1997). Effects of cyclodextrin derivatives on bioavailability of ketoprofen. Drug Dev. Ind. Pharm., 23, 397-401.
15. Miyaji, T., Inoue, Y., Acarturk, F., Imai, T., Otagiri, M., Uekama, K. (1992). Improvement of oral bioavailability of fenbufen by cyclodextrin complexation. Acta Pharm. Nord., 4, 17-22.
16. Ahuja, N., Singh, A., Singh, B. (2003). Rofecoxib: an update on physicochemical, pharmaceutical, pharmacodynamic and pharmacokinetic aspects. J. Pharm. Pharmacol., 55, 859-894.
17. Savolainen, J., Jarvinen, K., Hatilain, L., Jarvinen, T. (1998). Improved dissolution and bioavailability of phenytoin by sulfobutylether-b-cyclodextrin and hydroxypropyl-b-cyclodextrin complexation. Int. J. Pharm., 165, 69-78.
18. Tanino, T., Ogiso, T., Iwaki, M. (1999). Effect of sugarmodified b-cyclodextrins on dissolution and absorption characteristics of phenytoin. Biol. Pharm. Bull., 22, 298-304.
19. Peeters, J., Neeskens, P., Tollenaere, J.P., Remoortere, P.V., Brewster, M.E. (2002). Characterization of the interaction of 2-hydroxypropyl-b-cyclodextrin with itraconazole at pH 2, 4 and 7. J. Pharm. Sci., 91, 1414-1422.
20. Chowdary, K.P.R., Kamalakara, R.G. (2003). Controlled release of nifedipine from mucoadhesive tablets of its inclusion complexes with b-cyclodextrin. Pharmazie, 58, 721-724.
21. Emara, L.H., Badr,R.M.,Abd Elbary, A. (2002). Improving the dissolution and bioavailability of nifedipine using solid dispersions and solubilizers. Drug Dev. Ind. Pharm., 28, 795-807.
22. Carrier, R.L., Miller, L.A., Ahmed, I. (2007). The utility of cyclodextrins for enhancing oral bioavailability. J. Control. Release, 123, 78-99.
23. Fromming, K.-H., Wedelich, V., Mehnert, W. (1984). Influence of cyclodextrins on nitrosation of drugs. J. Inclusion Phenom. Macrocyclic Chem., 2, 605-611.
24. Chavanpatil, M., Vavia, P.R. (2002). Enhancement of nasal absorption of acyclovir via cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem., 44, 137-144.
25. Huang, L., Taylor, H., Gerber, M., Orndorff, P.E., Horton, J.R., Tonelli, A. (1999). Formation of antibiotic, biodegradable/bioabsorbable polymers by processing with neomycin sulfate and its inclusion compound with b-cyclodextrin. J. Appl. Polym. Sci., 74, 937-947.
26. Ikeda,Y., Motoune, S., Matsuoka, T., Arima, H., Hirayama, F., Uekama, K. (2002). Inclusion complex formation of captopril with a-and b-cyclodextrins in aqueous solution: NMR spectroscopic and molecular dynamic studies. J. Pharm. Sci., 91, 2390-2398.
27. Ran, Y., Zhao, L., Xu, Q., Yalkowsky, S.H. (2001). Solubilization of cyclosporin A. AAPS PharmSciTech, 2, 1-4.
28. Sharma, P., Varma, M.V.S., Chawla, H.P.S., Panchagnula, R. (2005). Relationship between lipophilicity of BCS class III and IV drugs and the functional activity of peroral absorption enhancers. Il Farmaco, 60, 870-873.
29. Lipinski, C.A. (2000). Drug-like properties and the cause of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods, 44, 235-249.
30. Másson, M., Loftsson, T., Másson, G., Stefánsson, E. (1999). Cyclodextrins as permeation enhancers: some theoretical evaluations and in vitro testing. J. Control. Release, 59, 107-118.
31. Matilainen, L., Toropainen, T., Vihola, H., Hirvonen, J., Jarvinen, T., Jarho, P., Jarvinen, K. (2008). In vitro toxicity and permeation of cyclodextrins in Calu-3 cells. J. Control. Release, 126, 10-16.
