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AAPS PharmSci. Mar 2004; 6(1): 22–30.
Published online Jan 26, 2004. doi:  10.1208/ps060103
PMCID: PMC2750938
Solvation and hydration characteristics of ibuprofen and acetylsalicylic acid
German L. Perlovich,1,2 Sergey V. Kurkov,2 Andrey N. Kinchin,2 and Annette Bauer-Brandlcorresponding author1
1Institute of Pharmacy, University of Tromsø, Breivika, N-9037 Tromsø, Norway
2Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russia
Annette Bauer-Brandl, Phone: 47 77646160, Fax: 47 77646151, annetteb/at/farmasi.uit.no.
corresponding authorCorresponding author.
Received September 24, 2003; Accepted November 30, 2003.
Ibuprofen and acetylsalicylic acid were studied by thermoanalytical methods: sublimation calorimetry, solution calorimetry, and with respect to solubility. Upon measuring the temperature dependences of the saturated vapor pressure, enthalpies of sublimation, ΔHsub0, as well as the entropies of sublimation, ΔHsub0, and their respective relative fractions in the total process were calculated. The Gibbs energy of solvation in aliphatic alcohols as well as the enthalpic and entropic fractions thereof were also studied and compared with the respective properties of model substances and other nonsteroidal antiinflammatory drugs (benzoic acid, diflunisal, flurbiprofen, ketoprofen, and naproxen). In all cases, enthalpy was found to be the driving force of the solvation process. Correlations were derived between Gibbs energy of solvation in octanol, ΔGsolvOct, and the transfer Gibbs energy from water to octanol, ΔGtr0. Influence of mutual octanol and water solubilities on the driving force of partitioning is discussed. An enthalpy-entropy-compensation effect in octanol was observed, and consequences of deviation from the general trend are also discussed.
Keywords: ibuprofen, acetylsalicylic acid, NSAID, sublimation, solvation, hydration, plasma half-life
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