Effect of Terpenes on the Skin Permeation of Ketoprofen through Shed Snake Skin
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terpenes transdermal delivery ketoprofen shed snake skin
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Abstract
The objective of this work was to investigate the effect of hydrocarbon (a-pinene and limonene) andoxygen containing monoterpenes (carvone and terpineole) at 5%w/v in hydroalcoholic mixtures (50% ethanol)on the permeation of ketoprofen across shed snake skin of Python molurus bivittatus. The amount of KPretained in the skin after 8 h of diffusion was determined. It was found that the percutaneous absorption ofketoprofen was enhanced in the presence of the enhancers. The rank order of enhancement ratio for skinpermeation was found to be a-pinene > limonene > carvone > terpinoele. The enhancers also affected theretention of KP in the skin. The rank order of enhancement ratio for skin retention was the same order with skinpermeation experiment. The results indicated that that lipophilicity is an important structural feature formonoterpenes as skin permeation enhancer for a liphophilic drug, ketoprofen.
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Bilek, H., Wonglertnirant, N., Ngawhirunpat, T., Opanasopit, P., & Vollrath, M. K. .-. (2013). Effect of Terpenes on the Skin Permeation of Ketoprofen through Shed Snake Skin. Science, Engineering and Health Studies, 3(2), 33–41. https://doi.org/10.14456/sustj.2009.7
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Research Articles
References
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Barry, B. W. (1987). Mode of action of penetration enhancers in human skin. Journal of Controlled Release, 6: 85-97.
Bergstrom, K., Bergstrom, T., Knustson, K., Denoble,L.J., and Goates, C. Y. (1990). Percutaneous absorption enhancement of a ionic molecule by ethanol-water systems in human skin. Pharmaceutical Research, 7: 762-766.
Borras-Blasco, J., Lopez, A., Morant, M. J., Diez-Sales, O., and Herraez-Dominguez, M. (1996). Influence of sodium lauryl sulphate on the in vitro percutaneous absorption of compound with different lipophilicity. European Journal of Pharmaceutical Sciences, 5: 15-22.
Borras-Blasco, J., Diez-Sales, O., Lopez, A., and Herraez-Dominguez, M. (2004). A mathematical approach to predicting the percutaneous absorption enhancing effect of sodium lauryl sulphate. International Journal of Pharmaceutics, 269: 121-129.
Knutson, K., Potts, R. O., Guzek, D. B., Golden, G. M., Mckie, J. E., Lambert, W. J., and Higuchi W. I. (1985). Macro and molecular physical-chemical consideration in understanding drug transport in stratum corneum. Journal of Controlled Release, 2: 67-87.
Cornwell, P. and Barry, B. W. (1994). Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-flurouracil. Journal of Pharmacy and Pharmacology, 46(4): 261-269.
Hirvonen, J. H., Rytting, R. N., Paronen, P., and Urtti, A. (1991). Dodecyl N, N-demethylamino acetate and cc enhance drug penetration across human, snake and rabbit skin. Pharmaceutical Research, 8(7): 933-937.
Kantor, T. G. (1986). Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy, 6(3): 93-103.
Knutson, K., Potts, R. O., Guzek, D. B., Golden, G. M., Mckie, J. E., Lambert, W. J., and Higuchi, W. I. (1985). Macro and molecular physical-chemical consideration in understanding drug transport in stratum corneum. Journal of Controlled Release, 2: 67-87.
Koyama, Y. (1994). Comparative analysis of percutaneous absorption enhancement by D-limonene and oleic acid based on a skin diffusion model. Pharmaceutical Research, 11: 377-383
Lopez, A., Llinares, C., Cortell, C., and Herraez, M. (2000). Comparative enhancer effect 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.
Martin, A. (1993). Diffusion and dissolution. In Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences (Martin, A., ed.), pp. 877-898. Lea & Febiger, Philadelphia.
Moghimi, H., Williams, A. C., and Barry, B. W. (1996). A lamellar matrix model for stratum corneum intercellular lipids. IV: Effects of terpene penetration enhancers of 5-fluoouracil and oestradiol through the matrix. International Journal of Pharmaceutics, 145(1-2): 49-59.
Moghimi, H., Williams, A. C., and Barry, B. W. (1997). A lamellar matrix for stratum corneum intercellular lipids. V: Effects of terpene penetration enhancers on the structure and therrmal behavior of the matrix. International Journal of Pharmaceutics, 146(1): 41-54.
Moghimi, H. R., Williams, A. C., and Barry, B. W. (1998). Enhancement by terpenes of 5-fluorouracil permeation through the stratum corneum: model solvent approach Journal of Pharmacy and Pharmacology, 50: 955-964.
Narishetty, S. T. and Panchagnula, R. (2004). Transdermal delivery of zidovudine: Effect of terpenes and their mechanism of action. Journal of Controlled Release, 95(3): 367-379.
