Overcoming the nail barrier: A systematic investigation of ungual chemical penetration enhancement

International Journal of Pharmaceutics

Volumn 370, Issue 1-2, 2009, Pages 61-67

  Brown, M B ^a,b   Khengar, R H ^c   Turner, R B ^b   Forbes, B ^c   Traynor, M J ^a   Evans, C R G ^b   Jones, S A ^c  

^a UNIVERSITY OF HERTFORDSHIRE   (United Kingdom)

^b MEDPHARM LTD   (United Kingdom)

^c KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Drug permeation; Nail; Onychomycosis; Penetration enhancers; Ungual

Indexed keywords

CAFFEINE; KERATIN; METHYL PARABEN; OXIDIZING AGENT; PENETRATION ENHANCING AGENT; REDUCING AGENT; TERBINAFINE; THIOGLYCOLIC ACID; UNCLASSIFIED DRUG; UREA HYDROGEN PEROXIDE;

ADULT; AGED; ARTICLE; CELL DISRUPTION; CELL MEMBRANE PERMEABILITY; DISULFIDE BOND; DRUG PENETRATION; DRUG TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIPOPHILICITY; NAIL BED; NORMAL HUMAN; ONYCHOMYCOSIS; PERMEABILITY BARRIER; PRIORITY JOURNAL;

ABSORPTION; ADJUVANTS, PHARMACEUTIC; ADMINISTRATION, TOPICAL; ADOLESCENT; ADULT; AGED; CAFFEINE; CHEMISTRY, PHARMACEUTICAL; DIFFUSION CHAMBERS, CULTURE; DRUG COMBINATIONS; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; HUMANS; KINETICS; MIDDLE AGED; NAILS; NAPHTHALENES; PARABENS; PERMEABILITY; PEROXIDES; THIOGLYCOLATES; UREA;

EID: 61449148371     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2008.11.009     Document Type: Article

References (56)

