PMID: 11920772Mar 29, 2002Paper

Thermodynamic origin of the solubility profile of drugs showing one or two maxima against the polarity of aqueous and nonaqueous mixtures: niflumic acid and caffeine

Journal of Pharmaceutical Sciences
P BustamanteB Escalera

Abstract

The purpose of this work was to investigate the origin of the different solubility profiles of drugs against the polarity of solvent mixtures with a common cosolvent. Niflumic acid and caffeine where chosen as model drugs. The solubilities were measured at five or six temperatures in aqueous (ethanol-water) and nonaqueous (ethyl acetate-ethanol) mixtures. The enthalpies of solution were obtained at the harmonic mean of the experimental temperature. Solid phase changes were analyzed using differential scanning calorimetry and thermomicroscopy. A single solubility maximum was obtained for niflumic acid against the solubility parameter of both mixtures that is not related to solid phase changes. In contrast, caffeine displays two maxima and anhydrous-hydrate transition occurs at the solubility peak in the amphiprotic mixture. The apparent enthalpies of solution of both drugs show endothermic maxima against solvent composition that are related to hydrophobic hydration. A general explanation for the cosolvent action in aqueous mixtures is proposed. The dominant mechanism shifts from entropy to enthalpy at a certain cosolvent ratio dependent on the hydrophobicity and the solubility parameter of the drug. Niflumic acid and caffeine sh...Continue Reading

References

Jun 1, 1980·Journal of Pharmaceutical Sciences·A AdjeiA Martin
Mar 1, 1994·The Journal of Pharmacy and Pharmacology·J B EscaleraA Martin
Oct 1, 1996·Journal of Pharmaceutical Sciences·C Bustamante, P Bustamante
Apr 17, 1999·International Journal of Pharmaceutics·S RomeroP Bustamante
Mar 8, 2000·Chemical & Pharmaceutical Bulletin·A Jouyban-GharamalekiB J Clark
Aug 1, 1963·Journal of Pharmaceutical Sciences·E SHEFTER, T HIGUCHI

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Citations

May 13, 2010·Chemical & Pharmaceutical Bulletin·Pilar BustamanteAngeles Peña
Sep 1, 2008·Indian Journal of Pharmaceutical Sciences·Mahua SarkarR Panchagnula
Aug 31, 2007·Drug Development and Industrial Pharmacy·Subrata MallickPintu K De
Apr 7, 2010·International Journal of Pharmaceutics·Yasuhiro MiyakoRodolfo Pinal
Jan 6, 2007·International Journal of Pharmaceutics·Monica DiasMajella E Lane
May 26, 2015·International Journal of Pharmaceutics·Lin Luo, Majella E Lane
Jan 13, 2006·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Kohsaku KawakamiYasuo Ida
Jun 15, 2004·Journal of Pharmaceutical and Biomedical Analysis·Susana RomeroMarzia Cirri
May 5, 2004·Journal of Pharmaceutical Sciences·Kohsaku KawakamiYasuo Ida
Dec 11, 2007·Soft Matter·Richard HoogenboomUlrich S Schubert
Oct 5, 2019·Pharmaceutics·Chin-Ping KungRenée McCulloch
Jan 1, 2019·Crystal Growth & Design·Víctor R Vázquez MarreroVilmalí López-Mejías

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