Correlations Between n-Octanol/Water Partition Coefficients and RP-HPLC Capacity Factors of 1,2-Dithiole-3-thiones and 1,2-Dithiol-3-ones

Abstract

From the experimental n-octanol/water partition coefficients (log Poct) of 33 1,2-dithiole-3-thiones and 18 1,2-dithiol-3-ones and their respective log k, Collander-type relationships were established at various volume fractions of methanol in the mobile phase and on an ODS 2 stationary phase. Collander-type relationships were also established between log Poct and log K0 (capacity factor extrapolated to 0% of organic modifier). The correlations are good, and their parameters depend on the volume fraction of organic modifier, as expected. These relationships were used to evaluate the log Poct of seven very lipophilic dithiolethiones (3.7 < log P < 7.2). Extrapolated values were compared with calculated values from fragmental constants determined in a previous work and with those given by Rekker.

log P Estimation of 1,2-Dithiole-3-thiones and 1,2-Dithiole-3-ones: A Comparison of Experimental and Calculative Approaches

“…Experimental log P data obtained in this study for derivatives 49Y68 are listed in the second column of Table II together with previously published data for compounds 01Y48 (12,13). For 10 compounds, experimental values were obtained by both HPLC and spectrophotometry; their close coincidence unequivocally proves the validity of the experimental results.…”

HPLC determination of anethole trithione and its application to pharmacokinetics in rabbits

“…free radicals, oxidants) [5,6]. Since ATT has very low intrinsic water solubility (0.0016 mM) [7,8], which results in some biopharmaceutical problems, it is necessary to increase the aqueous solubility of ATT and thus improve its bioavailability. A lot of new techniques and formulations have been investigated to enhance its bioavailability, such as complexation with ␤-cyclodextrins [9], solid dispersion with PEG [10].…”

Improvement in solubility and dissolution rate of 1,2‐dithiole‐3‐thiones upon complexation with β‐cyclodextrin and its hydroxypropyl and sulfobutyl ether‐7 derivatives

“…Since 1,2-dithiole-3-thiones are highly lipophilic compounds, [7][8] and since too high a lipophilicity can result in low permeability, 9 there is a need from a biopharmaceutical standpoint to increase the poor aqueous solubility of these nonionizable molecules (around 0.001 mg/mL) in order to circumvent the low and highly variable absorption generally seen with such products. 10 To reach that goal, we used cyclodextrins, since preliminary solubilization studies with cosolvents such as DMSO or PEG resulted in drug precipitation upon dilution.…”