Ngawhirunpat, T., Opanasopit, P., Rojanarata, T.,Panomsuk, S., and Chanchome, L. (2008). Evaluation of simultaneous permeation and metabolism of methyl nicotinate in human, snake, and shed snake skin. Pharmaceutical Development and Technolology, 13(1): 75-83.
Nokhodchi, A., Sharabiani, K., Rashidi, M. R., and Ghafourian, T. (2007). The effect of terpene concentrations on the skin penetration of diclofenac sodium. Journal of Pharmaceutical Sciences, 335(1-2): 97-105.
Obata, Y. T. (1991). Combined effect of cyclic monoterpenes and ethanol on percutaneous absorption of diclofenac sodium. Drug Design and Delivery, 8(2): 137-144.
OECD (2000). Skin Absorption: In Vitro Method. OECD New Guideline Proposal on in vitro Percutaneous Absorption of Chemicals. Test Guideline 428, Paris.
Okabe, H., Obata, Y., Takayama, K., and Nagai, T. (1990). Percutaneous absorption enhancing and skin irritation of monoterpenes. Drug Design and Delivery, 6(3): 229-238.
Ogiso, T., Paku, T., Iwaki, M., and Tanino, T. (1995). Percutaneous penetration of fluorescein isothiocyanate-dextrans and the mechanism for enhancement effect of enhancers on the intercellular penetration. Biological and Pharmaceutical Bulletin, 18(11): 1566-71.
Songkro, S., Rades, T., and Becket, G. (2009). Effects of some terpenes on the in vitro permeation of LHRH through newborn pig skin. Die Pharmazie, 64(2): 110-5.
Takahashi, K., Tamagawa, S., Katagi. T., Rytting. H., Nishihata, T., and Mizuno, N. (1993). Percutaneous absorption of basic compounds through shed snake skin as model membrane. Journal of Pharmacy and Pharmacology, 4: 882-886.
Thomas, N. S. and Panchagnula, R. (2003). Transdermal delivery of zidovudine: Effect of vehicles on the permeation across rat skin and their mechanism of action. European Journal of Pharmaceutical Sciences, 18: 71-79
Vaddi, H. K. (2002). 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.
William, A. C. and Barry, B. W. (1991). Terpenes and the lipid-protein partitioning theory of skin penetration enhancement. Pharmaceutical Research, 8(1):17-24.
William, A. C. and Barry, B. W. (2004). Penetrationsenhancers. Advanced Drug Delivery Reviews, 56(5): 603-618.
Yamane, M. A., William, A. C., and Barry, B. W. (1995). The effect of terpenes and oleic acid as skin penetration enhancers toward 5-fluorouracil as assessed with time; permeation, partitioning and differential scanning calorimetry. International Journal of Pharmaceutics, 116 (2): 237-251.
Zhao, K. and Singh, J. (1998). Mechanisms of percutaneous absorption of tamaxifen by terpenes: eugenol, d-limonene and menthone. Journal of Controlled Release, 55(2-3): 253-260.
Zhao, K. and Singh, J. (2000). Mechanism(s) of in vitro percutaneous absorption enhancement of tamoxifen by enhancers. Journal of Pharmaceutical Sciences, 89(6): 771-80.
Barry, B. W. (1987). Mode of action of penetration enhancers in human skin. Journal of Controlled Release, 6: 85-97.
Bergstrom, K., Bergstrom, T., Knustson, K., Denoble,L.J., and Goates, C. Y. (1990). Percutaneous absorption enhancement of a ionic molecule by ethanol-water systems in human skin. Pharmaceutical Research, 7: 762-766.
Borras-Blasco, J., Lopez, A., Morant, M. J., Diez-Sales, O., and Herraez-Dominguez, M. (1996). Influence of sodium lauryl sulphate on the in vitro percutaneous absorption of compound with different lipophilicity. European Journal of Pharmaceutical Sciences, 5: 15-22.
Borras-Blasco, J., Diez-Sales, O., Lopez, A., and Herraez-Dominguez, M. (2004). A mathematical approach to predicting the percutaneous absorption enhancing effect of sodium lauryl sulphate. International Journal of Pharmaceutics, 269: 121-129.
Knutson, K., Potts, R. O., Guzek, D. B., Golden, G. M., Mckie, J. E., Lambert, W. J., and Higuchi W. I. (1985). Macro and molecular physical-chemical consideration in understanding drug transport in stratum corneum. Journal of Controlled Release, 2: 67-87.
Cornwell, P. and Barry, B. W. (1994). Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-flurouracil. Journal of Pharmacy and Pharmacology, 46(4): 261-269.
Hirvonen, J. H., Rytting, R. N., Paronen, P., and Urtti, A. (1991). Dodecyl N, N-demethylamino acetate and cc enhance drug penetration across human, snake and rabbit skin. Pharmaceutical Research, 8(7): 933-937.
Kantor, T. G. (1986). Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy, 6(3): 93-103.
