Influence of aqueous diffusion layer on passive drug diffusion from aqueous cyclodextrin solutions through biological membranes

Pharmazie

Volumn 61, Issue 2, 2006, Pages 83-89

  Loftsson, Thorsteinn ^a   Konradsdottir F ^a   Masson M ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN;

AQUEOUS SOLUTION; CELL MEMBRANE; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DIFFUSION; DRUG PENETRATION; DRUG SOLUBILITY; HUMAN; HYDROPHILICITY; LIPOPHILICITY; NONHUMAN; REVIEW;

ANIMALS; CYCLODEXTRINS; DIFFUSION; HUMANS; MEMBRANES; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; SOLUTIONS; WATER;

EID: 33644555897     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (70)

1. Adachi H, Irie T, Uekama K, Manako T, Yano T, Saita M (1992) Inhibitory effect of prostaglandin E1 on laurate-induced peripheral vascular occlusive sequelae in rabbits; optimized topical formulation with β-cyclodextrin derivative and penetration enhancer HPE-101. J Pharm Pharmacol 44: 1033-1035.
2. Adachi H, Irie T, Uekama K, Manako T, Yano T, Saita M (1993) Combination effects of O-carboxymethyl-O-ethyl-β-cyclodextrin and penetration enhancer HPE-101 on transdermal delivery of prostaglandin-E(1) in hairless mice. Eur J Pharm Sci 1: 117-123.
3. Amdidouche D, Montassier P, Poelman MC, Duchene D (1994) Evaluation by laser-doppler velocimetry of the attenuation of tretioin induced skin irritation by β-cyclodextrin complexation. Int J Pharm 111: 111-116.
4. Amidon GL, Lennernäs H, Shah VP, Crison JR (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.
5. Arima H, Miyaji T, Irie T, Hirayama F, Uekama K (1996) Possible enhancing mechanism of the cutaneous permeation of 4-biphenylylacetic acid by β-cyclodextrin derivatives in hydrophilic ointment. Chem Pharm Bull 44: 582-586.
6. Arima H, Miyaji T, Irie T, Hirayama F, Uekama K (1998) Enhancing effect of hydroxypropyl-β-cyclodextrin on cutaneous penetration activation of ethyl 4-biphenylyl acetate in hairless mouse skin. Eur J Pharm Sci 6: 53-59.
7. Babu RJ, Pandit JK (2004) Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin. Int J Pharm 271: 155-165.
8. Bary AR, Tucker IG, Davies NM (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.
9. Bergeron RJ (1984) Cycloamylose-substrate binding. In: Attwood JL, Bavies JED, MacNicol DD (eds) Cycloamylose-substrate binding Book, Academic Press London, p. 391-443.
10. Chang SL, Banga AK (1998) Transdermal iontophoretic delivery of hydrocortisone from cyclodextrin solutions. J Pharm Pharmacol 50: 635-640.
11. Cho MJ, Chen FJ, Huczek DL (1995) Effects of inclusion complexation on the transepithelial transport of a lipophilic substance in vitro. Pharm Res 12: 560-564.
12. Connors KA (1995) Population characteristics of cyclodextrin complex stabilities in aqueous solution. J Pharm Sci 84: 843-848.
13. Connors KA (1997) The stability of cyclodextrin complexes in solution. Chem Rev 97: 1325-1357.
14. Duan M, Zhao N, Össurardottir ÍB, 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.
15. Felton LA, Wiley CJ, Godwin DA (2002) Influence of hydroxypropyl-β- cyclodextrin on transdermal permeation and skin accumulation of oxybenzone. Drug Devel Ind Pharm 28: 1117-1124.
16. Felton LA, Wiley CJ, Godwin DA (2004) Influence of cyclodextrin complexation on the in vivo photoprotective effects of oxybenzone. Drug Devel Ind Pharm 30: 95-102.
17. Florence AT, Attwood D (1998) Physicochemical principles of pharmacy. 3rd Edition, Macmillan Press, London.
18. Flynn GL, Carpender OS, Yalkowsky SH (1972) Total mathematical resolution of diffusion layer control of barrier flux. J Pharm Sci 61: 312-314.
19. Frömming KH, Szejtli J (1994) Cyclodextrins in pharmacy, Kluwer Academic Publishers, Dordrecht.