1. Q2B. validation of analytical procedures: methodology. Proceedings of the International Conference on Harmonization (ICH), vol. 62. US FDA Federal Register (1997)
2. Q2A. text on validation of analytical procedures: definitions and terminology. Proceedings of the International Conference on Harmonisation (ICH), vol. 60. US FDA Federal Register (1995)
3. Ajit C., Suvannasankha A., Zaeri N., and Munoz S.J. Terbinafine-associated hepatotoxicity. Am. J. Med. Sci. 325 (2003) 292-295
4. Akomeah F., Nazir T., Martin G.P., and Brown M.B. Effect of heat on the percutaneous absorption and skin retention of three model penetrants. Eur. J. Pharm. Sci. 21 (2004) 337-345
5. Anfinsen C.B., and Haber E. Studies on the reduction and re-formation of protein disulfide bonds. J. Biol. Chem. 236 (1961) 1361-1363
6. Banning T.P., and Heard C.M. Binding of doxycycline to keratin, melanin and human epidermal tissue. Int. J. Pharm. 235 (2002) 219-227
7. Bommannan D., Potts R.O., and Guy R.H. Examination of the effect of ethanol on human stratum-corneum invivo using infrared-spectroscopy. J. Controlled Release 16 (1991) 299-304
8. Cammen L.M. Use of liquid scintillation-counting of cr-51 and c-14 in twin tracer method of measuring assimilation efficiency. Oecologia 30 (1977) 249-251
9. Cannell D.W. Permanent waving and hair straightening. Clin. Dermatol. 6 (1988) 71-82
10. Capozzi G., and Modena G. In: Patai S. (Ed). Oxidation of Thiols (1974), John Wiley and Sons Ltd. 785-840
11. Chambers W.M., Millar A., Jain S., and Burroughs A.K. Terbinafine-induced hepatic dysfunction. Eur. J. Gastroenterol. Hepatol. 13 (2001) 1115-1118
12. Dawber R.P.R. The ultrastructure and growth of human nails. Arch. Dermatol. Res. 269 (1980) 197-204
13. Denouel J., Keller H.P., Schaub P., Delaborde C., and Humbert H. Determination of terbinafine and its desmethyl metabolite in human plasma by high-performance liquid-chromatography. J. Chromatogr. B, Biomed. Appl. 663 (1995) 353-359
14. Einarson T.R., Gupta A.K., Shear N.H., and Arikian S. Clinical and economic factors in the treatment of onychomycosis. Pharmacoeconomics 9 (1996) 307-320
15. Elewski B.E. Onychomycosis: pathogenesis, diagnosis, and management. Clin. Microbiol. Rev. 11 (1998) 415-429
16. Gilbert H.F. Thiol/disulfide exchange equilibria and disulfide bond stability. Meth. Enzymol. 251 (1995) 8-28
17. Gniadecka M., Nielsen O.F., Christensen D.H., and Wulf H.C. Structure of water, proteins, and lipids in intact human skin, hair, and nail. J. Invest. Dermatol. 110 (1998) 393-398
18. Gonsalves A.M.D.R., Johnstone R.A.W., and Pereira M.M. Metal-assisted reactions. 21. Epoxidation of alkenes catalyzed by manganese-porphyrins-the effects of various oxidatively-stable ligands and bases. J. Chem. Soc. Perkin Trans. 1 (1991) 645-649
19. Grover C., Bansal S., Nanda S., Reddy B.S.N., and Kumar V. Combination of surgical avulsion and topical therapy for single nail onychomycosis: a randomized controlled trial. Br. J. Dermatol. 157 (2007) 364-368
20. Gunt H.B., and Kasting G.B. Effect of hydration on the permeation of ketoconazole through human nail plate in vitro. Eur. J. Pharm. Sci. 32 (2007) 254-260
21. Gupchup G.V., and Zatz J.L. Structural characteristics and permeability properties of the human nail: a review. J. Cosmet. Sci. 50 (1999) 363-385
22. Hao J.S., Smith K.A., and Li S.K. Chemical method to enhance transungual transport and iontophoresis efficiency. Int. J. Pharm. 357 (2008) 61-69
23. Hashiguchi T., Kodama A., Ryu A., and Otagiri M. Retention capacity of topical imidazole antifungal agents in the skin. Int. J. Pharm. 161 (1998) 195-204
24. Hui X.Y., Chan T.C.K., Barbadillo S., Lee C., Maibach H.I., and Wester R.C. Enhanced econazole penetration into human nail by 2-n-nonyl-1,3-dioxolane. J. Pharm. Sci. 92 (2003) 142-148
25. Hui X.Y., Shainhouse Z., Tanojo H., Anigbogu A., Markus G.E., Maibach H.I., and Wester R.C. Enhanced human nail drug delivery: nail inner drug content assayed by new unique method. J. Pharm. Sci. 91 (2002) 189-195
26. Jensen J.C. Clinical pharmacokinetics of terbinafine (Lamisil). Clin. Exp. Dermatol. 14 (1989) 110-113
27. Khengar R.H., Jones S.A., Turner R.B., Forbes B., and Brown M.B. Nail swelling as a pre-formulation screen for the selection and optimisation of ungual penetration enhancers. Pharm. Res. 24 (2007) 2207-2212
28. Kobayashi Y., Komatsu T., Sumi M., Numajiri S., Miyamoto M., Kobayashi D., Sugibayashi K., and Morimoto Y. In vitro permeation of several drugs through the human nail plate: relationship between physicochemical properties and nail permeability of drugs. Eur. J. Pharm. Sci. 21 (2004) 471-477
