Use of cyclodextrins in topical formulations: Practical aspects

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 68, Issue 3, 2008, Pages 467-478

  Cal, Krzysztof ^a   Centkowska, Katarzyna ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Cyclodextrins; Mucosal delivery; Ocular delivery; Skin penetration; Topical preparations; Toxicity

Indexed keywords

2,6 DIMETHYL BETA CYCLODEXTRIN; ACETAZOLAMIDE; ALFADEX; ALPHA CYCLODEXTRIN; ALPHA CYCLODEXTRIN DERIVATIVE; BENZAMIDE DERIVATIVE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CELECOXIB; CHLORAMPHENICOL; CLOROCIL; CYCLODEXTRIN; DICLOFENAC; DIMEB 50; DIMEB 80; DIMEB 95; DIMETHYL BETA CYCLODEXTRIN; DISOXARIL; DISULFIRAM; DORZOLAMIDE; EYE DROPS; GAMMA CYCLODEXTRIN; GAMMA CYCLODEXTRIN DERIVATIVE; GANCICLOVIR; HYDROCORTISONE; INDOCOLYRE; INDOMETACIN; ITRACONAZOLE; LIPOSOME; METHAZOLAMIDE; N,N DIETHYL 3 METHYLBENZAMIDE; PIROXICAM BETA CYCLODEXTRIN; RETINOIC ACID; SUNSCREEN; TROPICAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BIOEQUIVALENCE; CILIARY MOTILITY; CORNEA; CYTOTOXICITY; DESQUAMATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG FORMULATION; DRUG INDUSTRY; DRUG PENETRATION; DRUG RELEASE; DRUG STABILITY; DRUG STRUCTURE; DRUG UPTAKE; ERYTHEMA; EYE IRRITATION; EYE TOXICITY; HUMAN; HYDROPHOBICITY; LEGAL ASPECT; NONHUMAN; NOSE MUCOSA; PHYSICAL CHEMISTRY; REVIEW; SIDE EFFECT; SKIN PERMEABILITY; SKIN TOXICITY; STOICHIOMETRY; XEROSIS;

EID: 39849095718     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2007.08.002     Document Type: Review

References (123)

1. T. Loftsson M.E. Brewster Pharmaceutical applications of cyclodextrins. I. Drug solubilization and stabilization J. Pharm. Sci. 85 1996 1017 1025
2. R.C. Rowe P.J. Sheskey P.J. Weller Handbook of Pharmaceutical Excipients 4th ed. 2003 Pharmaceutical Press London, Chicago 186 189
3. K.H. Fromming J. Szejtli Topics in Inclusion Science Cyclodextrins in Pharmacy vol. 5 1994 Kluwer Academic Publishers Dortrecht, Boston, London
4. M.H. Rubinstein Pharmaceutical Technology Drug Stability 1989 Ellis Horwood Ltd, John Wiley and Sons New York, Chichester, Brisbane, Toronto 9 22
5. E.M.M. Del Valle Cyclodextrins and their uses: a review Process Biochem. 39 2004 1033 1046
6. H. Matsuda H. Arima Cyclodextrins in transdermal and rectal delivery Adv. Drug Deliv. Rev. 36 1999 81 99
7. P.S. Martins R. Ochoa A.M.C. Pimenta L.A.M. Ferreira A.L. Melo J.B.B. da Silva R.D. Sinisterra C. Demicheli F. Frezard Mode of action of β-cyclodextrin as an absorption enhancer of the water-soluble drug meglumine antimoniate Int. J. Pharm. 325 2006 39 47
8. T. Loftsson M. Masson M.E. Brewster Self-association of cyclodextrins and cyclodextrin complexes J. Pharm. Sci. 93 2004 1091 1099
9. M.S. Duan N. Zhao I.B. Ossurardottir T. Thorsteinsson T. Loftsson Cyclodextrins solubilization of the antibacterial agents triclosan and triclocarban: formation of aggregates and higher-order complexes Int. J. Pharm. 297 2005 213 222
