title: Calculation procedures and HPLC method for analysis of the lipophilicity of acyclovir esters.
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-.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences , Poznan , Poland and.
authors.forename: Monika A
authors.initials: MA
authors.lastname: Lesniewska
authors.forename: Zofia
authors.initials: Z
authors.lastname: Gdaniec
authors.forename: Izabela
authors.initials: I
authors.lastname: Muszalska
mesh_terms: D000212:Acyclovir / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D000465:Algorithms; D000998:Antiviral Agents / Q000032:analysis / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D019295:Computational Biology; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D012015:Reference Standards; D012995:Solubility; D044366:Transition Temperature
chemical_list: D000998:Antiviral Agents; D000212:Acyclovir
keywords: Acyclovir; HPLC; antiviral; calculated log P; lipophilicity