Biological and Pharmaceutical Bulletin
Online ISSN : 1347-5215
Print ISSN : 0918-6158
ISSN-L : 0918-6158
Enhanced in Vitro Percutaneous Penetration of Salicylate by Ion Pair Formation with Alkylamines
Masanori KADONOKazuyoshi KUBOHirohisa MIYAZAKINobuteru TOJYOShinsaku NAKAGAWAKazuyuki MIYASHITATakeshi IMANISHIJ. Howard RYTTINGTadanori MAYUMI
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1998 Volume 21 Issue 6 Pages 599-603


The apparent octanol/water partition coefficient (APC) of salicylate (SA) increased as the concentration of alkylamine (amyl, hexyl, heptyl, octyl and nonylamine) in aqueous phase increased, presumably through intermolecular ion pair formation between the negatively charged SA moiety and the alkylamine cation. The true partition coefficient (TPC) and the formation constant (Kf) of the ion pair were calculated from the partition data. The skin permeability of SA increased as the APC of SA increased, when 20-fold molar excess of alkylamine was added to the donor compartment. Permeability of ion pairs (PAB) from the aqueous phase to a shed snake skin was estimated from the permeability data assuming 1 : 1 ion pair. The methylene group contribution to the free energy of transfer of ion pairs from water to the shed snake skin was less than the reported value for nonionized drugs. This suggests that the ion pair is more polar by nature than nonionized molecules, even if ionic characteristics are masked to some extent by ion pair formation.

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