10. T. Loftsson K. Matthiasson M. Masson The effects of organic salts on the cyclodextrin solubilization of drugs Int. J. Pharm. 262 2003 101 107
11. V.J. Stella V.M. Rao E.A. Zannou V. Zia Mechanisms of drug release from cyclodextrin complexes Adv. Drug Deliv. Rev. 36 1999 3 16
12. T. Loftsson M. Masson Cyclodextrins in topical drug formulations: theory and practice Int. J. Pharm. 225 2001 15 30
13. T. Loftsson S.D. Sigfusson H.H. Sigurdsson M. Masson The effects of cyclodextrins on topical delivery of hydrocortisone: the aqueous diffusion layer STP Pharma Sci. 13 2003 125 131
14. C.A. Ventura I. Giannone T. Musumeci R. Pignatello L. Ragini C. Landolfi C. Milanese D. Paolino G. Puglisi Physico-chemical characterization of disoxaril-dimethyl-β-cyclodextrin inclusion complex and in vitro permeation studies Eur. J. Med. Chem. 41 2006 233 240
15. A. Doliwa S. Santoyo P. Ygartua Influence of piroxicam: hydroxypropyl-beta-cyclodextrin complexation on the in vitro permeation and skin retention of piroxicam Skin Pharmacol. Appl. Skin. Physiol. 14 2001 97 107
16. S.N. Murthy Y.L. Zhao A. Sen S.W. Hui Cyclodextrin enhanced transdermal delivery of piroxicam and carboxyfluorescein by electroporation J. Control. Release 99 2004 393 402
17. R.A. Rajewski V.J. Stella Pharmaceutical application of cyclodextrins. II. In vivo drug delivery J. Pharm. Sci. 85 1996 1142 1169
18. T. Irie K. Uekama Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation J. Pharm. Sci. 84 1997 147 162
19. T. Jansen B. Xhonneux J. Mesens M. Borgers Beta-cyclodextrins as vehicles in eye-drop formulations: an evaluation of their effects on rabbit corneal epithelium Lens Eye Toxic. Res. 7 1990 459 468
20. P. Saarinen-Savolainen T. Jarvinen K. Araki-Sasaki H. Watanabe A. Urtti Evaluation of citotoxicity of various ophtalmic drugs, eye drop excipients and cyclodextrins in an immortalized human corneal epithelial cell line Pharm. Res. 15 1998 1275 1280
21. L. Boulmedarat A. Bochot S. Lesieur E. Fattal Evaluation of buccal methyl-β-cyclodextrin toxicity on human oral epithelial cell culture model J. Pharm. Sci. 94 2005 1300 1309
22. K. Uekama Design and evaluation of cyclodextrins-based drug formulation Chem. Pharm. Bull. 52 2004 900 915
23. J. Szejtli Cyclodextrin complexed generic drugs are generally not bio-equivalent with the reference products: therefore the increase in number of marketed drug/cyclodextrin formulations is so slow J. Incl. Phenom. Macrocycl. Chem. 52 2005 1 11
24. Y. Ohtani T. Irie K. Uekama K. Fukunaga J. Pitha Differential effects of α-, β- and γ-cyclodextrins on human erythrocytes Eur. J. Biochem. 186 1989 17 22
25. J.C. Debouzy F. Fauvelle S. Crouzy L. Girault Y. Chapron M. Goschl A. Gadelle Mechanism of α-cyclodextrin induced hemolysis. 2. A study of the factors controlling the association with serine-, ethanolamine-, and choline-phospholipids J. Pharm. Sci. 87 1998 59 66
26. K. Motoyama H. Arima H. Toyodome T. Irie F. Hirayama K. Uekama Effect of 2,6-di-0-methyl-α-cyclodextrin on hemolysis and morphological change in rabbit’s red blood cells Eur. J. Pharm. Sci. 29 2006 111 119
