Cyclodextrin-Enhanced Drug Delivery through Mucous Membranes

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

Volumn , Issue , 2011, Pages 145-158

  Jansook, Phatsawee ^a   Brewster, Marcus E ^b   Loftsson, Thorsteinn ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

Cyclodextrin enhanced drug delivery through mucous membranes; Membrane properties and effect of CDs on drug flux through membranes; Pulmonary drug delivery respiratory mucosa, much lower resistance toward drug permeation

Indexed keywords

EID: 84872775086     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470926819.ch8     Document Type: Chapter

References (112)

1. Smart, J.D. (2005). The basics and underlying mechanisms of mucoadhesion. Adv. Drug Deliv. Rev., 57, 1556-1568.
2. Ahuja, A., Khar, R.K., Ali, J. (1997). Mucoadhesive drug delivery systems. Drug Dev. Ind. Pharm., 23, 489-515.
3. Senel, S., Hincal, A.A. (2001). Drug permeation enhancement via buccal route: possibilities and limitations. J. Controll. Release, 72, 133-144.
4. Brewster, M.E., Noppe, M., Peeters, J., Loftsson, T. (2007). Effect of the unstirred water layer on permeability enhancement by hydrophilic cyclodextrins. Int. J. Pharm., 342, 250-253.
5. Shah, P., Jogani, V., Mishra, P., Mishra, A.K., Bagchi, T., Misra, A. (2007). Modulation of ganciclovir intestinal absorption in presence of absorption enhancers. J. Pharm. Sci., 96, 2710-2722.
6. Cu, Y., Saltzman, W.M. (2009). Mathematical modeling of molecular diffusion through mucus. Adv. Drug Deliv. Rev., 61, 101-114.
7. Prego, C., Garcia, M., Torres, D., Alonso, M.J. (2005). Transmucosal macromolecular drug delivery. J. Controll. Release, 101, 151-162.
8. Cone, R.A. (2009). Barrier properties of mucus. Adv. Drug Deliv. Rev., 61, 75-85.
9. Lai, S.K., Wang, Y.Y., Hanes, J. (2009). Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues. Adv. Drug Deliv. Rev., 61, 158-171.
10. Khanvilkar, K., Donovan, M.D., Flanagan, D.R. (2001). Drug transfer through mucus. Adv. Drug Deliv. Rev., 48, 173-193.
11. Salamat-Miller, N., Chittchang, M., Johnston, T.P. (2005). The use of mucoadhesive polymers in buccal drug delivery. Adv. Drug Deliv. Rev., 57, 1666-1691.
12. Brewster, M.E., Loftsson, T. (2007). Cyclodextrins as pharmaccutical solubilizers. Adv. Drug Deliv. Rev., 59, 645-666.
13. Loftsson, T., Duchêne, D. (2007). Cyclodextrins and their pharmaceutical applications. Int. J. Pharm., 329, 1-11.
14. Loftsson, T., Bodor, N. (1995). Percutaneous Penetration Enhancers. CRC Press, Boca Raton, FL, pp. 335-341.
15. Shimpi, S., Chauhan, B., Shimpi, P. (2005). Cyclodextrins: application in different routes of drug administration. Acta Pharma., 55, 139-156.
16. He, Y.F., Fu, P., Shen, X.H., Gao, H.C. (2008). Cyclodextrinbased aggregates and characterization by microscopy. Micron, 39, 495-516.
17. Jansook, P., Kurkov, S.V., Loftsson, T. (2010). Cyclodextrin as solubilizers: formation of complex aggregates. J. Pharm. Sci., 99, 719-729.
18. Lai, S.K., O'Hanlon, D.E., Harrold, S., Man, S.T., Wang, Y.Y., Cone, R., Hanes, J. (2007). Rapid transport of large polymeric nanoparticles in fresh undiluted human mucus. Proc. Natl. Acad. Sci. USA, 104, 1482-1487.
