An overview of skin penetration enhancers: Penetration enhancing activity, skin irritation potential and mechanism of action

Songklanakarin Journal of Science and Technology

Volumn 31, Issue 3, 2009, Pages 299-321

  Songkro, Sarunyoo ^a  

^a PRINCE OF SONGKLA UNIVERSITY   (Thailand)

Author keywords

Mechanism of action; Skin irritation; Skin penetration enhancer; Stratum corneum

Indexed keywords

EID: 71549151936     PISSN: 01253395     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (177)

1. Akimoto, T., Aoyagi, T., Minoshima, J.-I. and Nagase, Y. 1997. Polymeric percutaneous drug penetration enhancer-Synthesis and enhancing property of PEG/PDMS block copolymer with a cationic end group. Journal of Controlled Release. 49, 229-241.
2. Akimoto, T., Kawahara, K., Nagase, Y., and Aoyagi, T.2001. Polymeric transdermal drug penetration enhancer -The enhancing effect of oligodimethylsiloxane containing a glucopyranosyl end group. Journal of Controlled Release. 77, 49-57.
3. Akimoto, T. and Nagase, Y. 2003. Novel transdermal drug penetration enhancer: synthesis and enhancing effect of alkyldisiloxane compounds containing glucopyranosyl group. Journal of Controlled Release. 88, 243-252.
4. Al-Saidan, S. M., Barry, B. W. and Williams, A. C. 1998. Differential scanning calorimetry of human and animal stratum corneum membranes. International Journal of Pharmaceutics. 168, 17-22.
5. Anigbogu, A. N. C., Williams, A. C. Barry, B. W. and Edwards, H. G. M. 1995. Fourier transform Raman spectroscopy of interactions between the penetration enhancer dimethyl sulfoxide and human stratum corneum. International Journal of Pharmaceutics. 125, 265-282.
6. dos Anjos, J. L. V. and Alonso, A. 2008. Terpenes increase the partitioning and molecular dynamics of an amphipathic spin label in stratum corneum membranes. International Journal of Pharmaceutics. 350, 103-112.
7. Aoyagi, T., Terashima, O. Nagase Y. and Matsui, K. 1991. Preparation of a polymer containing hexadecylpyridinium bromide groups and its utilization as a transdermal drug penetration enhancer. Polymer. 32, 2106-2111.
8. Aoyagi, T., Terashima, O., Suzuki, N., Matsui, K. and Nagase, Y. 1990. Polymerization of benzalkonium chloridetype monomer and application to percutaneous drug absorption enhancer. Journal of Controlled Release. 13, 63-71.
9. Aqil, M., Ahad, A., Sultana, Y. and Ali, A. 2007. Status of terpenes as skin penetration enhancers. Drug Discovery Today. 12, 1061-1067.
10. Arellano, A., Santoyo, S., Martin, C. and Ygartua, P. 1996. Enhancing effect of terpenes on the in vitro percutaneous absorption of diclofenac sodium. International Journal of Pharmaceutics. 130, 141-145.
11. Asbill, C. S. and Michniak, B. B. 2000. Percutaneous penetration enhancers: Local versus transdermal activity. Pharmaceutical Science & Technology Today. 3, 36-41.
12. Ashton, P., Walters, K. A., Brain, K. R. and Hadgraft, J. 1992. Surfactant effects in percutaneous absorption. I: Effects on the transdermal flux of methyl nicotinate. International Journal of Pharmaceutics. 87, 261-264.
13. Attwood, D. and Florence, A. T. 1983. Surfactant Systems: Their Chemistry, Pharmacy and Biology, Chapman and Hall Ltd., London, U. K.
14. Aungst, B. 1995. Fatty acids as skin permeation enhancers. In Percutaneous Penetration Enhancers, E. W. Smith and H. I. Maibach, editors. CRC Press, Florida, U. S. A., pp 277-287.
15. Aungst, B. J., Rogers, N. J. and Shefter, E. 1986. Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides and amines. International Journal of Pharmaceutics. 33, 225-234.
16. Banga, A. K., Bose, S. and Ghosh, T. K. 1999. Iontophoresis and electroporation: comparisons and contrasts. International Journal of Pharmaceutics. 179, 1-19.
17. Barry, B. W. 1983. Dermatological Formulations: Percutaneous Absorption, Marcel Dekker, New York, U. S. A., pp 1-44.
18. Barry, B. W. 1987. Mode of action of penetration enhancers in human skin. Journal of Controlled Release. 6, 85-97.
19. Barry, B. W. 1991a. The LPP theory of skin penetration enhancement. In In Vitro Percutaneous Absorption: Principles, Fundamentals and Applications, R. L. Bronaugh and H. I. Maibach, editors. CRC Press, Florida, U. S. A., pp 165-185.
20. Barry, B. W. 1991b. Lipid-protein-partitioning theory of skin penetration enhancement. Journal of Controlled Release. 15, 237-248.
21. Barry, B. W. and Williams, A. C. 1993. Terpenes as skin penetration enhancers. In Pharmaceutical Skin Penetration Enhancement, K. A. Walters, and J. Hadgraft, editors. Marcel Dekker, New York, U. S. A., pp. 95-111.
