Solvation and hydration characteristics of ibuprofen and acetylsalicylic acid.
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, DeltaH(0) (sub), as well as the entropies of sublimation, DeltaS(0) (sub), 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, DeltaG(Oct) (solv), and the transfer Gibbs energy from water to octanol, DeltaG(0) (tr). 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.
Perlovich
German L
GL
University of Tromsø, Institute of Pharmacy, Breivika, N-9037 Tromsø, Norway.
Kurkov
Sergey V
SV
Kinchin
Andrey N
AN
Bauer-Brandl
Annette
A
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000493:pharmacokinetics; D001241:Aspirin / Q000737:chemistry* / Q000493:pharmacokinetics; D004355:Drug Stability; D006207:Half-Life; D007052:Ibuprofen / Q000737:chemistry* / Q000493:pharmacokinetics; D012995:Solubility; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
D000894:Anti-Inflammatory Agents, Non-Steroidal; D014867:Water; D001241:Aspirin; D007052:Ibuprofen