19. Maleki, A., Lafitte, G., Kjoniksen, A.L., Thuresson, K., Nystrom, B. (2008). Effect of pH on the association behavior in aqueous solutions of pig gastric mucin. Carbohydr. Res., 343, 328-340.
20. Loftsson, T., Sigurdsson, H.H., Konradsdóttir, F., Gisladóttir, S., Jansook, P., Stefánsson, E. (2008). Topical drug delivery to the posterior segment of the eye: anatomical and physiological considerations. Pharmazie, 63, 171-179.
21. Lai, S.K., Wang, Y.Y., Wirtz, D., Hanes, J. (2009). Microand macrorheology of mucus. Adv. Drug Deliv. Rev., 61, 86-100.
22. Loftsson, T., Jarho, P., Másson, M., Järvinen, T. (2005). Cyclodextrins in drug delivery. Expert Opin. Drug Deliv., 2, 335-351.
23. Loftsson, T., Vogensen, S.B., Brewster, M.E., Konradsdóttir, F. (2007). Effects of cyclodextrins on drug delivery through biological membranes. J. Pharm. Sci., 96, 2532-2546.
24. Loftsson, T., Stefánsson, E. (2007). Cyclodextrins in ocular drug delivery: theoretical basis with dexamethasone as a sample drug. J. Drug Deliv. Sci. Technol., 17, 3-9.
25. Jarho, P., Urtti, A., Pate, D.W., Suhonen, P., Järvinen, T. (1996). Increase in aqueous solubility, stability and in vitro corneal permeability of anandamide by hydroxypropyl-β-cyclodextrin. Int. J. Pharm., 137, 209-216.
26. Bary, A.R., Tucker, I.G., Davies, N.M. (2000). Considerations in the use of hydroxypropyl-β-cyclodextrin in the formulation of aqueous ophthalmic solutions of hydrocortisone. Eur. J. Pharm. Biopharm., 50, 237-244.
27. Richter, T., Keipert, S. (2004). In vitro permeation studies comparing bovine nasal mucosa, porcine cornea and artificial membrane: androstenedione in microemulsions and their components. Eur. J. Pharm. Biopharm., 58, 137-143.
28. Washington, N., Washington, W.C., Wilson C.G. (2001). Physiological Pharmaceutics: Barriers to Drug Absorption. Taylor & Francis, London, pp. 37-58, 109-142, 221-270.
29. Mannermaa, E., Vellonen, K.S., Urtti, A. (2006). Drug transport in corneal epithelium and blood-retina barrier: emerging role of transporters in ocular pharmacokinetics. Adv. Drug Deliv. Rev., 58, 1136-1163.
30. Kublik, H., Bock, T.K., Schreier, H., Müller, B.W. (1996). Nasal absorption of 17-β-estradiol from different cyclodextrin inclusion formulations in sheep. Eur. J. Pharm. Biopharm., 42, 320-324.
31. Lennernas, H. (1998). Human intestinal permeability. J. Pharm. Sci., 87, 403-410.
32. Somogyi, G., Posta, J., Buris, L., Varga, M. (2006). Cyclodextrin (CD) complexes of cholesterol: their potential use in reducing dietary cholesterol intake. Pharmazie, 61, 154-156.
33. 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.
34. 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.
35. Matsuda, H., Arima, H. (1999). Cyclodextrins in transdermal and rectal delivery. Adv. Drug Deliv. Rev., 36, 81-99.
36. Loftsson, T., Järvinen, T. (1999). Cyclodextrins in ophthalmic drug delivery. Adv. Drug Deliv. Rev., 36, 59-79.
37. Hussain, A., Arnold, J.J., Khan, M.A., Ahsan, F. (2004). Absorption enhancers in pulmonary protein delivery. J. Controll. Release, 94, 15-24.
38. Ammar, H.O., El-Nahhas, S.A., Khalil, R.M. (1998). Cyclodextrins in acetazolamide eye drop formulations. Pharmazie, 53, 559-562.