22. Barry, B. W. and Williams, A. C. 1995. Permeation enhancement through skin. In Encyclopedia of Pharmaceutical Technology, J. Swarbrick and J. C. Boylan, editors. Marcel Dekker, New York, U. S. A., pp 449-493.
23. Bashir, S. J. and Maibach, H. I. 2001. In vivo irritation. In Handbook of Cosmetic Science and Technology, A. O. Barel, M. Paye and H. I. Maibach, editors. Marcel Dekker Inc., New York, U. S. A., pp 107-118.
24. Bennett, S. L., Barry, B. W. and Woodford, R. 1985. Optimization of bioavailability of topical steroids: nonoccluded penetration enhancers under thermodynamic control. Journal of Pharmacy and Pharmacology. 37, 298-304.
25. Ben-Shabat, S., Baruch, N. and Sintov, A.C. 2007. Conjugates of unsaturated fatty acids with propylene glycol as potentially less-irritant skin penetration enhancers. Drug Development and Industrial Pharmacy. 33, 1169-1175.
26. Bhatia, K. S. and Singh, J. 1998. Synergistic effect of iontophoresis and a series of fatty acids on LHRH permeability through porcine skin. Journal of Pharmaceutical Sciences. 87, 462-469.
27. Billmeyer, F.W. 1984. Introduction. In Textbook of Polymer Science, 3rd ed, F. W. Billmeyer, editor. A Wiley-Interscience Publication, John Wiley & Sons, New York, U. S. A., pp 3-21.
28. Bodde, H. E., Verhoeven, J. and van Driel, L. M. 1989. The skin compliance of transdermal drug delivery systems. Critical Reviews in Therapeutics Drug Carrier Systems. 6, 87-115.
29. Bounoure, F., Lahiani Skiba, M., Besnard, M., Arnaud, P., Mallet, E. and Skiba, M. 2008. Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine. Journal of Dermatological Science. 52, 170-177.
30. Bouwstra, J. A., Salomons-de Vries, M. A., van den Bergh, B. A. I. and Gooris, G. S. 1996. Changes in lipid organisation of the skin barrier by N-alkyl-azocycloheptanones: a visualisation and X-ray diffraction. International Journal of Pharmaceutics. 144, 81-89.
31. Bozdogan, B. and Appelbaum, P. C. 2004. Oxazolidinones: activity, mode of action, and mechanism of resistance. International Journal of Antimicrobial Agents. 23, 113-119.
32. Breuer, M. M. 1979. The interaction between surfactants and keratinous tissues. Journal of the Society of Cosmetic Chemists. 30, 41-64.
33. Byl, N. N. 1995. The use of ultrasound as an enhancer for transcutaneous drug delivery-phonophoresis. Physical Therapy. 75, 539-553.
34. Cázares-Delgadillo, J., Naik, A., Kalia, Y.N., Quintanar-Guerrero, D., and Ganem-Quintanar, A. 2005. Skin permeation enhancement by sucrose esters: A pH-dependent phenomenon. International Journal of Pharmaceutics. 297, 204-212.
35. Cevc, G. 2004. Lipid vesicles and other colloids as drug carriers on the skin. Advanced Drug Delivery Reviews. 56, 675-711.
36. Chattaraj, S. C. and Walker, R. B. 1995. Penetration enhancer classification. In Percutaneous Penetration Enhancers, E. W. Smith and H. I. Maibach, editors. CRC Press, Florida, U. S. A., pp 5-20.
37. Chowhan, Z. T. and Pritchard, R. 1978. Effect of surfactants on the percutaneous absorption of naproxen. I. Comparison of rabbit, rat and human excised skin. Journal of Pharmaceutical Sciences. 67, 1272-1274.
38. Clancy, M. J., Corish, J. and Corrigan, O. I. 1994. A comparison of the effects of electrical current and penetration enhancers on the properties of human skin using spectroscopic (FTIR) and calorimetric (DSC) methods. International Journal of Pharmaceutics. 105, 47-56.
39. Cornwell, P. A. and Barry, B. W. 1993. The route of penetration of ions and 5-fluorouracil across human skin and the mechanism of action of terpenes skin penetration enhancers. International Journal of Pharmaceutics. 94, 189-194.
40. Cornwell, P. A. and Barry, B. W. 1994. Sesquiterpene components of volatile oils as skin penetration enhancers for hydrophilic permeant 5-fluorouracil. Journal of Pharmacy and Pharmacology. 46, 261-269.
41. Cornwell, P. A. and Barry, B. W. 1995. Effects of penetration enhancer treatment on the statistical distribution of human skin permeabilities. International Journal of Pharmaceutics. 117, 101-112.
42. Cornwell, P. A., Barry, B. W., Stoddart, S. P. and Bouwstra, J. A. 1994. Wide-angle X-ray diffraction of human stratum corneum; effects of hydration and terpene enhancer treatment. Journal of Pharmacy and Pharmacology. 46, 938-950.
43. Cornwell, P. A., Barry, B. W., Bouwstra, J. A., Gooris, G. S. 1996. Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. International Journal of Pharmaceutics. 127, 9-26.
