Synthesis and investigation of urea compounds as transdermal penetration enhancers

International Journal of Pharmaceutics

Volumn 167, Issue 1-2, 1998, Pages 165-175

  Godwin, Donald A ^a   Player, Mark R ^b   Sowell, J Walter ^c   Michniak, Bozena B ^c  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b Laboratory of Medicinal Chemistry   (United States)

^c Dept of Basic Pharmaceutical Sci Coll of Pharm Univ of S C   (United States)

Author keywords

Hairless mouse; Hydrocortisone; Percutaneous penetration; Skin retention; Transdermal drug delivery; Ureas

Indexed keywords

HYDROCORTISONE; PROPYLENE GLYCOL; THIOUREA DERIVATIVE; UREA DERIVATIVE;

ARTICLE; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG PENETRATION; KINETICS; PRIORITY JOURNAL; SKIN PENETRATION; SKIN PERMEABILITY; STRUCTURE ACTIVITY RELATION; TRANSDERMAL DRUG ADMINISTRATION; UREA CYCLE;

EID: 0032102804     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(98)00060-X     Document Type: Article

References (34)

1. Barry, B.W., 1983. Percutaneous Absorption. Marcel Dekker, New York, pp. 127-280.
2. Barry, B.W., 1987. In: Barry, B.W., Shroot, B., Schaefer, H. (Eds.), Skin Pharmacokinetics. Karger, Basel, Switzerland, pp. 121-137.
3. Barry B.W. Modern methods of promoting drug absorption through the skin. Mol. Aspects Med. 12:1991;195-241.
4. Barry B.W., Bennett S.L. Effect of penetration enhancers on the permeation of mannitol, hydrocortisone and progesterone through human skin. J. Pharm. Pharmacol. 39:1987;535-546.
5. Barry B.W., Woodford R. Proprietary hydrocortisone creams: vasoconstrictor activities and bio-availabilities of six preparations. Br. J. Dermatol. 95:1976;423-425.
6. Beastall J. The influence of urea on percutaneous absorption. Pharm. Res. 3:1986;268-274.
7. Chien, Y.W., 1982. Novel Drug Delivery Systems: Fundamentals, Developmental Concepts, Biomedical Assessments. Marcel Dekker, New York, p. 551.
8. Erickson J.G. Reactions of long-chain amines, II: reactions with urea. J. Am. Chem. Soc. 76:1954;3977-3978.
9. Erickson J.G. Reactions of long-chain amines, VI: preparations of thioureas. J. Org. Chem. 21:1956;483-485.
10. Feldman R., Maibach H. Percutaneous penetration of hydrocortisone with urea. Arch. Dermatol. 109:1974;58-59.
11. Gunnar, A.R. (Ed.), 1995. Remington's Pharmaceutical Sciences. 19th ed. Mack Publishing, Easton, PA.
12. Hoskins W.M., Bloxham H.P., Vaness M.W. The insecticidal effects of organic compounds. J. Econ. Entomol. 33:1940;875-881.
13. Kim C.K., Kim J.J., Chi S.C., Shim C.K. Effect of fatty acids and urea on the penetration of ketoprofen through rat skin. Int. J. Pharm. 99:1993;109-118.
14. Lippold B.C., Hackemuller D. The influence of skin moisturizers on drug penetration in vivo. Int. J. Pharm. 61:1990;205-211.
15. Michniak B.B., Player M.R., Chapman J.M., Sowell J.W. In vitro evaluation of a series of Azone analogs as dermal penetration enhancers. Int. J. Pharm. 91:1993;85-93.
16. Michniak B.B., Player M.R., Fuhrman L.C., Christensen C.A., Chapman J.M., Sowell J.W. In vitro evaluation of a series of Azone analogs as dermal penetration enhancers II: (Thio)amides. Int. J. Pharm. 94:1993;203-210.
17. Michniak, B.B., Player, M.R., Chapman, J.M., Sowell, J.W., Brain, K.R., James, V.J., Walters, K.A. (Eds.), 1993c. Prediction of Percutaneous Penetration: Methods, Measurement and Modelling. STS Publishing, Cardiff, UK, p. 277-286.
18. Michniak B.B., Player M.R., Fuhrman L.C. Jr., Christensen C.A., Chapman J.M., Sowell J.W. In vitro evaluation of a series of Azone analogs as dermal penetration enhancers, III: acyclic amides. Int. J. Pharm. 110:1994;231-239.
19. Michniak B.B., Player M.R., Chapman J.M., Sowell J.W. Azone analogs as permeation enhancers: effect of different vehicles on hydrocortisone acetate skin permeation and retention. J. Cont. Release. 32:1994;147-154.
20. Michniak B.B., Player M.R., Godwin D.A., Phillips C.A., Sowell J.W. In vitro evaluation of a series of Azone analogs as dermal penetration enhancers, IV: amines. Int. J. Pharm. 116:1995;201-209.
21. Niazy E.M. Influence of oleic acid and other permeation promoters on transdermal delivery of dihydroergotamine through rabbit skin. Int. J. Pharm. 67:1991;97-100.
22. Nishihata T., Rytting J.H., Kamada A., Matsumoto K., Takahashi K. Combined effect of alcohol and urea on the in vitro transport of indomethacin across rat dorsal skin. J. Pharm. Sci. 79:1990;487-489.
23. Phillips, C.A., 1995. Efficacy and Potential Toxicity of Novel Penetration Enhancers, University of South Carolina, Dissertation.
24. Raab W. Biochemistry, pharmacology and toxicology of urea. Hautarzt. 40:1989;23-26.
25. Ranade V.V. Drug delivery systems, 6: transdermal drug delivery. J. Clin. Pharmacol. 31:1991;401-418.
26. Ritschel, W.A., Sprockel, O.L., 1988. Sorption promoters for topically applied substances. Drugs of Today, 24 613-628.
27. Sasaki H., Kojima M., Nakamura J., Shibasaki J. Enhancing effect of pyrrolidone derivatives on transdermal penetration of phenolsulfonphthalein and indomethacin from aqueous vehicle. Chem. Pharm. Bull. 38:1990;797-799.
28. Sasaki H., Kojima M., Mori Y., Nakamura J., Shibasaki J. Enhancing effect of pyrrolidone derivatives on transdermal penetration of 5-fluorouracil, triamcinolone acetonide, indomethacin, and flurbiprofen. J. Pharm. Sci. 80:1991;533-538.
29. Sheard C., Roth G.M., Horton B.T. Relationships between accommodation and convergence and their clinical significance. Arch. Phys. Therap. 20:1939;133-136.
30. 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 bioavaliability and bioequivalence. Pharm. Res. 4:1987;265-267.
31. Sloan K.B., Beall H.D., Weinar W.R., Villanueva R. The effect of receptor composition on the permeability of hairless mouse skin in diffusion cell experiments. Int. J. Pharm. 72:1991;97-104.
32. Vishnyakova T.P., Golubeva I.A., Glebova E.V. Substituted ureas, synthetic methods and applications. Usp. Khim. 54:1985;429-449.
33. Williams A.C., Barry B.W. Urea analogs in propylene glycol as penetration enhancers in human skin. Int. J. Pharm. 56:1989;43-50.
34. Wohlrab W. The influence of urea on the penetration kinetics of topically applied corticosteroids. Acta Dermato-Vener. 64:1984;233-238.