39. Loftsson, T., Fridriksdóttir, H., Thórisdóttir, S., Stefánsson, E., Sigurdardóttir, A.M., Gudmundsson, O., Sigthórsson, T. (1994). 2-Hydroxypropyl-β-cyclodextrin in topical carboni-c-anhydrase inhibitor formulations. Eur. J. Pharm. Sci., 1, 175-180.
40. Loftsson, T., Stefánsson, E., Kristinsson, J.K., Fridriksdóttir, H., Sverrisson, T., Gudmundsdóttir, G., Thórisdóttir, S. (1996). Topically effective acetazolamide eye-drop solution in man. Pharm. Sci., 2, 277-279.
41. Usayapant, A., Karara, A.H., Narurkar, M.M. (1991). Effect of 2-hydroxypropyl-β-cyclodextrin on the ocular absorption of dexamethasone and dexamethasone acetate. Pharm. Res., 8, 1495-1499.
42. Loftsson, T., Stefánsson, E. (2002). Cyclodextrins in eye drop formulations: enhanced topical delivery of corticosteroids to the eye. Acta Ophthalmol. Scand., 80, 144-150.
43. Sigurdsson, H.H., Konradsdóttir, F., Loftsson, T., Stefánsson, E. (2007). Topical and systemic absorption in delivery of dexamethasone to the anterior and posterior segments of the eye. Acta Ophthalmol. Scand., 85, 598-602.
44. Kristinsson, J.K., Fridriksdóttir, H., Thorisdóttir, S., Sigurdardóttir, A.M., Stefánsson, E., Loftsson, T. (1996). Dexamethasone-cyclodextrin-polymer co-complexes in aqueous eye drops: aqueous humor pharmacokinetics in humans. Invest. Ophthalmol. Vis. Sci., 37, 1199-1203.
45. Saari, K.M., Nelimarkka, L., Ahola, V., Loftsson, T., Stefánsson, E. (2006). Comparison of topical 0.7% dexamethasone-cyclodextrin with 0.1% dexamethasone sodium phosphate for postcataract inflammation. Graefes Arch. Clin. Exp. Ophthalmol., 244, 620-626.
46. Siefert, B., Keipert, S. (1997). Influence of α-cyclodextrin and hydroxyalkylated β-cyclodextrin derivatives on the in vitro corneal uptake and permeation of aqueous pilocarpine-HCl solutions. J. Pharm. Sci., 86, 716-720.
47. Freedman, K.A., Klein, J.W., Crosson, C.E. (1993). β-Cyclodextrins enhance bioavailability of pilocarpine. Curr. Eye Res., 12, 641-647.
48. Aktas, Y., Ünlu, N., Orhan, M., Irkeç, M., Hincal, A.A. (2003). Influence of hydroxypropyl β-cyclodextrin on the corneal permeation of pilocarpine. Drug Dev. Ind. Pharm., 29, 223-230.
49. Matsubara, K., Abe, K., Irie, T., Uekama, K. (1995). Improvement of nasal bioavailability of luteinizing-hormone-releasing hormone agonist, buserelin, by cyclodextrin derivatives in rats. J. Pharm. Sci., 84, 1295-1300.
50. Shao, Z., Krishnamoorthy, R., Mitra, A.K. (1992). Cyclodextrins as nasal absorption promoters of insulin: mechanistic evaluations. Pharm. Res., 9, 1157-1163.
51. Schipper, N.G.M., Romeijn, S.G., Verhoef, J.C., Merkus, F.W. H.M. (1993). Nasal insulin delivery with dimethyl-β-cyclodextrin as an absorption enhancer in rabbits: powder more effective than liquid formulations. Pharm. Res., 10, 682-686.
52. Zhang, X.N., Xu, J., Tang, L.H., Gong, J., Yan, X.Y., Zhang, Q. (2007). Influence on intestinal mucous permeation of paclitaxel of absorption enhancers and dosage forms based on electron spin resonance spectroscopy. Pharmazie, 62, 368-371.
53. Zheng, Y., Zuo, Z., Chow, A.H.L. (2006). Lack of effect of β-cyclodextrin and its water-soluble derivatives on in vitro drug transport across rat intestinal epithelium. Int. J. Pharm., 309, 123-128.