27. K. Asai M. Morishita H. Katsuta S. Hosoda K. Shinomiya M. Noro T. Nagai K. Takayama The effects of water-soluble cyclodextrins on the histological integrity of the rat nasal mucosa Int. J. Pharm. 246 2002 25 35
28. R.U. Agu M. Jorissen T. Willems G. Van den Mooter R. Kinget N. Verbeke P. Augustijns Safety assessment of selected cyclodextrins – effect on ciliary activity using a human cell suspension culture model exhibiting in vitro ciliogenesis Int. J. Pharm. 193 2000 219 226
29. S.G. Romeijn J.C. Verhoef E. Marttin F.W.H.M. Merkus The effect of nasal drug formulations on ciliary beating in vitro Int. J. Pharm. 135 1996 137 145
30. W.M. Boek S.G. Romeijn K. Graamans J.C. Verhoef F.W.H.M. Merkus E.H. Huizing Validation of animal experiments on ciliary function in vitro. II. The influence of absorption enhancers, preservatives and physiologic saline Acta Otolaryngol. 119 1999 98 101
31. G. Piel S. Moutard E. Uhoda F. Pilard G.E. Pierard B. Perly L. Delattre B. Evrard Skin compatibility of cyclodextrins and their derivatives: a comparative assessment using a corneoxenometry bioassay Eur. J. Pharm. Biopharm. 57 2004 479 482
32. D.S. Shaker A.H. Ghanem S.K. Li K.S. Warner F.M. Hashem W.I. Higuchi Mechanistic studies of the effect of hydroxypropyl-β-cyclodextrin on in vitro transdermal permeation of corticosterone through hairless mouse skin Int. J. Pharm. 253 2003 1 11
33. J.Y. Legendre I. Rault A. Petit W. Luijten I. Demuynck S. Horvath Y.M. Ginot A. Cuine Effects of β-cyclodextrins on skin: implications for the transdermal delivery of piribedil and a novel cognition enhancing-drug S-9977 Eur. J. Pharm. Sci. 3 1995 311 322
34. S. Gould R.C. Scott 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): a toxicology review Food Chem. Toxicol. 43 2005 1451 1459
35. D.H. Waalkens-Berendsen A. Bar Embriotoxicity and teratogenity study with α-cyclodextrin in rats Regul. Toxicol. Pharmacol. 39 2004 34 39
36. I.C. Munro P.M. Newberne V.R. Young A. Bar Safety assessment of γ-cyclodextrin Regul. Toxicol. Pharmacol. 39 2004 3 13
37. R. Challa A. Ahuja J. Ali R.K. Khar Cyclodextrins in drug delivery: an updated review AAPS Pharm. Sci. Tech. 6 2005 article 43 ( www.aapspharmscitech ).
38. M. Shigeyama T. Ohgaya Y. Kawashima H. Takeuchi T. Hino Modification of the physicochemical properties of minocycline hydrochloride ointment with cyclodextrines for optimum treatment of bedsore Chem. Pharm. Bull. 48 2000 617 622
39. S. Proniuk J. Blanchard Influence of degree of substitution of cyclodextrins on their colligative properties in solution J. Pharm. Sci. 90 2001 1086 1090
40. M.E. Davis M.E. Brewster Cyclodextrin-based pharmaceutics: past, present and future Nat. Rev. Drug Discov. 3 2004 1023 1035
41. J. Blanchard S. Proniuk Some important considerations in the use of cyclodextrins Pharm. Res. 16 1999 1796 1798
42. Guideline on excipients in the dossier for application for marketing authorisation of a medicinal product (draft), Doc. Ref. EMEA/CHMP/QWP/396951/2006, EMEA, London, 2006.