32. Loftsson, T., Sigfússon, S.D., Sigurosson, H.H., Másson, M. (2003). The effects of cyclodextrins on topical delivery of hydrocortisone: the aqueous diffusion layer. STP Pharma Sci., 13, 125-131.
33. Irie, T., Uekama, K. (1997). Pharmaceutical applications of cyclodextrins: III. Toxicological issues and safety evaluation. J. Pharm. Sci., 86, 147-161.
34. Uekama, K., Hirayama, F., Irie, T. (1998). Cyclodextrin drug carrier systems. Chem. Rev., 98, 2045-2076.
35. Matsuda, H., Arima, H. (1999). Cyclodextrins in transdermal and rectal delivery. Adv. Drug Deliv. Rev. 36, 81-99.
36. Loftsson, T.,Másson, M. (2001). Cyclodextrins in topical drug formulations: theory and practice. Int. J. Pharm., 225, 15-30.
37. Loftsson, T., Jarho, P., Másson, M., Jarvinen, K. (2005). Cyclodextrins in drug delivery. Expert Opin. Drug Deliv. 2, 335-351.
38. Loftsson, T., Bodor, N. (1995) Percutaneous Penetration Enhancers, CRC Boca Raton, FL.
39. Irie, T., Wakamatsu, K., Arima, H., Aritomi, H., Uekama, K. (1992). Enhancing effects of cyclodextrins on nasal absorption of insulin in rats. Int. J. Pharm., 84, 129-139.
40. Loftsson, T. (1998). Cyclodextrins in pharmaceutical formulations: the effect of polymers on their complexation efficacy and drug availability. Report prepared for the Nordic Industrial Fund.
41. Loftsson, T., Hreinsdóttir, D., Másson, M. (2007). The complexation efficiency. J. Inclusion Phenom. Macrocyclic Chem. 57, 545-552.
42. Li, P., Tabibi, E., Yalkowsky, S.H. (1998). Combined effect of complexation pH on solubilization. J. Pharm. Sci., 87, 1535-1537.
43. Loftsson, T., Duchêne, D. (2007). Cyclodextrins and their pharmaceutical applications. Int. J. Pharm., 329, 1-11.
44. Hanna, K., Brauer, C.H., Germain, P. (2004). Cyclodextrinenhanced solubilization of pentachlorophenol in water. J. Environ. Manag., 71, 1-8.
45. Zornoza, A., Martín, C., Sánchez, M., Piquer, A. (1998). Inclusion complexation of glisentide with a-, b-and c-cyclodextrins. Int. J. Pharm., 169, 239-244.
46. Loftsson, T., Ólafsdóttir, B.J., Frioriksdóttir, H., Jónsdóttir, S. (1993). Cyclodextrin complexation of NSAIDs: physicochemical characteristics. Eur. J. Pharm. Sci., 1, 95-101.
47. Granero, G., Granero, C., Longhi, M. (2003). The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-b-cyclodextrin. Eur. J. Pharm. Sci., 20, 285-293.
48. Loftsson, T., Sigurosson, H.H., Másson, M., Schipper, N. (2004). Preparation of solid drug/cyclodextrin complexes of acidic and basic drugs. Pharmazie, 59, 25-29.
49. Redenti, E., Szene, L., Szejtli, J. (2001). Cyclodextrin complexes of salts of acidic drugs: thermodynamic properties, structural features, and pharmaceutical applications. J. Pharm. Sci., 90, 979-986.
50. Esclusa-Díaz, M.T., Gayo-Otero, M., Pérez-Marcos, M.B., Vila-Jato, J.L., Torres-Labandeira, J.J. (1996). Preparations and evaluation of ketoconazole-b-cyclodextrin multicomponent complexes. Int. J. Pharm., 142, 183-187.
51. Ribeiro, L., Carvalho, R.A., Ferreira, D.C., Veiga, F.J.B. (2005). Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water-soluble polymers monitored byNMRand solubility studies. Eur. J. Pharm. Sci., 24, 1-13.
