Promoting Mechanism of Menthol Derivative, 1-O-Ethyl-3-buthylcyclohexanol, on the Percutaneous Absorption of Ketoprofen

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概要

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• Menthol derivatives were synthesized and evaluated for their promoting activity on the percutaneous absorption of ketoprofen and skin irritation in vivo, choosing O-ethylmenthol(MET)as the mother compound. The compound having a C-3 positionned n-butyl group(1-O-ethyl-3-n-butylcyclohexanol, OEBC)indicated the most promoting activity and caused relatively little skin irritation. In order to understand enhancement mechanism of OEBC an in vitro permeation study of ketoprofen was performed. The time course of the cumulative amounts of drug permeated through the rat skin exhibited a linear relation after an initial lag time. This was analyzed in membrane diffusion model and the diffusion and partition parameters of ketoprofen were estimated. Both parameters were remarkably enhanced when a hydrogel containing a small quantity of OEBC(0.5%)was applied. Furthermore, to clarify the site of action of OEBC, we also investigated in vitro permeation study of ketoprofen employing different skins of state, reversed skin and stratum corneum stripped skin. When OEBC was added to the hydrogels which were applied to the reversed and stripped skins, almost no changes of the flux were observed compared with the control(without OEBC). These results suggested that the site of action of OEBC was stratum corneum. Morphological changes of the stratum corneum surface were microscopically observed with 0-2% OEBC. The spaces between the stratum corneum cells treated with 0.5-2% OEBC became extended and the shape of each cell became clear. This may suggest that the site of action of OEBC was the intercellular of stratum corneum. Furthermore, an electron spin resonance study was performed to investigate the effect of OEBC on the intercellular lipid bilayer fluidity of the stratum corneum and the rotational correlation times were calculated. 2, 2, 6, 6-Tetramethylpiperidine-1-oxyl(TEMPO)and 4-hydroxy-2, 2, 6, 6-tetramethylpiperidine-1-oxyl(TEMPOL)were used as the spin label. In use of OEBC, the fluidity of TEMPO labeled the stratum corneum lipid increased as the addition of OEBC. The results suggested that OEBC promote the penetration of drugs by enhancing fluidity of the local lipid bilayers around TEMPO.

• 公益社団法人日本薬学会の論文
• 2001-09-01

著者

• YOSHIMURA Yoshihiro

  Department of Analytical Chemistry, Hoshi University

• Obata Yasuko

  Department of Pharmaceutics, Hoshi University

• Takayama Kozo

  Department of Pharmaceutics, Hoshi University

• Nagai T

  Department Of Pharmaceutics Hoshi University

• Obata Yasuko

  Department Of Pharmaceutics Hoshi University

• Takayama K

  Hoshi Univ. Tokyo Jpn

• Takayama Kozo

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hoshi University

• NAGAI TSUNEJI

  Department of Pharmaceutics, Hoshi University

• Yoshimura Y

  Department Of Analytical Chemistry Hoshi University

• Yoshimura Yoshihiro

  Department Of Analytical Chemistry Faculty Of Pharmaceutical Sciences Hoshi University

• Takayama Kozo

  Dep. Of Pharmaceutics Hoshi Univ.

• Li Chao

  Department Of Pharmaceutics Hoshi University

• Nagai Tsuneji

  Department Of Pharmaceutics Hoshi University

• HIGASHIYAMA Kimiko

  Department of Organic Chemistry, Hoshi University

• Li Chao

  Department Of Analytical Chemistry Shenyang Pharmaceutical University

• Higashiyama Kimiko

  Department Of Organic Chemistry Hoshi University

• Higashiyama Kimio

  Department Of Health Chemistry Faculty Of Pharmaceutical Sciences Hoshi University

• Takayama Kozo

  Department of Drug Delivery Research, Hoshi University

• Nagai Tsuneji

  Department of Drug Delivery Research, Hoshi University

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