44. Davis, A. F., Gyurik, R. J., Hadgraft, J., Pellett, M. A. and Walters, K. A. 2002. Formulation strategies for modulating skin permeation. In Dermatological and Transdermal Formulations, vol. 119, K. A. Walters, editor. Marcel Dekker, New York, U. S. A., pp 271-317.
45. Dunn, R. L. Polymeric matrices. 1991. In Polymeric Drugs and Drug Delivery Systems, R. L. Dunn and R.M. Ottenbrite, editors. American Chemical Society, Washington, DC, U. S. A., pp 11-23.
46. Ebert, C. D., Patel, D. and Heiber, W. 1992. Method and device for transdermally administering testosterone across nonscrotal skin at therapeutically effective levels. United States Patent 5,152,997.
47. Elias, P. M. 1981. Epidermal lipids, membranes and keratinization. International Journal of Dermatology. 20, 1-19.
48. Elias, P. M. and Leventhal, M. E. 1980. Intercellular volume changes and cell surface area expansion during cornification. European Journal of Cell Biology. 22, 439A.
49. El-Kattan, A. F., Asbill, C. S. and Michniak, B. B. 2000. The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel system. International Journal of Pharmaceutics. 198, 179-189.
50. El-Kattan, A. F., Asbill, C. S., Kim, N. and Michniak, B. B. 2001. Effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities. International Journal of Pharmaceutics. 215, 229-240.
51. Falbe, J. 1987. Surfactants in Consumer Products, Springer-Verlag, Heidelberg, Germany.
52. Fang, J. Y., Hwang, T. L., Fang, C. L. and Chiu, H. C. 2003a. In vitro and in vivo evaluations of the efficacy and safety of skin permeation enhancers using flurbipro flurbiprofen as a model drug. International Journal of Pharmaceutics. 255, 153-166.
53. Fang, J. Y., Leu, Y. L., Hwang, T. L., Cheng, H. C. and Hung, C. F. 2003b. Development of sesquiterpenes from Alpinia oxyphylla as novel skin permeation enhancers. European Journal of Pharmarceutical Sciences. 19, 253-262, 2003.
54. Finnin, B. C. and Morgan, T. M. 1999. Transdermal penetration enhancers: application limitations and potential. Journal of Pharmaceutical Sciences. 88, 955-958.
55. Francoeur, M. L., Golden, G. M. and Potts, R. O. 1990. Oleic acid: the effects on stratum corneum in relation to (trans) dermal drug delivery. Pharmaceutical Research. 7, 621-627.
56. Ganem-Quintanar, A., Quintanar-Guerrero, D. and Buri, P. 2000. Monoolein: a review of the pharmaceutical applications. Drug Development and Industrial Pharmacy. 26, 809-820.
57. Gao, S. and Singh, J. 1997. Mechanism of transdermal transport of 5-fluorouracil by terpenes-carvone, 1, 8-cineole and thymol. International Journal of Pharmaceutics. 154, 67-77.
58. Ghafourian, T., Zandasrar, P., Hamishekar, H. and Nokhodchi, A. 2004. The effect of penetration enhancers on drug delivery through skin: a QSAR study. Journal of Controlled Release. 99, 113-125.
59. Ghosh, T. K. and Banga, A. K. 1993. Methods of enhancement of transdermal drug delivery: Part II. A chemical permeation enhancers. Pharmaceutical Technology. 4, 62-90.
60. Giannakou, S. A., Dallas, P. P. Rekkas D. M. and Choulis, N. H. 1995. Development and in vitro evaluation of nitrendipine transdermal formulations using experimental design techniques. International Journal of Pharmaceutics. 125, 7-15.
61. Godwin, D. A. and Michniak, B. B. 1999 Influence of drug lipophilicity on terpenes as transdermal penetration enhancers. Drug Development and Industrial Pharmacy. 25, 905-915.
62. Golden, G. M., Guzek, D. B., Harris, R. R., McKie, J. E. and Potts, R.O. 1986. Lipid thermotropic transitions in human stratum corneum. Journal of Investigative. Dermatology. 86, 255-259.
63. Goodman, M. and Barry, B. W. 1986. Differential scanning calorimetry of human stratum corneum effects of penetration enhancers azone and dimethyl sulphoxide. Analytical Proceedings. 23, 397-398.
64. Govil, S. K., Rudnic, E. M., Sterner, D. G. 1993. Transdermal nitroglycerin patch with penetration enhancers. United States Patent 5, 262, 165.
65. Gunatillake, P., Mayadunne, R. and Adhikari, R. 2006. Recent developments in biodegradable synthetic polymers. Biotechnology Annual Review. 12, 301-347.
66. Guy, R. H. and Hadgraft, J. 1987. The effect of penetration enhancers on the kinetics of percutaneous absorption. Journal of Controlled Release. 5, 43-51.
67. Guy, R. H. and Hadgraft, J. 1989. Selection of drug candidates for transdermal drug delivery. In Transdermal Drug Delivery: Developmental Issues and Research Initiatives, J. Hadgraft and R. H. Guy, editors. Marcel Dekker, New York, U. S. A., pp 59-81.
68. Hadgraft, J. 1999. Passive enhancement strategies in topical and transdermal drug delivery. International Journal of Pharmaceutics. 184, 1-6.