54. Badawy, S.I.F., Ghorab, M.M., Adeyeye, C.M. (1996). Bioavailability of danazol-hydroxypropyl-β-cyclodextrin complex by different routes of administration. Int. J. Pharm., 145, 137-143.
55. Jain, A.C., Aungst, B.J., Adeyeye, M.C. (2002). Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 β-cyclodextrin (SBE 7) complexes. J. Pharm. Sci., 91, 1659-1668.
56. Rodrigues, J.M., Lima, K.D., Jensen, C.E.D., de Aguiar, M.M. G., Cunha, A.D. (2003). The effect of cyclodextrins on the in vitro and in vivo properties of insulin-loaded poly (D,L-lacticco-glycolic acid) microspheres. Artif. Organs, 27, 492-497.
57. Shao, Z.Z., Li, Y.P., Mitra, A.K. (1994). Cyclodextrins as mucosal absorption promoters of insulin: 3. Pulmonary route of delivery. Eur. J. Pharm. Biopharm., 40, 283-288.
58. Aguiar, M.M.G., Rodrigues, J.M., Cunha, A.S. (2004). Encapsulation of insulin-cyclodextrin complex in PLGA microspheres: a new approach for prolonged pulmonary insulin delivery. J. Microencapsul., 21, 553-564.
59. Hussain, A., Yang, T.Z., Zaghloul, A.A., Ahsan, F. (2003). Pulmonary absorption of insulin mediated by tetradecyl-β-maltoside and dimethyl-β-cyclodextrin. Pharm. Res., 20, 1551-1557.
60. Jalalipour, M., Najafabadi, A.R., Gilani, K., Esmaily, H., Tajerzadeh, H. (2008). Effect of dimethyl-β-cyclodextrin concentrations on the pulmonary delivery of recombinant human growth hormone dry powder in rats. J. Pharm. Sci., 97, 5176-5185.
61. Kobayashi, S., Kondo, S., Juni, K. (1996). Pulmonary delivery of salmon calcitonin dry powders containing absorption enhancers in rats. Pharm. Res., 13, 80-83.
62. Sigurdsson, H.H., Stefánsson, E., Gudmundsdóttir, E., Eysteinsson, T., Thorsteinsdóttir, M., Loftsson, T. (2005). Cyclodextrin formulation of dorzolamide and its distribution in the eye after topical administration. J. Controll. Release, 102, 255-262.
63. Loftsson, T., Hreinsdóttir, D., Stefánsson, E. (2007). Cyclodextrin microparticles for drug delivery to the posterior segment of the eye: aqueous dexamethasone eye drops. J. Pharm. Pharmacol., 59, 629-635.
64. Yang, T., Hussain, A., Paulson, J., Abbruscato, T.J., Ahsan, F. (2004). Cyclodextrins in nasal delivery of low-molecularweight heparins: in vivo and in vitro studies. Pharm. Res., 21, 1127-1136.
65. Loftsson, T., Frithriksdóttir, H., Thorisdóttir, 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.
66. Loftsson, T., Sigurdsson, H.H., Hreinsdóttir, D., Konradsdóttir, F., Stefánsson, E. (2007). Dexamethasone delivery to posterior segment of the eye. J. Inclusion Phenom. Macrocyclic Chem., 57, 585-589.
67. Behl, C.R., Pimplaskar, H.K., Sileno, A.P., deMeireles, J., Romeo, V.D. (1998). Effects of physicochemical properties and other factors on systemic nasal drug delivery. Adv. Drug Deliv. Rev., 29, 89-116.
68. Schipper, N.G.M., Verhoef, J.C., Romeijn, S.G., Merkus, F.W. H.M. (1995). Methylated β-cyclodextrins are able to improve the nasal absorption of salmon-calcitonin. Calcif. Tissue Int., 56, 280-282.
69. Merkus, F.W.H.M., Verhoef, J.C., Romeijn, S.G., Schipper, N. G.M. (1991). Absorption enhancing effect of cyclodextrins on intranasally administered insulin in rats. Pharm. Res., 8, 588-592.