52. Redenti, E., Ventura, P., Fronza, G., Selva, A., Rivara, S., Plazzi, P.V., Mor, M. (1999). Experimental and theoretical analysis on the interaction of (+/-)-cis-ketoconazole with b-cyclodextrin in the presence of ({thorn})-L-tartaric acid. J. Pharm. Sci., 88, 599-607.
53. Faucci, M.T., Melani, F., Mura, P. (2000). H-NMR and molecular modeling techniques for the investigation of the inclusion complex of econazole with a-cyclodextrin in the presence of malic acid. J. Pharm. Biomed. Anal., 23, 25-31.
54. Redenti, E., Szente, L., Szejtli, J. (2000). Drug/cyclodextrin/hydroxy acid multicomponent systems: properties and pharmaceutical applications. J. Pharm. Sci., 89, 1-8.
55. Piel, G., Pirotte, B., Delneuville, I., Neven, P., Llabres, G., Delarge, J., Delattre, L. (1997). Study of the influence of both cyclodextrins and L-lysine on the aqueous solubility of nimesulide; isolation and characterization of nimesulide-Llysine-cyclodextrin complexes. J. Pharm. Sci., 86, 475-480.
56. Mura, P., Maestrelli, F., Cirri, M. (2003). Ternary systems of naproxen with hydroxypropyl-b-cyclodextrin and aminoacids. Int. J. Pharm., 260, 293-302.
57. Figueiras, A., Sarragu̧ca, J.M.G., Carvalho, R.A., Pais, A.A.C. C., Veiga, F.J.B. (2007). Interaction of omeprazole with a methylated derivative of b-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation. Pharm. Res., 24, 377-389.
58. Riley, C.M., Rytting, J.H., Kral, M.A. (1991) Takeru Higuhi, a memorial tribute: equilibria and thermodynamics. Kansas.
59. Loftsson, T., Fridriksdottir, H., Gudmundsdottir, T.K. (1996). The effect of water -soluble polymers on aqueous solubility of drugs. Int. J. Pharm., 127, 293-296.
60. Loftsson, T., Fridriksdóttir, H. (1998). The effect of watersoluble polymers on the aqueous solubility and complexing abilities of b-cyclodextrin. Int. J. Pharm., 163, 115-121.
61. Granero, G., Longhi, M. (2002). Thermal analysis and spectroscopy characterization of interactions between a naphthoquinone derivative with HP-beta-cyclodextrins and PVP. Pharm. Dev. Technol., 7, 381-390.
62. Rácz, I. (1989). Drug Formulation. Budapest, Hungary, pp. 212-242.
63. Mura, P., Faucci, M.T., Bettinetti, G.P. (2001). The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-b-cyclodextrin. Eur. J. Pharm. Sci., 13, 187-194.
64. Loftsson, T. (1998). Increasing the cyclodextrin complexation of drugs and drug bioavailability through addition of watersoluble polymers. Pharmazie, 53, 733-740.
65. Duan, M., Zhao, N., Ossurardóttir, I.B., Thorsteinsson, T., Loftsson, T. (2005). Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarban: formation of aggregates and higher-order complexes. Int. J. Pharm., 297, 213-222.
66. Loftsson, T., Másson, M., Brewster, E.M. (2004). Selfassociation of cyclodextrins and cyclodextrin complexes. J. Pharm. Sci., 93, 1091-1099.
67. Loftsson, T., Matthíasson, K.,Másson, M. (2003). The effects of organic salts on the cyclodextrin solubilization of drugs. Int. J. Pharm., 262, 101-107.
68. Qiu, Y., (2009). Rational design of oral modified-release drug delivery systems. In: Qiu, Y., Chen, Y., Zharg, G., Liu, L., Porter, W., Eds., Developing Solid Oral Dosage Forms. Academic Press, San Diego, CA, pp. 469-499.