69. Hadgraft, J. 2001. Skin, the final frontier. International Journal of Pharmaceutics. 224, 1-18.
70. Haigh, J. M. and Smith, E. W. 1995. Hydration and topical corticosteroid absorption. In Percutaneous Penetration Enhancers, E. W. Smith and H. I. Maibach, editors. CRC Press, Florida, U. S. A., pp 29-34.
71. Harrison, J. E., Watkinson, A. C., Green, D. M., Hadgraft, J. and Brain, K. 1996. The relative effect of Azone and Transcutolon permeant diffusivity and solubility in human stratum corneum. Pharmaceutical Research. 13, 542-546.
72. Hashida, M. and Yamashita, F. Terpenes as penetration enhancers. 1995. In Percutaneous Penetration Enhancers, E. W. Smith, editor. CRC Press, Florida, U. S. A., pp. 309-321.
73. Heard, C. M. Kung, D. and Thomas, C.P. 2006. Skin penetration enhancement of mefenamic acid by ethanol and 1, 8-cineole can be explained by the 'pull' effect. International Journal of Pharmaceutics. 321, 167-170.
74. Henry, S., McAllister, D. V., Allen, M. G. and Prausnitz, M. R. 1998. Microfabricated microneedles: a novel approach to transdermal drug delivery. Journal of Pharmaceutical Sciences. 87, 922-925.
75. Herai, H., Gratieri, T., Thomazine, J. A., Bentley M. V. L. B. and Lopez, R. F. 2007. Doxorubicin skin penetration from monoolein-containing propylene glycol formulations. International Journal of Pharmaceutics. 329, 88-93.
76. Hori, M., Satosh, S. and Maibach, H. I. 1989. Classification of percutaneous penetration enhancers: A conceptual diagram. In Percutaneous Absorption: Mechanisms, Methodology, Drug Delivery, R. L. Bronaugh and H. I. Maibach, editors. Marcel Dekker, New York, U. S. A., pp 197-211.
77. Hsu, L. R., Huang, Y. B., Wu, P. C. and Tsai, Y. H. 1994. Percutaneous absorption of piroxicam from FAPG Base through rat skin-effects of fatty acid added to FAPG Base. International Journal of Pharmaceutics. 106, 1-6.
78. Huang, Y. B., Fang, J. Y., Hung, C. H., Wu, P. C., Tsai, Y. H. 1999. Cyclic monoterpene extract from cardamom oil as a skin permeation enhancer for indomethacin: In vitro and in vivo studies. Biological and Pharmaceutical Bulletin. 22, 642-646.
79. Huang, Y. B., Wu, P. C., Ko, H. M. and Tsai, Y. H. 1995. Cardamom oil as a skin permeation enhancer for indomethacin piroxicam and diclofenac. International Journal of Pharmaceutics. 126, 111-117.
80. Hwang, C. C. and Danti, A. G. 1983. Percutaneous absorption of flufenamic acid in rabbits: Effect of dimethyl sulfoxide and various nonionic surfactants. Journal of Pharmaceutical Sciences. 72, 857-860.
81. Imokawa, G., Akasaki, S., Minematsu, Y. and Kawai, M. 1989. Importance of intercellular lipids in water-retention properties of the stratum corneum: induction and recovery study of surfactant dry skin. Archives of Dermatological Research. 281, 45-51
82. Jantharaprapap, R. and Stagni, G. 2007. Effects of penetration enhancers on in vitro permeability of meloxicam gels. International Journal of Pharmaceutics. 343, 26-33.
83. Kadir, R., Tiemessen, H. L. G. M., Ponec, M., Junginger, H. E. and Bodde, H. E. 1993. Oleeyl surfactants as skin penetration enhancers: Effects on human stratum corneum permeability and in vitro toxicity to cultured human skin cells. In Pharmaceutical Skin Penetration Enhancement, K. A. Waters and J. Hadgraft, editors. Marcel Dekker, Inc., New York, U. S. A., pp 215-227.
84. Kanikkannan, N., Babu, R. J. and Singh, M. 2006. StructureActivity Relationship of chemical penetration enhancers. In Percutaneous Penetration Enhancers, 2nd ed., E. W. Smith and H. I. Maibach, editors. CRC Press, Florida, U. S. A., pp 17-32.
85. Karande, P. and Mitragotri, S. 2002. High throughput screening of transdermal formulations. Pharmaceutical Research. 19, 655-660.
86. Karande, P., Jain, A. and Mitragotri, S. 2004. Discovery of transdermal penetration enhancers by high-throughput screening. Nature Biotechnology. 22, 192-197.
87. Kawasaki, Y., Quan, D., Sakamoto, K. and Maibach, H. I. 1997. Electron resonance studies on the influence of anionic surfactants on human skin. Dermatology. 194, 238-242.
88. Kim, Y. C., Park, J. H., Ludovice, P. J. and Prausnitz, M. R. 2008. Synergistic enhancement of skin permeability by N-lauroylsarcosine and ethanol. International Journal of Pharmaceutics. 352, 129-138.
89. Kimura, C., Nakanishi, T. and Tojo, K. 2007. Skin permeation of ketotifen applied from stick-type formulation. European Journal of Pharmaceutics and Biopharmaceutics. 67, 420-424.