43. D.A. Godwin C.J. Wiley L.A. Felton Using cyclodextrin complexation to enhance secondary photoprotection of topically applied ibuprofen Eur. J. Pharm. Biopharm. 62 2006 85 93
44. R.Y. Anadolu T. Sen N. Tarimici A. Birol C. Erdem Improved efficacy and tolerability of retinoic acid in acne vulgaris: a new topical formulation with cyclodextrin complex ψ J. Eur. Acad. Dermatol. Venerol. 18 2004 1 6
45. T. Rode M. Frauen B.W. Muller H.J. Dusing U. Schonrock C. Mundt H. Wenck Complex formation of sericoside with hydrophilic cyclodextrins: improvement of solubility and skin penetration in topical emulsion based formulations Eur. J. Pharm. Biopharm. 55 2003 191 198
46. R.F.V. Lopez J.H. Collet M. Vitoria L.B. Bentley Influence of cyclodextrin complexation on the in vitro permeation and skin metabolism of dexamethasone Int. J. Pharm. 200 2000 127 132
47. S. Sirdevei P.V. Rao Diwan Optimized transdermal delivery of ketoprofen using pH and hydroxypropyl-β-cyclodextrin as co-enhancers Eur. J. Pharm. Biopharm. 54 2002 151 154
48. E. Bilensoy M.A. Rouf I. Vural M. Sen A.A. Hincal Mucoadhesive, thermosensitive, prolonged-release vaginal gel for clotrimazole: β-cyclodextrin complex AAPS Pharm. Sci. Tech. 7 2006 article 38 ( www.aapspharmscitech ).
49. S. Proniuk B.M. Liederer S.E. Dixon J.A. Rein M.A. Kallen J. Blanchard Topical formulation studies with DEET ( N , N -diethyl-3-methylbenzamide) and cyclodextrins J. Pharm. Sci. 91 2002 101 110
50. S. Scalia R. Tursilli N. Sala V. Iannuccelli Encapsulation in liposphers of the complex between butyl methoxydibenzoylmethane and hydroxypropyl-β-cyclodextrin Int. J. Pharm. 320 2006 79 85
51. G.L. Flynn V.P. Shah S.N. Tenjarla M. Corbo D. DeMagistris T.G. Feldman T.J. Franz D.R. Miran D.M. Pearce J.A. Sequeira J. Swarbrick J.C.T. Wang A. Yacobi J.L. Zatz Assessment of value and applications on in vitro testing of topical dermatological drug products Pharm. Res. 16 1999 1325 1330
52. M. Jug M. Becirevic-Lacan A. Kwokal B. Cetina-Cizmek Influence of cyclodextrin complexation on piroxicam gel formulations Acta Pharm. 55 2005 223 236
53. F. Maestrelli M.L. Gonzalez-Rodríguez A. Rabasco P. Mura Effect of preparation technique on the properties of liposomes encapsulating ketoprofen-cyclodextrin complexes aimed for transdermal delivery Int. J. Pharm. 312 2006 53 60
54. H.H. Sigurdsson E. Stefansson E. Gudmundsdottir T. Eysteinsson M. Thorsteinsdottir T. Loftsson Cyclodextrin formulation of dorzolamide and its distribution in the eye after topical administration J. Control Release 102 2005 255 262
55. B. Cappello C. Carmignani M. Iervolino M.I. La Rotonda M.F. Saettone Solubilization of tropicamide by hydroxypropyl-β-cyclodextrin and water-soluble polymers: in vitro/in vivo studies Int. J. Pharm. 213 2001 75 81
56. A.R. Bary I.G. Tucker N.M. Davies Consideration in the use of hydroxypropyl-β-cyclodextrin in the formulation of aqueous ophthalmic solutions of hydrocortisone Eur. J. Pharm. Biopharm. 50 2000 237 244
57. S. Burgalassi P. Chetoni D. Monti M.F. Saettone Cytotoxicity of potential ocular permeation enhancers evaluated on rabbit and human corneal epithelial cell lines Toxicol. Lett. 122 2001 1 8