20. Gerlóczy A, Antal S, Szejtli J (1988) Percutaneous absorption of heptakis-(2,6-di-O-14C-methyl)-β-cyclodextrin in rats. In: Huber O, Szejtli J (eds) Percutaneous absorption of heptakis-(2,6-di-O-14C-methyl)-β- cyclodextrin in rats Book, Kluwer Academic Publishers, Dordrecht, p. 415-420.
21. González-Gaitano G, Rodríguez P, Isasi JR, Fuentes M, Tardajos G, Sánchez M (2002) The aggregation of cyclodextrins as studied by photon correlation spectroscopy. J Incl Phenom Macrocycl Chem 44: 101-105.
22. 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.
23. Jarho P, Urtti A, Pate DW, 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: 209-217.
24. Kublik H, Bock TK, Schreier H, Müller BW (1996) Nasal absorption of 17β-estradiol from different cyclodextrin inclusion formulations in sheep. Eur J Pharm Biopharm 42: 320-324.
25. Legendre JY, Rault I, Petit A, Luijten W, Demuynck I, Horvath S, Ginot YM, Cuine A (1995) 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: 311-322.
26. Lennernäs H (1998) Human intestinal permeability. J Pharm Sci 87: 403-410.
27. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2001) Experimental and computatorial approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46: 3-26.
28. Liu L, Guo Q-X (2002) The driving forces in the inclusion complexation of cyclodextrins. J Incl Phenom Macroc Chem 42: 1-14.
29. Loftsson T, Brewster ME (1996) Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85: 1017-1025.
30. Loftsson T, Brewster ME, Másson M (2004a) Role of cyclodextrins in improving oral drug delivery. Am J Drug Deliv 2: 261-275.
31. Loftsson T, Jarho P, Másson M, Järvinen T (2005a) Cyclodextrins in drug delivery. Expert Opin Drug Deliv 2: 335-351.
32. Loftsson T, Järvinen T (1999) Cyclodextrins in ophthalmic drug delivery. Adv Drug Deliv Rev 36: 59-79.
33. Loftsson T, Massen M (2001) Cyclodextrins in topical drug formulations: theory and practice. Int J Pharm 225: 15-30.
34. Loftsson T, Masson M, Sigurdsson HH, Magnusson P, Goffic FL (1998) Cyclodextrins as co-enhancers in dermal and transdermal drug delivery. Pharmazie 53: 137-139.
35. Loftsson T, Matthiasson K, Másson M (2003a) The effects of organic salts on the cyclodextrin solubilization of drugs. Int J Pharm 262: 101-107.
36. Loftsson T, Másson M (2004) The effects of water-soluble polymers on cyclodextrins and cyclodextrin solubilization of drugs. J Drug Del Sci Tech 14: 35-43.
37. Loftsson T, Másson M, Brewster ME (2004b) Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci 93: 1091-1099.
38. Loftsson T, Sigfusson SD, Sigurcrossed d signsson HH, Másson M (2003b) The effects of cyclodextrins on topical delivery of hydrocortisone: the aqueous diffusion layer. S.T.P. Pharma Sci 13: 125-131.
39. Loftsson T, Stefánsson E (1997) Effect of cyclodextrins on topical drug delivery to the eye. Drug Devel Ind Pharm 23: 473-481.
40. Loftsson T, Stefánsson E (2002) Cyclodextrins in eye drop formulations: enhanced topical delivery of corticosteroids to the eye. Acta Ophthalmol Scand 80: 144-150.
41. Loftsson T, Össurardottir ÍB, Duan M, Zhao N, Thorsteinsson T, Másson M (2005b) Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarban: effect of ionization and polymers. J Incl Phenom Macroc Chem 52: 109-117.
42. Magnusdottir A, Másson M, Loftsson T (2002) Self association and cyclodextrin solubilization of NSAIDs. J Incl Phenom Macroc Chem 44: 213-218.
43. Manosroi J, Apriyani MG, Foe K, Manosroi A (2005) Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hysroxypropyl-b-cyclodextrin. Int J Pharm 293: 235-240.
44. Masson M, Loftsson T, Masson G, Stefansson E (1999) Cyclodextrins as permeation enhancers: some theoretical evaluations and in vitro testing. J Control Rel 59: 107-118.
45. Matsuda H, Arima H (1999) Cyclodextrins in transdermal and rectal delivery. Adv Drug Deliv Rev 36: 81-99.
