Correlation between n-octanol/water partition coefficient and liquid chromatographic retention for caffeine and its metabolites, and some structure-pharmacokinetic considerations

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Abstract
A method to establish the correlation between the reverse phase high performance liquid chromatographic retention of caffeine and its metabolites and their n‐octanol/water partition coefficients is described. The log (P) values were always below zero, ranging from −0.02 to −2.03. The capacity factor quadratically back‐extrapolated to 100% water eluent (k'w) was used as the index of lipophilicity. The compounds examined gave a good correlation (r > 0.99) with log (k'w) if considered in separate series, depending on the substituent position. For a structure‐pharmacokinetic relationship study, correlations were found between the partition coefficient and some pharmacokinetic parameters, suggesting that for drugs that are widely metabolized, any predictions of their disposition from physicochemical characteristics are hazardous.