Influence of Drug Lipophilicity on Terpenes as Transdermal Penetration Enhancers

REFERENCES

• Barry B. W. Percutaneous absorption, in Dermatological Formulations. Marcel Dekker, , New York 1983; 127–280
   Google Scholar
• Barry B. W., Bennett S. L. Effect of penetration enhancers on the permeation of mannitol, hydrocortisone and progesterone through human skin. J. Pharm. Pharmacol. 1987; 39: 535–546
   PubMed Web of Science ®Google Scholar
• Aungst B. J., Rogers N. J., Shefter E. Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides, and amides. Int. J. Pharm. 1986; 33: 225–229
   Web of Science ®Google Scholar
• Bhatt P. P., Rytting J. H., Topp E. M. Influence of azone and lauryl alcohol on the transport of acetaminophen and ibuprofen through shed snake skin. Int. J. Pharm. 1991; 72: 219–226
   Web of Science ®Google Scholar
• Elfbaum S. G., Laden K. The effect of dimethyl-sulfoxide on percutaneous absorption: a mechanistic study. J. Cutaneous Pathol. 1968; 11: 259–264
   Google Scholar
• Francoeur M. L., Golden G. M., Potts R. O. Oleic acid: its effects on stratum corneum in relation to (trans)dermal drug delivery [Continuous effect of azone pretreatment on permeability of antivirotic Ara-ADA through hairless mouse skin]. Pharm. Res. 1989; 24: 290–294
   Google Scholar
• Skelly J., Shah V., Maibach H., Guy R., Flynn G., Yacobi A. FDA and AAPS report of the workshop on principles and practices of in vitro percutaneous penetration studies: relevance to bioavailability and bioequivalence. Pharm. Res. 1987; 4: 265–267
   Web of Science ®Google Scholar
• Ranade V. V. Drug delivery systems. 6. Transdermal drug delivery [Review]. J. Clin. Pharmacol. 1991; 31: 401–418
   PubMed Web of Science ®Google Scholar
• Hashida M., Yamashita F. Terpenes as penetration enhancers, in Percutaneous Penetration Enhancers, E. W. Smith, H. I. Maibach. CRC Press, Boca Raton, FL 1995; 309–321
   Google Scholar
• Arellano A., Sontoya S., Martin C., Ygartua P. Enhancing effect of terpenes on the in vitro percutaneous absorption of diclofenac sodium. Int. J. Pharm. 1996; 130: 141–145
   Web of Science ®Google Scholar
• Okabe H., Takayama K., Nagai T. Percutaneous absorption of ketoprofen from acrylic gel patches containing d-limonene and ethanol as absorption enhancers. Chem. Pharm. Bull. 1992; 40: 1906–1910
   PubMed Web of Science ®Google Scholar
• Miyazaki S., Tobiyama T., Takada M., Attwood D. Percutaneous absorption of indomethacin from pluronic F127 gels in rats. J. Pharm. Pharmacol. 1995; 47: 455–457
   PubMed Web of Science ®Google Scholar
• Yamane M. A., Williams A. C., Barry B. W. Effects of terpenes and oleic acid as skin penetration enhancers toward 5-fluorouracil as assessed with time: permeation, partitioning and differential scanning calorimetry. Int. J. Pharm. 1995; 116: 237–251
   Web of Science ®Google Scholar
• Williams A. C., Barry B. W. Terpenes and the lipid-protein-partitioning theory of skin penetration enhancement. Pharm. Res. 1991; 8: 17–24
   PubMed Web of Science ®Google Scholar
• Center for Food Safety and Applied Nutrition, Everything Added to Food in the United States: A Food Additive Database. Food and Drug Administration, Rockville, MD May 28, 1998
   Google Scholar
• Williams A. C., Barry B. W. The enhancement index concept applied to terpene penetration enhancers for human skin and model lipophilic (oestradiol) and hydrophilic (5-fluorouracil) drugs. Int. J. Pharm. 1991; 74: 157–168
   Web of Science ®Google Scholar
• Cornwell P. A., Barry B. W., Bouwstra J. A., Gooris G. S. Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. Int. J. Pharm. 1996; 127: 9–26
   Web of Science ®Google Scholar
• Michniak B. B., Player M. R., Chapman J. M., Jr., Sowell J. W., Sr. Optimization of dermal delivery using azone analogs as enhancers, Proc. 12th Pharm. Technol. Conf. 1993; 2: 158–273
   Google Scholar
• Chien Y. W. Novel Drug Delivery Systems: Fundamentals, Developmental Concepts, Biomedical Assessments. Marcel Dekker, , New York 1982
   Google Scholar
• Phillips C. A., Michniak B. B. Transdermal delivery of drugs with differing lipophilicities using azone analogs as dermal penetration enhancers. J. Pharm. Sci. 1995; 84: 1427–1433
   PubMed Web of Science ®Google Scholar
• Obata Y., Takayama K., Maitani Y., Machida Y., Nagai T. Effect of pretreatment of skin with cyclic monoterpenes on permeation of diclofenac in hairless rat. Biol. Pharm. Bull. 1993; 16: 312–314
   PubMed Web of Science ®Google Scholar
• Gao S., Singh J. Mechanism of transdermal transport of 5-fluorouracil by terpenes: carvone, 1.8-cineole, and thymol. Int. J. Pharm. 1997; 154: 67–77
   Web of Science ®Google Scholar
• Cornwell P. A., Barry B. W. Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil. J. Pharm. Pharmacol. 1994; 46: 261–269
   PubMed Web of Science ®Google Scholar
• Kararli T., Kirchhoff C., Penzotti S. Enhancement of transdermal transport of azidothymidine (AZT) with novel terpene and terpene-like enhancers: in vivo–in vitro correlations. J. Controlled Release 1995; 34: 43–51
   Web of Science ®Google Scholar
• Kunta J. R., Goskonda V. R., Brotherton H. O., Khan M. A., Reddy I. K. Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. J. Pharm. Sci. 1997; 86: 1369–1373
   PubMed Web of Science ®Google Scholar
• Advanced Chemistry Development, ACD/Labs™. TorontoCanada 1995
   Google Scholar
• Kitagawa S., Hosokai A., Aseda Y., Yamamoto N., Aneko Y., Matsuoka E. Permeability of benzoic acid derivatives in excised guinea pig dorsal skin and the effects of L-menthol. Int. J. Pharm. 1998; 161: 115–122
   Google Scholar
• Koyama Y., Bando H., Yamashita F., Takakura Y., Sezaki H., Hashida M. Comparative analysis of percutaneous absorption enhancement by d-limonene and oleic acid based on a skin diffusion model. Pharm. Res. 1994; 11: 377–383
   PubMed Web of Science ®Google Scholar
• Kikuchi K., Takayama K., Nagai T. Effect of d-limonene on the amounts of ethanol and indomethacin penetrated from aqueous gel ointments to rat skin. Chem. Pharm. Bull. 1992; 40: 3108–3109
   PubMed Web of Science ®Google Scholar
• Kaplun-Frischoff Y., Touitou E. Testosterone skin permeation enhancement by menthol through formation of eutectic with drug and interaction with skin lipids. J. Pharm. Sci. 1997; 86: 1394–1399
   PubMed Web of Science ®Google Scholar
• Gao S., Singh P. In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes. J. Controlled Release 1998; 51: 193–199
   PubMed Web of Science ®Google Scholar