58. R.G. Alany T. Rades J. Nicoll I.G. Tucker N.M. Davies W/O micro emulsion for ocular delivery: Evaluation of ocular irritation and precorneal retention J. Control Release 111 2006 145 152
59. P. Furrer B. Plazonnet J.M. Mayer R. Gurny Application of in vivo confoal microscopy to the objective evaluation of ocular irritation induced by surfactants Int. J. Pharm. 207 2000 89 98
60. P. Montassier D. Duchen M.C. Poe lman In vitro release study of tretinoin from tretinoin/cyclodextrin derivative complexes J. Incl. Phenom. Molec. Recogn. Chem. 31 1998 213 218
61. P. Montassier D. Duchen M.C. Poelman Inclusion complexes of tretinoin with cyclodextrin Int. J. Pharm. 153 1997 199 209
62. C.A. Ventura S. Tommasini A. Falcone I. Giannone D. Paolino V. Sdrafkakis M.R. Mondello G. Puglisi Influence of modified cyclodextrins on solubility and percutaneous absorption of celecoxib through human skin Int. J. Pharm. 314 2006 37 45
63. I.P. Kaur R. Smitha D. Aggarwal M. Kapil Acetazolamide: future perspective in topical glaucoma therapeutics Int. J. Pharm. 248 2002 1 14
64. E. Guomundsdottir E. Stefansson G. Bjarnadottir J.F. Sigurjonsdottir G. Guomundsdottir M. Masson T. Loftsson Methazolamide 1% in cyclodextrin solution lowers IOP in human ocular hypertension Invest. Ophtalmol. Vis. Sci. 41 2002 3522 3554
65. B. Siefert U. Pleyer M. Mulle S. Keipert C. Hartmann Influence of cyclodextrins on the in vitro corneal permeability and in vivo ocular distribution of thialidomide J. Ocul. Pharmacol. Ther. 15 1999 429 438
66. G.S. Tirucherai A.K. Mitra Effect on hydroxypropyl-beta-cyclodextrin complexation on aqueous solubility, stability, and corneal permeation of acyl ester prodrugs of ganciclovir AAPS Pharm. Sci. Tech. 4 2003 article 45 ( www.aapspharmscitech ).
67. S. Wang D. Li Y. Ito T. Nabekura S. Wang J. Zhang C. Wu Bioavailability and anticataract effects of a topical ocular drug delivery system containing disulfiram and hydroxypropyl-beta-cyclodextrin on selenite treated rats Curr. Eye Res. 29 2004 51 58
68. S. Wang D. Li Y. Ito X. Liu J. Zhang C. Wu An ocular drug delivery system containing zinc diethyldithiocarbamate and HP-β-CD inclusion complex – corneal permeability, anti-cataract effects and mechanism studies J. Pharm. Pharmacol. 56 2004 1251 1257
69. J. Jutunen T. Jarvinem R. Niemi In-vitro permeation of cannabinoids and their water-soluble phosphate ester prodrugs J. Pharm. Pharmacol. 57 2005 1153 1157
70. S. Knapp E. Bertelmann C. Hartmann S. Keipert U. Pleyer Intraocular availability of topically applied mycophenolate mofetil in rabbits J. Ocul. Pharmacol. Ther. 19 2003 181 192
71. H. Arima T. Miyaji T. Irie F. Hirayama K. Uekama Possible enhancing mechanism of the cutaneous permeation of 4-biphenylylacetic acid by β-cyclodextrin derivatives in hydrophilic ointment Chem. Pharm. Bull. 44 1996 582 586
72. A.M. Siguroardottir T. Loftsson The effect of polyvinylpyrrolidone on cyclodextrin complexation of hydrocortisone and its diffusion through hairless mouse skin Int. J. Pharm. 126 1995 73 78
73. L. Felton C.J. Wiley D.A. Godwin Influence of hydroxypropyl-β-cyclodextrin on the transdermal permeation and skin accumulation of oxybenzone Drug Dev. Ind. Pharm. 28 2002 1117 1124
74. R.J. Babu J.K. Pandit Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin Int. J. Pharm. 271 2004 155 165
