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Research Article

Calculation procedures and HPLC method for analysis of the lipophilicity of acyclovir esters

, &
Pages 663-669 | Received 12 Nov 2013, Accepted 03 Feb 2014, Published online: 03 Mar 2014
 

Abstract

Acyclovir (ACV) belongs to a class of drugs with low bioavailability. Selected ACV esters including acetyl (Ac-), isobutyryl (iBut-), pivaloyl (Piv-), ethoxycarbonyl (Etc-) and nicotinoyl (Nic-) were synthesized, and their lipophilicity was determined by the high-performance liquid chromatography (HPLC) RP method. Statistical analyses of the comparative values of log P and clog P were carried out using computational methods. It was proved that the AC log P algorithm can be useful for the analysis of these compounds and has a statistically justified application in the assessment of the quantitative structure–activity relationship. Moreover, the lipophilicity determined by the HPLC method appears as follows: ACV < Ac- < Nic- < Etc- < iBut- < Piv-.

Acknowledgements

The authors would like to thank DSc Tomasz Goslinski for assistance and access to the laboratory facilities at the Department of Chemical Technology of Drugs, Poznan University of Medical Sciences.

Declaration of interest

The authors report no conflicts of interest.

This study was partly supported by UMP grant No 502-14-03305411-99674 and the European Fund for Regional Development No UDA-POIG.02.01.00-30-182/09.

Notice of Correction:

The authors have updated the figure caption for Figure 3 and added three lines in Table 3 since the first online publication of this article.

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