90. Knutson, K., Potts, R. O., Guzek, D. B., Golden, G. M., McKie, J. E., Lambert, W. J., Higuchi, W. I. 1985. Macro-and molecular physical-chemical considerations in understanding drug transport in the stratum corneum. Journal of Controlled Release. 2, 67-87.
91. Kobayashi, D., Matsuzawa, T., Sugibayashi, K. Y. M. and Kimura, M. 1994. Analysis of the combined effect of l-menthol and ethanol as skin permeation enhancers based on a two-layer skin model. Pharmaceutical Research. 11, 96-103.
92. Komata, Y., Inaoka, M., Kaneko, A. and Fujie, T. 1992. In vitro percutaneous absorption of thiamine disulfide from a mixture of propylene glycol and fatty acid. Journal of Pharmaceutical Sciences. 81, 744-746.
93. Kunta, J. R., Goskonda, V. R., Brotherton, H. O., Khan, M. A. and Reddy, I. K. 1997. Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. Journal of Pharmaceutical Sciences. 86, 1369-1373.
94. Kushla, G. P., Zatz, J. L., Mills, O. H. J. and Berger, R. S. 1993. Noninvasive assessment of anaesthetic activity of topical lidocaine formulations. Journal of Pharmaceutical Sciences. 82, 1118-1122.
95. Lambert, W. J., Kudla, R. J., Holland, J. M. and Curry, J. T. 1993. A biodegradable transdermal penetration enhancer based on N-(2-hydroxyethyl)-2-pyrrolidone I. Synthesis and characterization. International Journal of Pharmaceutics. 95, 181-192.
96. Larrucea, E., Arellano, A., Santoyo, S. and Ygartua, P. 2001. Combined effect of oleic acid and propylene glycol on the percutaneous penetration of tenoxicam and its retention in the skin. European Journal of Pharmaceutics and Biopharmaceutics. 52, 113-119.
97. Lee, W. R., Shen, S. C., Fang, C. L., Zhuo, R. Z. and Fang, J. Y. 2008. Topical delivery of methotrexate via skin pretreated with physical enhancement techniques: low-fluence erbium:YAG laser and electroporation. Lasers in Surgery and Medicine. 40, 468-476.
98. Levang, A. K., Zhao, K. and Singh, J. 1999. Effect of ethanol/ propylene glycol on the in vitro percutaneous absorption of aspirin, biophysical changes and macroscopic barrier properties of the skin. International Journal of Pharmaceutics. 181, 255-263.
99. Liron, Z. and Cohen, S. 1984. Percutaneous absorption of alkanoic acids II: Application of regular solution theory. Journal of Pharmaceutical Sciences. 73, 538-542.
100. Loftsson, T., Gildersleeve, N. and Bodor, N. 1987. The effect of vehicle additives on the transdermal delivery of nitroglycerin. Pharmaceutical Research. 4, 436-437.
101. Lopes, L. B. Collett, J. H. and Bentley M. V. L. B. 2005. Topical delivery of cyclosporine A: an in vitro study using monoolein as a penetration enhancer. European Journal of Pharmaceutics and Biopharmaceutics. 60, 25-30.
102. Lopes, L. B., Lopes, J. L. C., Oliveira, D. C. R., Thomazini, J. A., Garcia, M. T. J., Fantini, M. C. A., Collett, J. H. and Bentley, M. V. L. B. 2006. Liquid crystalline phases of monoolein and water for topical delivery of cyclosporine A: Characterization and study of in vitro and in vivo delivery. European Journal of Pharmaceutics and Biopharmaceutics. 63, 146-155.
103. Lopes, L. B, Speretta, F. F. and Bentley, M. V. L. B. 2007. Enhancement of skin penetration of vitamin K using monoolein-based liquid crystalline systems. European Journal of Pharmaceutical Sciences. 32, 209-215.
104. López, A., Llinares, F., Cortell, C. and Herráez, M. 2000. Comparative enhancer effects of Span 20 with Tween 20 and Azone on the in vitro percutaneous penetration of compounds with different lipophilicities. International Journal of Pharmaceutics. 202, 133-140.
105. Lu, M. F., Lee, D. and Rao, G. S. 1992. Percutaneous absorption enhancement of leuprolide. Pharmaceutical Research. 9, 1575-1579.
106. Magnusson, B. M., Runn, P., Karlsson, K. and Koskinen, L. O. D. 1997. Terpenes and ethanol enhance the transdermal permeations of the tripeptide thyrotropin releasing hormone in human epidermis. International Journal of Pharmaceutics. 157, 113-121.
107. Mak, V. H. W., Potts, R. O. and Guy, R. H. 1990. Percutaneous penetration enhancement in vivo measured by attenuated total reflectance infrared spectroscopy. Pharmaceutical Research. 7, 835-841.
108. McDougal, J. N., Council, E. A. and Powers, B. S. 2007. Systemic toxicity from skin exposures (or what happens when you do not decontaminate). Journal of Chemical Health and Safety. 14, 23-31.
109. Mizushima, J., Kawasaki, Y., Tabohashi, T., Kitano, T., Sakamoto, K., Kawashima, M., Cooke, R. and Maibach, H. I. 2000.Effect of surfactants on human stratum corneum: electron paramagnetic resonance study. International Journal of Pharmaceutics. 197, 193-202.