75. C. Schoch J.C. Bizec G. Kis Cyclodextrin derivatives and cyclofructan as ocular permeation enhancers: results with different model compounds J. Incl. Phenom. Macrocycl. Chem. 57 2007 391 394
76. D. Passali R. Balli A. Scotti V. Oldani Controlled, double-blind randomized comparison of nimesulide β-cyclodextrin and morniflumate in acute otitis Curr. Ther. Res. 62 2001 153 166
77. K.M. Saari L. Nelimarkka V. Ahola T. Loftsson E. Stefansson Comparison of topical 0.7% dexamethasone-cyclodextrin with 0. 1% dexomethasone sodium phosphate for postcataract inflammation Graefes Arch. Clin. Exp. Ophthalmol. 244 2006 620 626
78. S. Davaran M.R. Rashidi R. Khandaghi M. Hashemi Development of a novel prolonged-release nicotine transdermal patch Pharm. Res. 51 2005 233 237
79. B. Pose-Vilarnovo C. Rodriguez-Tenreiro J.F. Rosa dos Santos J. Vazquez-Doval A. Concheiro C. Alvarez-Lorenzo J.J. Torres-Labandeira Modulating drug release with cyclodextrins in hydroxypropyl methylcellulose gels and tablets J. Control Release 94 2004 351 363
80. E.Y. Kim Z.G. Gao J.S. Park H. Li K. Han rhEGF/HP-β-CD complex in poloxamer gel for ophthalmic delivery Int. J. Pharm. 233 2002 159 167
81. S. Scalia A. Casolari A. Iaconinoto S. Simeoni Comparative studies of the influence of cyclodextrins on the stability of the sunscreen agent, 2-ethylhexyl-p-methoxycinnamate J. Pharm. Biomed. Anal. 30 2002 1181 1189
82. S. Scalia A. Molinari A. Casolari A. Maldotti Complexation of the sunscreen agent, phenylbenzimidazole sulphonic acid with cyclodextrins: effect on stability and photo-induced free radical formation Eur. J. Pharm. Sci. 22 2004 241 249
83. T. Loftsson H. Gudmundsdottir J.F. Sigurjonsdottir H.H. Sigurdsson S.D. Sigfusson M. Masson E. Stefansson Cyclodextrin solubilization of benzodiazepines: formulation of midazolam nasal spray Int. J. Pharm. 212 2001 29 40
84. M. Francois E. Snoeckx P. Putteman F. Wouters E. De Proost U. Delaet J. Peeters M.E. Brewster A mucoadhesive, cyclodextrin-based vaginal cream formulation of itraconazole AAPS Pharm. Sci. Tech. 5 2003 article 5 ( www.aapspharmscitech ).
85. V.J. Stella R.A. Rajewski Cyclodextrins: their future in drug formulation and delivery Pharm. Res. 14 1997 556 567
86. T. Loftsson E. Stefansson Effect of cyclodextrins on topical drug delivery to the eye Drug Dev. Ind. Pharm. 23 1997 473 481
87. T. Loftsson B.J. Olaftsdottir N. Bodor The effects of cyclodextrins on transdermal delivery of drugs Eur. J. Pharm. Biopharm. 37 1991 30 33
88. T. Loftsson E. Marcus E. Brewster M. Mason Role of cyclodextrins in improving oral drug delivery Am. J. Drug Deliv. 2 4 2004
89. S.J. Lehner B.W. Muller J.K. Seydel Interaction between p -hydroxybenzoic acid esters and hydroxyproyl-β-cyclodextrin and their antimicrobial effect against Candida Albicans Int. J. Pharm. 93 1993 201 208
90. S.J. Lehner B.W. Muller J.K. Seydel Effect of hydroxyproyl-β-cyclodextrin on the antimicrobial action of preservatives J. Pharm. Pharmacol. 46 1994 186 191
91. L.W. Chan T.R.R. Kurup A. Muthaiah J.C. Thenmozhiyal Interaction of p -hydroxybenzoic esters with beta-cyclodextrin Int. J. Pharm. 195 2000 71 79
92. ® (eye drops) prescribing information, Poland, May 2003.