69. Martin Del Valle, E.M. (2004). Cyclodextrins and their uses: a review. Process Biochem., 39, 1033-1046.
70. Brewster, M.E., Loftsson, T. (2007). Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev., 59, 645-666.
71. Vyas, A., Saraf, S., Saraf, S. (2008). Cyclodextrin based novel drug delivery systems. J. Inclusion Phenom. Macrocyclic Chem. 62, 23-42.
72. Stella,V.J., He, Q. (2008). Cyclodextrins. Toxicol. Pathol. 36, 30-42.
73. Figueiras, A., Carvalho, R.A., Ribeiro, L., Torres-Labandeira, J.J., Veiga, F.J.B. (2007). Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified b-cyclodextrin. Eur. J. Pharm. Biopharm., 67, 531-539.
74. Zingone, G., Rubessa, F. (2005). Preformulation study of the inclusion complex warfarin-b-cyclodextrin. Int. J. Pharm., 291, 3-10.
75. Hirlekar, R., Kadam, V. (2009). Preparation and characterization of inclusion complexes of carvedilol with methylb-cyclodextrin. J. Inclusion Phenom. Macrocyclic Chem., 63, 219-224.
76. Sathigari, S., Chadha, G., Lee,Y.-H.P., Wright, N., Parsons, D. L., Rangari, V.K., Fasina, O., Babu, R.J. (2009). Physicochemical characterization of efavirenz-cyclodextrin inclusion complexes. AAPS PharmSciTech, 10, 81-87.
77. Fernandes, C.M., Vieira, M.T., Veiga, F.J.B. (2002). Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds. Eur. J. Pharm. Sci., 15, 79-88.
78. Badr-Eldin, S.M., Elkheshen, S.A., Ghorab, M.M. (2008). Inclusion complexes of tadalafil with natural and chemically modified b-cyclodextrins. I: Preparation and in-vitro evaluation. Eur. J. Pharm. Biopharm., 70, 819-827.
79. Cunha-Filho, M.S.S., Dacunha-Marinho, B., Torres-Labandeira, J.J., Martínez-Pacheco, R., Landín, M. (2009). Characterization of b-lapachone and methylated b-cyclodextrin solid-state systems. AAPS PharmSciTech, 8, E68-E77.
80. Evrard, B., Chiap, P., DeTullioc, P., Ghalmid, F., Piela, G.,Van Heesa, T., Crommen, J., Losson, B., Delattre, L. (2002). Oral bioavailability in sheep of albendazole from a suspension and from a solution containing hydroxypropyl-b-cyclodextrin. J. Control. Release, 85, 45-50.
81. Veiga, F., Fernandes, C., Teixeira, F. (2000). Oral bioavailability and hypoglycaemic activity of tolbutamide/cyclodextrin inclusion complexes. Int. J. Pharm., 202, 165-171.
82. Bibby, D.C., Davies, N.M., Tucker, I.G. (2000). Mechanisms by which cyclodextrins modify drug release from polymeric drug delivery systems. Int. J. Pharm., 197, 1-11.
83. Rao, V.M., Haslam, J.L., Stella, V.J. (2001). Controlled and complete release of a model poorly water-soluble drug, prednisolone, from hydroxypropyl methylcellulose matrix tablets using (SBE)7b-cyclodextrin as a solubilizing agent. J. Pharm. Sci., 90, 807-816.
84. Koester, L.S., Xavier, C.R., Mayorga, P., Bassani, V.L. (2003). Influence of b-cyclodextrin complexation on carbamazepine release from hydroxypropyl methylcellulose matrix tablets. Eur. J. Pharm. Biopharm., 55, 85-91.
85. Pose-Vilarnovo, B., Rodríguez-Tenreiro, C., Santos, J.F.R., Vázquez-Doval, J., Concheiro, A., Alvarez-Lorenzo, C., Torres-Labandeira, J.J. (2004). Modulating drug release with cyclodextrins in hydroxypropyl methylcellulose gels and tablets. J. Control. Release, 94, 351-363.
86. Sangalli,M.E., Zema, L.,Maroni,A., Foppoli, A.,Giordano, F., Gazzaniga, A. (2001). Influence of b-cyclodextrin on the release of poorly soluble drugs from inert and hydrophilic heterogeneous polymeric matrices. Biomaterials, 22, 2647-2651.