110. Moghimi, H. R., Williams, A. C. and Barry, B. W. 1996. A lamellar matrix model for stratum corneum intercellular lipids IV. Effects of terpene penetration enhancers on the permeation of 5-fluorouracil and oestradiol through the matrix. International Journal of Pharmaceutics. 145, 49-59.
111. Morimoto, K., Tojima, H., Haruta, T., Suzuki, M. and Kakemi, M. 1996. Enhancing effect of unsaturated fatty acids with various structures on the permeation of indomethacin through rat skin. Journal of Pharmacy and Pharmacology. 48, 1133-1137.
112. Moser, K., Kriwet, K., Naik, A., Kalia, Y. N. and Guy, R. H. 2001. Passive skin penetration enhancement and its quantification in vitro. European Journal of Pharmaceutics and Biopharmaceutics. 52, 103-112.
113. Murthy, S. N. and Hiremath, S. R. R. 2001. Physical and chemical permeation enhancers in transdermal delivery of terbutaline sulphate. AAPS PharmSciTech. 2, e1-e5.
114. Naik, A., Kalia, Y. N. and Guy, R. H. 2000. Transdermal drug delivery: overcoming the skin's barrier function. Pharmaceutical Science & Technology Today. 3, 318-326.
115. Niazy, E. M. 1991. Influence of oleic acid and other permeation promoters on transdermal delivery of dihydroergotamine through rabbit skin. International Journal of Pharmaceutics. 67, 97-100.
116. Nokhodchi, A., Shokri, J., Dashbolaghi, A., Hassan-Zadeh, D., Ghafourian, T. and Barzegar-Jalali, M. 2003. The enhancement effect of surfactants on the penetration of lorazepam through rat skin. International Journal of Pharmaceutics. 250, 359-369.
117. Nokhodchi, A., Sharabiani, K., Rashidi M. R. and Ghafourian, T. 2007. The effect of terpene concentrations on the skin penetration of diclofenac sodium. International Journal of Pharmaceutics. 335, 97-105.
118. Obata, Y., Takayama, K., Machida, Y. and Nagai, T. 1991. Combined effect of cyclic monoterpenes and ethanol on percutaneous absorption of diclofenac sodium. Drug Design and Discovery. 8, 137-144.
119. Ogiso, T., Hata, T., Iwaki, M., Tanino, T. 2001. Transdermal absorption of bupranolol in rabbit skin in vitro and in vivo. Biological and Pharmaceutical Bulletin. 24, 588-591.
120. Ogiso, T. and Shintani, M. 1990. Mechanism for the enhancement effect of fatty acids on the percutaneous absorption of propranolol. Journal of Pharmaceutical Sciences. 79, 1065-1071.
121. Ogiso, T., Iwaki, M. and Paku, T. 1995. Effect of various enhancers on transdermal penetration of indomethacin and urea, and relationship between penetration parameters and enhancement factors. Journal of Pharmaceutical Sciences. 84, 482-488.
122. Oh, H. J., Oh, Y. K. and Kim, C. K. 2001. Effects of vehicles and enhancers on transdermal delivery of melatonin. International Journal of Pharmaceutics. 212, 63-71.
123. Okabe, H., Obata, Y., Takayama, K. and Nagai, T. 1990. Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes. Drug Design and Delivery. 6, 229-238.
124. Okabe, H., Takayama, K. and Nagai, T. 1992. Percutaneous absorption of ketoprofen from acyclic gel patches containing D-limonene and ethanol as absorption enhancers. Chemical and Pharmaceutical Bulletin. 40, 1906-1910.
125. Ongpipattanakul, B., Burnette, R. R., Potts, R. O. and Francoeur, M. L. 1991. Evidence that oleic acid exists in a separate phase within stratum corneum lipids. Pharmaceutical Research. 8, 350-354.
126. Osborne, D. W. and Henke, J. J. 1997. Skin penetration enhancers cited in the technical literature. Pharmaceutical Technology. 11, 58-66.
127. Otberg, N., Patzelt, A., Rasulev, U., Hagemeister, T., Linscheid, M. Sinkgraven, R., Sterry, W. and Lademann, J. 2008. The role of hair follicles in the percutaneous absorption of caffeine. British Journal of Clinical Pharmacology. 65, 488-492.
128. Panchagnula, R., Bokalial, R., Sharma, P. and Khandavilli, S. 2005. Transdermal delivery of naloxone: skin permeation, pharmacokinetic, irritancy and stability studies. International Journal of Pharmaceutics. 293, 213-223.
129. Pellett, M. A., Davies, A. F. and Hadgraft, J. 1994. Effect of supersaturation on membrane transport: II. Piroxicam. International Journal of Pharmaceutics. 111, 1-6.
130. Pereira, G. R. Collett, J. H. Garcia, S. B. Thomazini, J. A. and Bentley, M. V. L. B. 2002. Glycerol monooleate/ solvents systems for progesterone transdermal delivery: in vitro permeation and microscopic studies. Brazilian Journal of Pharmaceutical Sciences. 38, 55-62.