93. M. Shigeyama Preparation of gel-forming ointment base applicable to the recovery stage of bedsore and clinical evaluation of treatment method with different ointment base suitable to each stage of bedsore Yakugaku Zasshi 124 2004 55 67
94. A. Harada Preparation and structures of supramolecules between cyclodextrins and polymers Coordin. Chem. Rev. 148 1996 115 133
95. L. Boulmedarat J.L. Grossiord E. Fattal A. Bochot Influence of methyl-β-cyclodextrin and liposomes on rheological properties of Carbopol 974P NF gels Int. J. Pharm. 254 2003 59 64
96. U. Vollmer B.W. Muller J. Peeters J. Mesens B. Wiffert T. Peters A study of the percutaneous absorption-enhancing effects of cyclodextrins derivatives in rats J. Pharm. Pharmacol. 46 1994 19 22
97. A.C. Williams Transdermal and Topical Drug Delivery 2003 Pharmaceutical Press London, Chicago
98. M.V.L.B. Bentley R.F. Vianna S. Wilson J.H. Collett Characterization of the influence of some cyclodextrins on the stratum corneum from the hairless mouse J. Pharm. Pharmacol. 49 1997 397 402
99. R. Valjakka-Koskela J. Hirvonen J. Monkkonem J. Kiessvaara S. Antila L. Lehtonen A. Urtti Transdermal delivery of levosimendan Eur. J. Pharm. Sci. 11 2000 343 350
100. A. Preis W. Mehnert K.H. Fromming Penetration of hydrocortisone into excised human skin under the influence of cyclodextrins Pharmazie 50 1995 121 126
101. S. Simeoni S. Scalia H.A.E. Benson Influence of cyclodextrins on in vitro human skin absorption of the sunscreen, butyl-methoxydibenzoylmethane Int. J. Pharm. 280 2004 163 171
102. S. Simeoni S. Scalia R. Tursilli H. Benson Influence of cyclodextrin complexation on the in vitro human skin penetration and retention of the sunscreen agent, oxybenzone J. Incl. Phenom. Macrocycl. Chem. 54 2006 275 282
103. T. Higuchi K.A. Connors Phase-solubility techniques Adv. Anal. Chem. Instrum. 4 1965 117 212
104. Y. Guillaume C. Andre N. Simon A. Gehin C. Guyon M. Thomassin L. Ismaili F. Aubin L. Nicod Chromatographic determination of the association constant between 8-methoxypsoralen and modified β-cyclodextrin: protective effect of hydroxypropyl-β-cyclodextrin on 8-methoxypsoralen toxicity in human keratinocytes J. Chromatogr. B 798 2003 217 222
105. S. Scalia R. Tursilli A. Bianchi P. Lo Nostro E. Bocci F. Ridi P. Baglioni Incorporation of the sunscreen agent, octyl methoxycinnamate in a cellulosic febric grafted with β-cyclodextrin Int. J. Pharm. 308 2006 155 159
106. N. Skalko-Basnet Z. Pavelic M. Becirevic-Lacan Liposomes containing drug and cyclodextrin prepared by the one-step spray-drying method Drug Dev. Ind. Pharm. 26 2000 1279 1284
107. L. Boulmedarat G. Piel A. Bochot S. Lesieur L. Delattre E. Fattal Cyclodextrin-mediated drug release from liposomes dispersed within a bioadhesive gel Pharm. Res. 22 2005 962 971
108. S. Hartel H.A. Diehl S.F. Ojeda Methyl-β-cyclodextrins and liposomes as water-soluble carriers for cholesterol incorporation into membranes and its evaluation by a microenzymatic fluorescence assay and membrane fluidity-sensitive dyes Anal. Biochem. 258 1998 277 284