87. Cappello, B., De Rosa, G., Giannini, L., La Rotonda, M.I., Mensitieri, G., Miro, A., Quaglia, F., Russo, R. (2006). Cyclodextrin-containing poly(ethyleneoxide) tablets for the delivery of poorly soluble drugs: potential as buccal delivery system. Int. J. Pharm., 319, 63-70.
88. Miro, A., Rondinone, A., Nappi, A., Ungaro, F., Quaglia, F., La Rotonda, M.I. (2009). Modulation of release rate and barrier transport of diclofenac incorporated in hydrophilic matrices: role of cyclodextrins and implications in oral drug delivery. Eur. J. Pharm. Biopharm., 72, 76-82.
89. Lemesle-Lamache, V., Wouessidjewe, D., Chéron, M., Duchêne, D. (1996). Study of b-cyclodextrin and ethylated b-cyclodextrin salbutamol complexes, in vitro evaluation of sustained-release behaviour of salbutamol. Int. J. Pharm., 141, 117-124.
90. Fernandes, C.M., Veiga, F.J.B. (2002). Effect of the hydrophobic nature of triacetyl-b-cyclodextrin on the complexation with nicardipine hydrochloride: physicochemical and dissolution properties of the kneaded and spray-dried complexes. Chem. Pharm. Bull., 50, 1597-1602.
91. Corti, G., Capasso, G., Maestrelli, F., Cirri, M., Mura, P. (2007). Physical-chemical characterization of binary systems of metformin hydrochloride with triacetyl-b-cyclodextrin. J. Pharm. Biomed. Anal., 45, 480-486.
92. Filípovicacute;-Grcicacute;, J., Becirevic-Lacan, M., Skalko, N., Jalsenjak, I. (1996). Chitosan microspheres of nifedipine and nifedipine-cyclodextrin inclusion complexes. Int. J. Pharm., 135, 183-190.
93. Quaglia, F., Varricchio, G., Miro, A., La Rotonda, M.I., Larobina, D., Mensitieri, G. (2001). Modulation of drug release from hydrogels by using cyclodextrins: the case of nicardipine/b-cyclodextrin system in crosslinked polyethylenglycol. J. Control. Release, 71, 329-337.
94. Ikeda,Y., Motoune, S., Marumoto, S., Sonoda,Y., Hirayaama, F., Arima, H., Uekama, K. (2004). Effect of 2-hydroxypropylb-cyclodextrin on release rate of metoprolol from ternary metoprolol/2-hydroxypropyl-b-cyclodextrin/ethylcellulose Tablets. J. Inclusion Phenom. Macrocyclic Chem., 44, 141-144.
95. Uekama, K., Horikawa, T., Horiuchi, Y., Hirayama, F. (1993). In vitro and in vivo evaluation of delayed-release behavior of diltiazem from its O-carboxymethyl-O-ethyl-b-cyclodextrin complex. J. Control. Release, 25, 99-106.
96. Horikawa, T., Hirayama, F., Uekama, K. (1995). In-vivo and in-vitro correlation for delayed-release behaviour of a molsidomine/O-carboxymethyl-O-ethyl-b-cyclodextrin complex in gastric acidity-controlled dogs. J. Pharm. Pharmacol., 47, 124-127.
97. Uekama, K. (2004). Design and evaluation of cyclodextrinbased drug formulation. Chem. Pharm. Bull., 52, 900-915.
98. Uekama, K., Minami, K., Hirayama, F. (1997). 6A-O-[(4-Biphenylyl)acetyl]-a-, b-, and -c-cyclodextrins and 6Adeoxy-6A-[[(4-biphenylyl)acetyl]amino]-a-, b-, and c-cyclodextrins: potential prodrugs for colon-specific delivery. J. Med. Chem. 40, 2755-2761.
99. Minami, U., Hirayama, F., Uekama, K. (1998). Colon-specific drug delivery based on a cyclodextrin prodrug: release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration. J. Pharm. Sci., 87, 715-720.