46. Másson M, Sigfússon SD, Loftsson T (2002) Fish skin as a model membrane to study transmembrane drug delivery with cyclodextrins. J Incl Phenom Macroc Chem 44: 177-182.
47. Másson M, Sigurdardóttir BV, Matthíasson K, Loftsson T (2005) Investigation of drug-cyclodextrin complexes by a phase-distribution method: some theoretical and practical considerations. Chem Pharm Bull 53: (in print).
48. Mele A, Mendichi R, Selva A (1998) Non-covalent associations of cyclomaltooligosaccharides (cyclodextrins) with trans-β-carotene in water: evidence for the formation of large aggregates by light scattering and NMR spectroscopy. Carbon Res 310: 261-267.
49. Merkus FWHM, Verhoef JC, Marttin E, Romeijn SG, van der Kuy PHM, Hermens WAJJ, Schipper NGM (1999) Cyclodextrin in nasal drug delivery. Adv Drug Deliv Rev 36: 41-57.
50. Moldenhauer J (2004) Personal communication: Octanol/water partition coefficients of cyclodextrins, Wacker-Chemie GmbH, Burghausen.
51. Mrestani Y, Mrestani-Klaus C, Bretschneider B, Neubert RHH (2004) Improvement of lipophilicity and membrane transport of cefuroxime using in vitro models. Eur J Pharm Biopharm 58: 653-657.
52. Neubert R, Fürst W (1989) In vitro-Untersuchungen des Arzneistofftransportes. Pharm uns Zeit 18: 112-124.
53. Preiss A, Mehnert W, Frömming K-H (1995) Penetration of hydrocortisone into excised human skin under the influence of cyclodextrins. Pharmazie 50: 121-126.
54. Preiss A, Mehnert W, Frömming KH (1994) In-vitro hydrocortisone release from ointments in presence of cyclodextrins. Pharmazie 49: 902-906.
55. Rao VM, Stella VJ (2003) When can cyclodextrins be considered for solubilizing purposes? J Pharm Sci 92: 927-932.
56. 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.
57. Saleh MA, Akhtar S, Begum S, Ahmed MS, Begum SK (2004) Density and viscosity of 1-alkanols. Phys Chem Liq 42: 615-623.
58. Siefert B, Keipert S (1997) Influence of a-cyclodextrin and hydroxyalkylated β-cyclodextrin derivatives on the in vitro comeal uptake and permeation of aqueous pilocarpine-HCl solutions. J Pharm Sci 86: 716-720.
59. Sinha VR, Bindra S, Kumria R, Nanda A (2003) Cyclodextrin as skin-penetration enhancers. Pharm Technol 27: 120-138.
60. Stella VJ, Rajewski RA (1997) Cyclodextrins: their future in drug formulation and delivery. Pharm. Res 14: 556-567.
61. Tanaka M, Iwata Y, Kouzuki Y, Taniguchi K, Matsuda H, Arima H, Tsuchiya S (1995) Effect of 2-hydroxypropyl-β-cyclodextrin on percutaneous absorption of methyl paraben. J Pharm Pharmacol 47: 897-900.
62. Tsutsumi K, Obata Y, Nagai T, Loftsson T, Takayama K (2002) Buccal absorption of ergotamine tartrate using bioadhesive tablet system in guinea pigs. Int J Pharm 238: 161-170.
63. Uekama K (2002) Recent aspects of pharmaceutical application of cyclodextrins. J Incl Phenom Macroc Chem 44: 3-7.
64. Uekama K, Arimori K, Sakai A, Masaki K, Me T, Otagiri M (1987) Improvement of percutaneous absorption of prednisolone by β- and γ-cyclodextrin complexations. Chem Pharm Bull 35: 2910-2913.
65. Uekama K, Hirayama F, Irie T (1998) Cyclodextrin drug carrier systems. Chem Rev 98: 2045-2076.
66. Vitória M, Bentley B, Renata F, Wilson S, Collett JH (1997) Characterization of the influence of some cyclodextrins on the stratum comeum from the hairless mouse. J Pharm Pharmacol 49: 397-402.
67. nd Ed., Taylor & Francis, London.
68. Williams AC, Barry BW (2004) Penetration enhancers. Adv Drug Deliv Rev 56: 603-618.
69. Yang T, Hussain A, Paulson J, Abbruscato TJ, Ahsan F (2004) Cyclodextrins in nasal delivery of low-molecular-weight heparins: in vivo and in vitro studies. Pharm Res 21: 1127-1136.
70. Zuo Z, Kwon G, Stevenson B, Diakur J, Wiebe LI (2000) Flutamide - hydroxypropyl-β-cyclodextrin complex: formulation, physical characterization, and absorption using the caco-2 in vitro model. J Pharm Pharmaceut Sci 3: 220-227.