Knutson, K., Potts, R. O., Guzek, D. B., Golden, G. M., Mckie, J. E., Lambert, W. J., and Higuchi, W. I. (1985). Macro and molecular physical-chemical consideration in understanding drug transport in stratum corneum. Journal of Controlled Release, 2: 67-87.
Koyama, Y. (1994). Comparative analysis of percutaneous absorption enhancement by D-limonene and oleic acid based on a skin diffusion model. Pharmaceutical Research, 11: 377-383
Lopez, A., Llinares, C., Cortell, C., and Herraez, M. (2000). Comparative enhancer effect 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.
Martin, A. (1993). Diffusion and dissolution. In Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences (Martin, A., ed.), pp. 877-898. Lea & Febiger, Philadelphia.
Moghimi, H., Williams, A. C., and Barry, B. W. (1996). A lamellar matrix model for stratum corneum intercellular lipids. IV: Effects of terpene penetration enhancers of 5-fluoouracil and oestradiol through the matrix. International Journal of Pharmaceutics, 145(1-2): 49-59.
Moghimi, H., Williams, A. C., and Barry, B. W. (1997). A lamellar matrix for stratum corneum intercellular lipids. V: Effects of terpene penetration enhancers on the structure and therrmal behavior of the matrix. International Journal of Pharmaceutics, 146(1): 41-54.
Moghimi, H. R., Williams, A. C., and Barry, B. W. (1998). Enhancement by terpenes of 5-fluorouracil permeation through the stratum corneum: model solvent approach Journal of Pharmacy and Pharmacology, 50: 955-964.
Narishetty, S. T. and Panchagnula, R. (2004). Transdermal delivery of zidovudine: Effect of terpenes and their mechanism of action. Journal of Controlled Release, 95(3): 367-379.
Ngawhirunpat, T., Opanasopit, P., Rojanarata, T.,Panomsuk, S., and Chanchome, L. (2008). Evaluation of simultaneous permeation and metabolism of methyl nicotinate in human, snake, and shed snake skin. Pharmaceutical Development and Technolology, 13(1): 75-83.
Nokhodchi, A., Sharabiani, K., Rashidi, M. R., and Ghafourian, T. (2007). The effect of terpene concentrations on the skin penetration of diclofenac sodium. Journal of Pharmaceutical Sciences, 335(1-2): 97-105.
Obata, Y. T. (1991). Combined effect of cyclic monoterpenes and ethanol on percutaneous absorption of diclofenac sodium. Drug Design and Delivery, 8(2): 137-144.
OECD (2000). Skin Absorption: In Vitro Method. OECD New Guideline Proposal on in vitro Percutaneous Absorption of Chemicals. Test Guideline 428, Paris.
Okabe, H., Obata, Y., Takayama, K., and Nagai, T. (1990). Percutaneous absorption enhancing and skin irritation of monoterpenes. Drug Design and Delivery, 6(3): 229-238.
Ogiso, T., Paku, T., Iwaki, M., and Tanino, T. (1995). Percutaneous penetration of fluorescein isothiocyanate-dextrans and the mechanism for enhancement effect of enhancers on the intercellular penetration. Biological and Pharmaceutical Bulletin, 18(11): 1566-71.
Songkro, S., Rades, T., and Becket, G. (2009). Effects of some terpenes on the in vitro permeation of LHRH through newborn pig skin. Die Pharmazie, 64(2): 110-5.
Takahashi, K., Tamagawa, S., Katagi. T., Rytting. H., Nishihata, T., and Mizuno, N. (1993). Percutaneous absorption of basic compounds through shed snake skin as model membrane. Journal of Pharmacy and Pharmacology, 4: 882-886.
Thomas, N. S. and Panchagnula, R. (2003). Transdermal delivery of zidovudine: Effect of vehicles on the permeation across rat skin and their mechanism of action. European Journal of Pharmaceutical Sciences, 18: 71-79
Vaddi, H. K. (2002). 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.
William, A. C. and Barry, B. W. (1991). Terpenes and the lipid-protein partitioning theory of skin penetration enhancement. Pharmaceutical Research, 8(1):17-24.
William, A. C. and Barry, B. W. (2004). Penetrationsenhancers. Advanced Drug Delivery Reviews, 56(5): 603-618.
Yamane, M. A., William, A. C., and Barry, B. W. (1995). The effect of terpenes and oleic acid as skin penetration enhancers toward 5-fluorouracil as assessed with time; permeation, partitioning and differential scanning calorimetry. International Journal of Pharmaceutics, 116 (2): 237-251.
Zhao, K. and Singh, J. (1998). Mechanisms of percutaneous absorption of tamaxifen by terpenes: eugenol, d-limonene and menthone. Journal of Controlled Release, 55(2-3): 253-260.
Zhao, K. and Singh, J. (2000). Mechanism(s) of in vitro percutaneous absorption enhancement of tamoxifen by enhancers. Journal of Pharmaceutical Sciences, 89(6): 771-80.