100. Hirayama, F., Ogata, T.,Yano, H., Arima, H., Udo, K., Takano, M., Uekama, K. (2000). Release characteristics of a shortchain fatty acid, n-butyric acid, from its b-cyclodextrin ester conjugate in rat biological media J. Pharm. Sci., 89, 1486-1495.
101. Feng Cao, Y.R.,Weiyi, H. (2009). Cyclomaltoheptaose mixed esters of anti-inflammatory drugs and short-chain fatty acids and study of their enzymatic hydrolysis in vitro. Carbohydr. Res., 344, 526-530.
102. Yano, H., Hirayama, F., Kamada, M., Arima, H., Uekama, K. (2002). Colon-specific delivery of prednisolone-appended a-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J. Control. Release, 79, 103-112.
103. Kamada, M., Hirayama, F., Udo, K., Yano, H., Arima, H., Uekama, K. (2002). Cyclodextrin conjugate-based controlled release system: repeated-and prolonged-releases of ketoprofen after oral administration in rats. J. Control. Release, 82, 407-416.
104. El-Kamel, A.H., Abdel-Aziz, A.A.-M., Arnal, J., Fatani, A.J., El-Subbagh, H.I. (2008). Oral colon targeted delivery systems for treatment of inflammatory bowel diseases: synthesis, in vitro and in vivo assessment. Int. J. Pharm., 358, 248-255.
105. Zou, M., Okamoto, H., Cheng, G., Hao, X., Sun, J., Cui, F., Danjo, K. (2005). Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems. Eur. J. Pharm. Biopharm., 59, 155-160.
106. Dev, S., Mhaske, D.V., Kadam, S.S., Dhaneshwar, S.R. (2007). Synthesis and pharmacological evaluation of cyclodextrin conjugate prodrug of mefenamic acid. Indian J. Pharm. Sci., 69, 69-72.
107. Fernandes, C.M., Ramos, P., Falcão, A.C., Veiga, F.J.B. (2003). Hydrophilic and hydrophobic cyclodextrins in a new sustained release oral formulation of nicardipine: in vitro evaluation and bioavailability studies in rabbits. J. Control. Release, 88, 127-134.
108. Fernandes, C.M., Veiga, F.J.B. (2002). The cyclodextrins as modelling agents of drug controlled release. J. Inclusion Phenom. Macrocyclic Chem. 44, 79-85.
109. Ikeda, Y., Kimura, K., Hirayama F., Arima, H., Uekama, K. (2000). Controlled release of a water-soluble drug, captopril, by a combination of hydrophilic and hydrophobic cyclodextrin derivatives. J. Control. Release, 66, 271-280.
110. Wang, Z., Hirayama, F., Ikegami, K., Uekama, K. (1993). Release characteristics of nifedipine from 2-hydroxypropylb-cyclodextrin complex during storage and its modification of hybridizing polyvinylpyrrolidone K-30. Chem. Pharm. Bull., 45, 1822-1826.
111. Zheng, W., Horikawa, T., Hirayama, T., Hirayama, F., Uekama, K. (1993). Design and in-vitro evaluation of a modifiedrelease oral dosage form of nifedipine by hybridization of hydroxypropyl-b-cyclodextrin and hydroxypropylcellulose. J. Pharm. Pharmacol., 45, 942-946.
112. Okimoto, K., Tokunaga, Y., Ibuki, R., Irie, T., Uekama, K., Rajewski, R.A., Stella,V.J. (2004). Applicability of (SBE)7mb-CD in controlled-porosity osmotic pump tablets (OPTs). Int. J. Pharm. 286, 81-88.
113. Okimoto, K., Rajewski, R.A., Stella, V.J. (1999). Release of testosterone from an osmotic pump tablet utilizing (SBE)7mb-cyclodextrin as both a solubilizing and an osmotic pump agent. J. Control. Release, 58, 29-38.
114. Zannou, E.A., Streng, W., Stella, V.J. (2001). Osmotic properties of sulfobutylether and hydroxypropyl cyclodextrins. Pharm. Res., 18, 1226-1231.