131. Pfister, W. R., and Hsieh, D. S. 1990a. Permeation enhancers compatible with transdermal drug delivery system. Part I. Selection and formulation considerations. Medical Device Technology. 1, 48-55.
132. Pfister, W. R. and Hsieh, D. S. 1990b. Permeation enhancers compatible with transdermal drug delivery system. Part II. System design considerations. Medical Device Technology. 1, 28-33.
133. Pfister, W. R. and Rajadhyaksha, V. J. 1995. Oxazolidinones: a new class of cyclic urethane transdermal enhancer (CUTE). Pharmaceutical Research. 12, S-280.
134. Phillips, C. A. and Michniak, B. B. 1995.Topical application of Azone analogs to hairless mouse skin: A histopathological study. International Journal of Pharmaceutics. 125, 63-71.
135. Quan, D., Cooke, R. A. and Maibach, H. I. 1995. An electron spin resonance study of human epidermal lipids using 5-doxyl stearic acid. Journal of Controlled Release. 36, 235-241.
136. Quan, D. and Maibach, H. I. 1994. An electron spin resonance study: I. Effect of Azone on 5-doxyl stearic acidlabeled human stratum corneum. International Journal of Pharmaceutics. 104, 61-72.
137. Rachakonda, V. K., Yerramsetty, K. M., Madihally, S. V., Robinson Jr., R. L. and Gasem, K. A. M. 2008. Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin. Pharmaceutical Research. 25, 11, 2697-2704.
138. Rajadhyaksha, V. J. 1990. Oxazolidinone penetration enhancing compounds, US Patent 4, 960, 771.
139. Rajadhyaksha V. J. and Pfister, W.R. 1996. Oxazolidinones: optimizing delivery of active ingredients in skin care products. Drug & Cosmetic Industry. 158, 36-47.
140. Rajadhyaksha, V. J., Sharma, K. and Pfister, W. R. 1997. Oxazolidinones: a new class of permeation enhancer. In Transdermal and Topical Drug Delivery Systems, T. K. Ghosh, W. R. Pfister and S. I. Yum, editors. Informa HealthCare, New York, U. S. A., pp 477-509.
141. Ren, C., Fang, L., Li, T., Wang, M., Zhao, L. and He, Z. 2008. Effect of permeation enhancers and organic acids on the skin permeation of indapamide. International Journal of Pharmaceutics. 350, 43-47.
142. Rhee, Y. S., Choi, J. S. and Park, E. S. 2001. Transdermal delivery of ketoprofen using microemulsions. International Journal of Pharmaceutics. 228, 161-170.
143. Rhein, L. D., Robbins, C. R., Fernee, K. and Cantore, R. 1986. Surfactant structure effects on swelling of isolated human stratum corneum. Journal of the Society of Cosmetic Chemists. 37, 125-139.
144. Robinson, M. K., Osborne, R. and Perkins, M. A. 2001. In vitro tests for skin Irritation. In Handbook of Cosmetic Science and Technology, A. O. Barel, M. Paye, H. I. Maibach, editors. Marcel Dekker Inc., New York, U. S. A., pp 95-106.
145. Santus, G. C., Baker, R. W. 1993. Transdermal enhancer patent literature. Journal of Controlled Release. 25, 1-20.
146. Sarpotdar, P. P. and Zatz, J. L. 1986a. Evaluation of penetration enhancement of lidocaine by nonionic surfactants through hairless mouse skin in vitro. Journal of Pharmaceutical Sciences. 75, 176-181.
147. Sarpotdar, P. P., and Zatz, J. L. 1986b. Percutaneous absorption enhancement by nonionic surfactants. Drug Development and Industrial Pharmacy. 12, 1625-1647.
148. Scheuplein, R. J. and Blank, I. H. 1971. Permeability of the skin. Physiological Reviews. 51, 702-747.
149. Schneider, I. M., Dobner, B., Neubert, R., and Wohlrab, W. 1996. Evaluation of drug penetration into human skin ex vivo using branched fatty acids and propylene glycol. International Journal of Pharmaceutics. 145, 187-196.
150. Seki, T., Kawaguchi, T., Sugibayashi, K., Juni, K., and Morimoto, Y. 1989. Percutaneous absorption of azidothymidine in rats. International Journal of Pharmaceutics. 57, 73-75.
151. Shah, J. C., Sadhale, Y. and Chilukuri, D. M. 2001. Cubic phase as drug delivery systems. Advanced Drug Delivery Review. 47, 229-250.
152. Shen, W. W., Danti, A. G. and Bruscato, F. N. 1976. Effect of nonionic surfactants on percutaneous absorption of salicylic acid and sodium salicylate in the presence of dimethylsulfoxide. Journal of Pharmarceutical Sciences. 65, 1780-1783.
153. Shokri, J., Nokhodchi, A., Dashbolaghi, A., Hassan-Zadeh, D., Ghafourian, T. and Barzeger Jalali, M. 2001. The effect of surfactants on the skin penetration of diazepam. International Journal of Pharmaceutics. 228, 99-107.
154. Smyth, H. D., Becket, G., Mehta, S. 2002. Effect of permeation enhancer pretreatment on the iontophoresis of luteinizing hormone releasing hormone (LHRH) through human epidermal membrane (HEM). Journal of Pharmaceutical Sciences. 91, 1296-1307.