109. G. Piel M. Piette V. Barillaro D. Castagne B. Evrard L. Delattre Bethamethasone-in-cyclodextrin-in-liposome: the effect of cyclodextrins on encapsulation efficacy and release kinetics Int. J. Pharm. 312 2006 75 82
110. ®) in allergic rhinitis treatment Biomaterials 25 2004 159 170
111. R.M. Mainardes M.C. Cocenza Urban P.C. Cinto M.V. Chaud R.C. Evangelista M.P. Daflon Gremiao Liposomes and micro/nanoparticles as colloidal carriers for nasal drug delivery Curr. Drug Deliv. 3 2006 275 285
112. M. Jug M. Becirevic-Lacan B. Cetina-Cizmek M. Horvat Hydroxypropyl methylcellulose microspheres with piroxicam and piroxicam-hydroxypropyl-β-cyclodextrin inclusion complex Pharmazie 59 2004 686 691
113. J. Filipovic-Gracic D. Voinovich M. Moneghini M. Becirevic-Lacan L. Magarotto I. Jaslenjak Chitosan microspheres with hydrocortisone and hydrocortisone-hydroxypropyl-β-cyclodextrin inclusion complex J. Pharm. Sci. 9 2000 373 379
114. B. Martel M. Morcellet D. Ruffin F. Vinet M. Weltrowski Capture and controlled release of fragrances by CD finished textiles J. Incl. Phenom. Macrocycl. 44 2002 439 442
115. H.J. Buschmann D. Knittel E. Schollmeyer New textile application of cyclodextrins J. Incl. Phenom. Macrocycl. Chem. 40 2001 169 172
116. A.E. Tornelli The potential for improving medical textiles with cyclodextrins inclusion compounds J. Textile Apparel Technol. Manag. 3 2 2003 ( www.tx.ncsu.edu/jtatm/ ).
117. U. Siemoneit C. Schmitt C. Alvarez-Lorenzo A. Luzardo F. Otero-Espinar A. Concheiro J. Blanco-Méndez Acrylic/cyclodextrin hydrogels with enhanced drug loading and sustained release capability Int. J. Pharm. 312 2006 66 74
118. B. Martel D. Ruffin M. Weltrowski Y. Lekchiri M. Morcellet Water-soluble polymers and gels from the polycondensation between cyclodextrins and poly(carboxylic acid)s: a study of the preparation parameters J. Appl. Polym. Sci. 97 2005 433 442
119. M.M.R. Dias S.L. Raghavan M.A. Pellett J. Hadgraft The effect of β-cyclodextrins on the permeation of diclofenac from supersaturated solutions Int. J. Pharm. 263 2003 173 181
120. A. Doliwa S. Santoyo P. Ygartua Effect of passive and iontophoretic skin pretreatments with terpenes on the in vitro skin transport of piroxicam Int. J. Pharm. 229 2001 37 44
121. T. Yamakawa S. Nishimura Liquid formulation of a novel non-fluorinated topical quinolone, T-3912, utilizing the synergic solubilizing effect of the combined use of magnesium ions and hydroxypropyl-β-cyclodextrin J. Control Release 86 2003 101 113
122. I. Nandi M. Bateson M. Bari H.N. Joshi Synergistic effect of PEG-400 and cyclodextrins to enhance solubility of progesterone AAPS Pharm. Sci. Tech. 4 2003 article 1 ( www.aapspharmscitech )
123. T. Loftsson D. Duchene Cyclodextrins and their pharmaceutical applications Int. J. Pharm. 329 2007 1 11