70. Hermens, W.A.J.J., Deurloo, M.J.M., Romeyn, S.G., Verhoef, J.C., Merkus, F.W.H.M. (1990). Nasal absorption enhancement of 17-β-estradiol by dimethyl-β-cyclodextrin in rabbits and rats. Pharm. Res., 7, 500-503.
71. Schipper, N.G.M., Hermens, W.A.J.J., Romeyn, S.G., Verhoef, J., Merkus, F.W.H.M. (1990). Nasal absorption of 17-β-estradiol and progesterone from a dimethyl-cyclodextrin inclusion formulation in rats. Int. J. Pharm., 64, 61-66.
72. Ventura, C.A., Giannone, I., Musumeci, T., Pignatello, R., Ragni, L., Landolfi, C., Milanese, C., Paolino, D., Puglisi, G. (2006). Physico-chemical characterization of disoxaril-dimethyl-β-cyclodextrin inclusion complex and in vitro permeation studies. Eur. J. Med. Chem., 41, 233-240.
73. Merkus, F.W., Verhoef, J.C., Romeijn, S.G., Schipper, N.G. (1991). Absorption enhancing effect of cyclodextrins on intranasally administered insulin in rats. Pharm. Res., 8, 588-592.
74. Vermehren, C., Hansen, H.S., Thomsen, M.K. (1996). Time dependent effects of two absorption enhancers on the nasal absorption of growth hormone in rabbits. Int. J. Pharm., 128, 239-250.
75. Loftsson, T., Gudmundsdóttir, H., Sigurjónsdóttir, J.F., Sigurdsson, H.H., Sigfusson, S.D., Másson, M., Stefánsson, E. (2001). Cyclodextrin solubilization of benzodiazepines: formulation of midazolam nasal spray. Int. J. Pharm., 212, 29-40.
76. Larhed, A.W., Artursson, P., Bjork, E. (1998). The influence of intestinal mucus components on the diffusion of drugs. Pharm. Res., 15, 66-71.
77. Woodcock, B.G., Acerbi, D., Merz, P.G., Rietbrock, S., Rietbrock, N. (1993). Supermolecular inclusion of piroxicam with β-cyclodextrin: pharmacokinetic properties in man. Eur. J. Rheumatol. Inflamm., 12, 12-28.
78. Kimura, E., Bersani-Amado, C.A., Sudo, L.S., Santos, S.R., Oga, S. (1997). Pharmacokinetic profile of piroxicam β-cyclodextrin, in rat plasma and lymph. Gen. Pharmacol., 28, 695-698.
79. Deroubaix, X., Stockis, A., Allemon, A.M., Lebacq, E., Acerbi, D., Ventura, P. (1995). Oral bioavailability of CHF1194, an inclusion complex of piroxicam and β-cyclodextrin, in healthy subjects under single dose and steady-state conditions. Eur. J. Clin. Pharmacol., 47, 531-536.
80. McEwen, J. (2000). Clinical pharmacology of piroxicam-β-cyclodextrin: implications for innovative patient care. Clin. Drug Invest., 19, 27-31.
81. Castillo, J.A., Palomo-Canales, J., García, J.J., Lastres, J.L., Bolas, F., Torrado, J.J. (1999). Preparation and characterization of albendazole β-cyclodextrin complexes. Drug Dev. Ind. Pharm., 25, 1241-1248.
82. El-Gindy, G.A., Mohammed, F.A., Salem, S.Y. (2002). Preparation, pharmacokinetic and pharmacodynamic evaluation of carbamazepine inclusion complexes with cyclodextrins. STP Pharma Sci., 12, 369-378.
83. Brewster, M.E., Anderson, W.R., Meinsma, D., Moreno, D., Webb, A.I., Pablo, L., Estes, K.S., Derendorf, H., Bodor, N., Sawchuk, R., Cheung, B., Pop, E. (1997). Intravenous and oral pharmacokinetic evaluation of a 2-hydroxypropyl-β-cyclodextrin-based formulation of carbamazepine in the dog: comparison with commercially available tablets and suspensions. J. Pharm. Sci., 86, 335-339.