29. Kobayashi Y., Miyamoto M., Sugibayashi K., and Morimoto Y. Drug permeation through the three layers of the human nail plate. J. Pharm. Pharmacol. 51 (1999) 271-278
30. Kuzuhara A., and Hori T. Reduction mechanism of tioglycolic acid on keratin fibers using microspectrophotometry and FT-Raman spectroscopy. Polymer 44 (2003) 7963-7970
31. Lewis B.L. Microscopic studies of fetal and mature nail and surrounding soft tissue. A.M.A. Arch. Derm. Syphilol. 70 (1954) 732-747
32. Li Y. Biological properties of peroxide-containing tooth whiteners. Food Chem. Toxicol. 34 (1996) 887-904
33. Liew S.H. Unwanted body hair and its removal: a review. Dermatol. Surg. 25 (1999) 431-439
34. Maddock W.G., and Coller F.A. The role of the extremities in the dissipation of heat. Am. J. Physiol. 106 (1933) 589-596
35. Malhotra G.G., and Zatz J.L. Investigation of nail permeation enhancement by chemical modification using water as a probe. J. Pharm. Sci. 91 (2002) 312-323
36. Marshall R.C., Orwin D.F., and Gillespie J.M. Structure and biochemistry of mammalian hard keratin. Electron. Microsc. Rev. 4 (1991) 47-83
37. Megrab N.A., Williams A.C., and Barry B.W. Estradiol permeation across human skin, silastic and snake skin membranes-the effects of ethanol-water cosolvent systems. Int. J. Pharm. 116 (1995) 101-112
38. Mertin D., and Lippold B.C. In-vitro permeability of the human nail and of a keratin membrane from bovine hooves: prediction of the penetration rate of antimycotics through the nail plate and their efficacy. J. Pharm. Pharmacol. 49 (1997) 866-872
39. Mertin D., and Lippold B.C. In-vitro permeability of the human nail and of a keratin membrane from bovine hooves: influence of the partition coefficient octanol/water and the water solubility of drugs on their permeability and maximum flux. J. Pharm. Pharmacol. 49 (1997) 30-34
40. Mohorcic M., Torkar A., Friedrich J., Kristl J., and Murdan S. An investigation into keratinolytic enzymes to enhance ungual drug delivery. Int. J. Pharm. 332 (2007) 196-201
41. Murdan S. Drug delivery to the nail following topical application. Int. J. Pharm. 236 (2002) 1-26
42. Olsen E.A. Methods of hair removal. J. Am. Acad. Dermatol. 40 (1999) 143-155
43. Oltu U., and Gurgan S. Effects of three concentrations of carbamide peroxide on the structure of enamel. J. Oral. Rehabil. 27 (2000) 332-340
44. Robbins C.R. Chemical and Physical Behaviour of Human Hair. 4 Ed. (2002), Springer-Verlag, New York
45. Seebacher C. Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis. Mycoses 46 (2003) 506-510
46. Stinecipher J., and Shah J. Percutaneous permeation of N,N-diethyl-m-toluamide (DEET) from commercial mosquito repellents and the effect of solvent. J. Toxicol. Environ. Health 52 (1997) 119-135
47. Sun Y., Liu J.C., Wang J.C.T., and De Doncker P. In: Bronaugh R.L., and Maibach H.I. (Eds). Nail Penetration. Focus on Topical Delivery of Antifungal Drugs for Onychomycosis Treatment (1999), Marcel Dekker Inc., New York 759-787
48. Tatsumi Y., Yokoo M., Senda H., and Kakehi K. Therapeutic efficacy of topically applied KP-103 against experimental tinea unguium in guinea pigs in comparison with amorolfine and terbinafine. Antimicrob. Agents Chemother. 46 (2002) 3797-3801
49. Traynor M.J., Turner R.B., Evans C.R.G., Khengar R.H., Zhang L., Jones S.A., and Brown M.B. In: Brain K.R., and Walters K.A. (Eds). A Novel Permeation Enhancer Designed to Increase the Permeation of Currently Marketed Nail Lacquers Through Human Nail vol. 11 (2008), STS Publishing, Cardiff 90
50. vanHoogdalem E.J., vandenHoven W.E., Terpstra I.J., vanZijtveld J., Verschoor J.S.C., and Visser J.N. Nail penetration of the antifungal agent oxiconazole after repeated topical application in healthy volunteers, and the effect of acetylcysteine. Eur. J. Pharm. Sci. 5 (1997) 119-127
51. Walters K.A. Penetration of chemicals into, and through, the nail plate. Pharm. Int. 6 (1985) 86-89
52. Walters K.A., Flynn G.L., and Marvel J.R. Physicochemical characterization of the human nail-permeation pattern for water and the homologous alcohols and differences with respect to the stratum-corneum. J. Pharm. Pharmacol. 35 (1983) 28-33
53. Wessel S., Gniadecka M., Jemec G.B.E., and Wulf H.C. Hydration of human nails investigated by NIR-FT-Raman spectroscopy. Biochim. Biophys. Acta 1433 (1999) 210-216
54. Wickett R.R. Permanent waving and straightening of hair. Cutis 39 (1987) 496-497
55. Williams A.C. Transdermal and Topical Drug Delivery (2003), Pharmaceutical Press, London, UK
56. Wortmann F.J. Effects of the cuticle on the permanent wave set of human hair. J. Soc. Cosmet. Chem. 45 (1994) 149-158