115. Harrs, D., Robinson, J.R. (1992). Drug delivery via the mucous membranes of the oral cavity. J. Pharm. Sci., 82, 1-10.
116. Jain, A.C., Aungst, B.J., Adeyeye, M.C. (2002). Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 b-cyclodextrin (SBE 7) complexes. J. Pharm. Sci., 91, 1659-1668.
117. Jug, M., Bećirević-Laćan, M. (2004). Influence of hydroxypropyl-b-cyclodextrin complexation on piroxicam release from buccoadhesive tablets. Eur. J. Pharm. Sci., 21, 251-260.
118. Hoon, T.J., Dawood, M.Y., Khan-Dawood, F.S., Ramos, J., Batenhorst, R.L. (1993). Bioequivalence of 17 b-estradiol hydroxypropyl-b-cyclodextrincomplex in postmenopausal women. J. Clin. Pharmacol., 33, 1116-1121.
119. Brown, G.A., Martin, E.R., Roberts, B.S., Vukovich, M.D., King, D.S. (2002). Acute hormonal response to sublingual androstenediol in young men. J. Appl. Physiol., 92, 142-146.
120. Yoo, S.D., Yoon, B.M., Lee, H.S., Lee, K.C. (1999). Increased bioavailability of clomipramine after sublingual administration in rats. J. Pharm. Sci., 88, 1119-1121.
121. Badawy, S.I.F., Ghorab, M.M., Adeyeye, C.M. (1996). Bioavailability of danazolhydroxypropyl-b-cyclodextrin complex by different routes of administration. Int. J. Pharm., 145, 137-143.
122. Mannila, J., Jarvinen, T., Jarvinen, K., Tarvainen, M., Jarho, P. (2005). Effects of RM-b-CD on sublingual biovailability of D9-tetrahydrocannabinol in rabbits. Eur. J. Pharm. Sci., 26, 71-77.
123. Boulmedarat, L., Bochot, A., Lesieur, S., Fattal, E. (2005). Evaluation of buccal methyl-b-cyclodextrin toxicity on human oral epithelial cell culture model. J. Pharm. Sci., 94, 1300-1309.
124. Merkus, F.W.H.M., Verhoef, J.C., Marttin, E., Romeijn, S.G., van der Kuy, P.H.M., Hermens, W.A.J.J., Schipper, N. G. M. (1999). Cyclodextrins in nasal drug delivery. Adv. Drug Deliv. Rev. 36, 41-57.
125. Szejtli, J. (2004). Past, present, and future of cyclodextrin research. Pure Appl. Chem., 76, 1825-1845.
126. Loftsson, T., Ducĥene, D. (2007). Historical perspectives: cyclodextrins and their pharmaceutical applications. Int. J. Pharm., 329, 1-11.
127. Loftsson, T., Kristmundsdóttir, T., Ingvvarsdóttir, K., Ólafsdóttir, B.J., Baldvinsdóttir, J. (1992). Preparation and physical evaluation of micorcapsules of hydrophilic drug-cyclodextrin complexes. J. Microencapsul. 9, 375-382.
128. Soares, F.A., Carvalho, R.A., Veiga, F. (2007). Oral administration of peptides and porteins: nanoparticles and cyclodextrins as biocompatible delivery systems. Nanomedicine, 2, 183-202.
129. Irie, T., Uekama, K. (1999). Cyclodextrins in peptide and protein delivery. Adv. Drug Deliv. Rev., 36, 101-123.
130. Hattori, K. (2007). Synthesis and evaluation of novel targeting cyclodextrins as drug carrier. Presented at the 4th Asian Cyclodextrin Conference.
131. Eguchi, M., Yong-Zhong, D., Ogawa, Y., Okada, T., Yumoto, N., Kodaka, M. (2006). Effects of conditions for preparing nanoparticles composed of aminoethylcarbamoyl-b-cyclodextrin and ethylene glycol diglycidyl ether on trap efficiency of a guest molecule. Int. J. Pharm., 311, 215-222.