84. Betlach, C.J., Gonzalez, M.A., McKiernan, B.C., Neffdavis, C., Bodor, N. (1993). Oral pharmacokinetics of carbamazepine in dogs from commercial tablets and a cyclodextrin complex. J. Pharm. Sci., 82, 1058-1060.
85. Choudhury, S., Nelson, K.F. (1992). Improvement of oral bioavailability of carbamazepine by inclusion in 2-hydroxypropyl-β-cyclodextrin. Int. J. Pharm., 85, 175-180.
86. Koester, L.S., Ortega, G.G., Mayorga, P., Bassani, V.L. (2004). Mathematical evaluation of in vitro release profiles of hydroxypropylmethylcellulose matrix tablets containing carbamazepine associated to β-cyclodextrin. Eur. J. Pharm. Biopharm., 58, 177-179.
87. Prabagar, B., Yoo, B.K., Woo, J.S., Kim, J.A., Rhee, J.D., Piao, M.G., Choi, H.G., Yong, C.S. (2007). Enhanced bioavailability of poorly water-soluble clotrimazole by inclusion with β-cyclodextrin. Arch. Pharm. Res., 30, 249-254.
88. Uekama, K., Fujinaga, T., Hirayama, F., Otagiri, M., Yamasaki, M., Seo, H., Hashimoto, T., Tsuruoka, M. (1983). Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J. Pharm. Sci., 72, 1338-1341.
89. Savolainen, J., Järvinen, K., Taipale, H., Jarho, P., Loftsson, T., Järvinen, T. (1998). Co-administration of a water-soluble polymer increases the usefulness of cyclodextrins in solid oral dosage forms. Pharm. Res., 15, 1696-1701.
90. Babu, R.J., Pandit, J.K. (1995). Enhancement of dissolution rate and hypoglycemic activity of glibenclamide with β-cyclodextrin. STP Pharma Sci., 5, 196-201.
91. Tenjarla, S., Puranajoti, P., Kasina, R., Mandal, T. (1998). Preparation, characterization, and evaluation of miconazole-cyclodextrin complexes for improved oral and topical delivery. J. Pharm. Sci., 87, 425-429.
92. Barillaro, V., Evrard, B., Delattre, L., Piell, G. (2005). Oral bioavailability in pigs of a miconazole/hydroxypropyl-γ-cyclodextrin/L-tartaric acid inclusion complex produced by supercritical carbon dioxide processing. AAPS J., 7, E149-E155.
93. Soliman, O.A.E., Kimura, K., Hirayama, F., Uekama, K., El Sabbagh, H.M., Abd El Gawad, A.H., Hashim, F.M. (1997). Amorphous spironolactone-hydroxypropylated cyclodextrin complexes with superior dissolution and oral bioavailability. Int. J. Pharm., 149, 73-83.
94. Kaukonen, A.M., Lennernas, H., Mannermaa, J.P. (1998). Water-soluble β-cyclodextrins in paediatric oral solutions of spironolactone: preclinical evaluation of spironolactone bioavailability from solutions of β-cyclodextrin derivatives in rats. J. Pharm. Pharmacol., 50, 611-619.
95. Seo, H., Tsuruoka, M., Hashimoto, T., Fujinaga, T., Otagiri, M., Uekama, K. (1983). Enhancement of oral bioavailability of spironolactone by β-cyclodextrin and γ-cyclodextrin complexations. Chem. Pharm. Bull., 31, 286-291.
96. Savolainen, J., Järvinen, K., Matilainen, L., Järvinen, T. (1998). Improved dissolution and bioavailability of phenytoin by sulfobutylether-β-cyclodextrin ((SBE)(7m)-β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) complexation. Int. J. Pharm., 165, 69-78.