155. Songkro S., Rades, T. and Becket, G. 2003. The effects of pmenthane monoterpenes and related compounds on the percutaneous absorption of propranolol hydrochlo-ride across newborn pig skin. I. In vitro skin permeation and retention studies. S.T.P. Pharma Sciences. 13, 349-357.
156. Songkro, S., Wungsintaweekul, J. and Chartwaingam, S. 2008. Investigation of enhancing activity and skin irritation of Zingiber officinale, Zingiber cassumunar and Curcuma zedoaria. Journal of Drug Delivery Science and Technology. 18, 169-179.
157. Sugibayashi, K. and Morimoto, Y. 1994. Polymers for transdermal drug delivery systems. Journal of Controlled Release. 29, 177-185
158. Takayama, K. and Nagai, T. 1994. Limonene and related compounds as potential skin penetration promoters. Drug Development and Industrial Pharmacy. 20, 677-684.
159. Tanner, T. and Marks, R. 2008. Delivering drugs by the transdermal route: review and comment. Skin Research and Technology. 14, 249-260.
160. Tanojo, H., Boelsma, E., Junginger, H. E., Ponec, M. and Bodde, H. E. 1998. In vivo human skin barrier modulation by topical application of fatty acids. Skin Pharmacology and Applied Skin Physiology. 11, 87-97.
161. Tao, S. L. and Desai, T. A. 2003. Microfabricated drug delivery systems: from particles to pores. Advanced Drug Delivery Reviews. 55, 315-328.
162. Thong, H. Y. Zhai, H. and Maibach H. I. 2007. Percutaneous penetration enhancers: an overview. Skin Pharmacology and Physiology. 20, 272-282.
163. Touitou, E., Godin, B., Karl, Y., Bujanover, S. and Becker, Y. 2008. Oleic acid, a skin penetration enhancer, affects Langerhans cells and corneocytes. Journal of Controlled Release. 80, 1-7.
164. Trommer, H., Neubert, R. H. H. 2006. Overcoming the stratum corneum: the modulation of skin penetration. A review. Skin Pharmacology and Physiology. 19, 106-121.
165. Tupker, R. A., Pinnagoda, J. and Nater, J. P. 1990. The transient and cumulative effect of sodium lauryl sulphate on the epidermal barrier assessed by transepidermal water loss: interindividual variation. Acta Dermato-Venereologica. 70, 1-5.
166. Turchiello, R. F., Vena, F. C. B., Maillard, Ph., Souza, C. S., Bentley M. V. L. B and Tedesco, A. C. 2003. Cubic phase gel as a drug delivery system for topical application of 5-ALA, its ester derivatives and m-THPC in photodynamic therapy (PDT). Journal of Photochemistry and Photobiology B: Biology. 70, 1-6.
167. Vaddi, H. K., Ho, P. C. and Chan, S. Y. 2002a. Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes. Journal of Controlled Release. 81, 121-133.
168. Vaddi, H. K., Ho, P. C. and Chan, S. Y. 2002b. Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. Journal of Pharmaceutical Sciences. 91, 1639-1651.
169. Venuganti, V. V. K. and Perumal, O. P. 2008. Effect of poly(amidoamine) (PAMAM) dendrimer on skin permeation of 5-fluorouracil. International Journal of Pharmaceutics. 361, 230-238.
170. Walker, M. and Hadgraft, J. 1991. Oleic acid -a membrane 'fluidizer' or fluid within the membrane? International Journal of Pharmaceutics. 71, R1-R4.
171. Walters, K. A. 1989. Penetration enhancers and their use in transdermal therapeutic systems. In Transdermal Drug Delivery: Developmental Issues and Research Initiatives. J. Hadgraft and R. H. Guy, editors. Marcel Dekker, New York, U.S.A., pp 197-246.
172. Walters, K. A. 1990. Surfactants and percutaneous absorption. In Prediction of Percutaneous Penetration: Methods, Measurements, Modelling, R. C. Scott, R. H. Guy and J. Hadgraft, editors. IBC Technical Services Ltd., London, U. K., pp 148-162.
173. Walters, K. A., Florence, A. T. and Dugard, P.H. 1982. Interaction of polyoxethylene alkyl ethers with cholesterol monolayers. Journal of Colloid and Interface Science. 89, 584-587.
174. Willams, A. C. and Barry, B. W. 1989. Permeation, FTIR and DSC Investigations of terpene penetration enhancers in human skin. Journal of Pharmacy and Pharmacology. 41(Suppl.), 12P.
175. Williams, A. C. and Barry, B. W. 1991a. Terpenes and the lipid-protein-partitioning theory of skin penetration enhancement. Pharmaceutical Research. 8, 17-24.
176. Williams, A. C. and Barry, B. W. 1991b. The enhancement index concept applied to terpene penetration enhancer for human skin and model lipophilic (oestradiol) and hydrophilic (5 fluorouracil) drugs. International Journal of Pharmaceutics. 74, 157-168.
177. Williams, A. C. and Barry, B. W. 2004. Penetration enhancers. Advanced Drug Delivery Reviews. 56, 603-618.