97. Uekama, K., Otagiri, M., Irie, T., Seo, H., Tsuruoka, M. (1985). Improvement of dissolution and absorption characteristics of phenytoin by a water-soluble β-cyclodextrin-epichlorohydrin polymer. Int. J. Pharm., 23, 35-42.
98. Tanino, T., Ogiso, T., Iwaki, M. (1999). Effect of sugarmodified β-cyclodextrins on dissolution and absorption characteristics of phenytoin. Biol. Pharm. Bull., 22, 298-304.
99. Veiga, F., Fernandes, C., Teixeira, F. (2000). Oral bioavailability and hypoglycaemic activity of tolbutamide/cyclodextrin inclusion complexes. Int. J. Pharm., 202, 165-171.
100. Kimura, K., Hirayama, F., Arima, H., Uekama, K. (2000). Effects of aging on crystallization, dissolution and absorption characteristics of amorphous tolbutamide-2-hydroxypropyl-β-cyclodextrin complex. Chem. Pharm. Bull., 48, 646-650.
101. Uekama, K., Horiuchi, Y., Kikuchi, M., Hirayama, F., Ijitsu, T., Ueno, M. (1988). Enhanced dissolution and oral bioavailability of α-tocopheryl esters by dimethyl-β-cyclodextrin complexation. J. Inclusion Phenom., 6, 167-174.
102. Ribeiro, L.S.S., Falcão, A.C., Patricio, J.A.B., Ferreira, D.C., Veiga, F.J.B. (2007). Cyclodextrin multicomponent complexation and controlled release delivery strategies to optimize the oral bioavailability of vinpocetine. J. Pharm. Sci., 96, 2018-2028.
103. Luengo, J., Aranguiz, T., Sepulveda, J., Hernandez, L., Von Plessing, C. (2002). Preliminary pharmacokinetic study of different preparations of acyclovir with β-cyclodextrin. J. Pharm. Sci., 91, 2593-2598.
104. Le Corre, P., Dollo, G., Chevanne, F., Le Verge, R. (1998). Influence of hydroxypropyl-β-cyclodextrin and dimethyl-β-cyclodextrin on diphenhydramine intestinal absorption in a rat in situ model. Int. J. Pharm., 169, 221-228.
105. Miyake, K., Arima, H., Irie, T., Hirayama, F., Uekama, K. (1999). Enhanced absorption of cyclosporin A by complexation with dimethyl-β-cyclodextrin in bile ductcannulated and-noncannulated rats. Biol. Pharm. Bull., 22, 66-72.
106. Singh, B., Ahuja, N. (2002). Development of controlledrelease buccoadhesive hydrophilic matrices of diltiazem hydrochloride: optimization of bioadhesion, dissolution, and diffusion parameters. Drug Dev. Ind. Pharm., 28, 431-442.
107. Rathbone, M.J. (1991). Human buccal absorption: 1. A method for estimating the transfer kinetics of drugs across the human buccal membrane. Int. J. Pharm., 69, 103-108.
108. Cassidy, J.P., Landzert, N.M., Quadros, E. (1993). Controlled buccal delivery of buprenorphine. J. Controll. Release, 25, 21-29.
109. Guo, J.H. (1994). Bioadhesive polymer buccal patches for buprenorphine controlled delivery: formulation, in-vitro adhesion and release properties. Drug Dev. Ind. Pharm., 20, 2809-2821.
110. Han, R.Y., Fang, J.Y., Sung, K.C., Hu, O.Y.P. (1999). Mucoadhesive buccal disks for novel nalbuphine prodrug controlled delivery: effect of formulation variables on drug release and mucoadhesive performance. Int. J. Pharm., 177, 201-209.
111. Boulmedarat, L., Bochot, A., Lesieur, S., Fattal, E. (2005). Evaluation of buccal methyl-β-cyclodextrin toxicity on human oral epithelial cell culture model. J. Pharm. Sci., 94, 1300-1309.
112. Pinto, J.M.C.L., Marques, H.M.C. (1999). Beclomethasone/cyclodextrin inclusion complex for dry powder inhalation. STP Pharma Sci., 9, 253-256.