Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Solution thermodynamics of indomethacin in propylene glycol + water mixtures

Holguin, A. R.[Andres R], Rodriguez, G. A., Cristancho, D. M.[Diana M.], Delgado, D. R.[Daniel R.], Martinez, F.[Fleming]
Fluid Phase Equilib. 2012, 314, 134-139
ABSTRACT
The equilibrium solubilities of the analgesic drug indomethacin (IMC) in propylene glycol + water binary mixtures were determined at several temperatures from 293.15 to 313.15 K. The Gibbs energy, enthalpy, and entropy of solution and of mixing were obtained from these solubility data. The solubility was maximal in neat propylene glycol and very low in pure water at all the temperatures studied. A non-linear plot of enthalpy of solution vs. Gibbs energy of solution with negative slope from pure water up to 0.80 in mass fraction of propylene glycol and positive beyond this composition up to neat propylene glycol was obtained at the mean temperature, 303.15 K. This behavior is similar to those reported in the literature for this drug in 1,4-dioxane + water and ethanol + water mixtures. Accordingly, the driving mechanism for IMC solubility in the water-rich mixtures was the entropy, probably due to water-structure loss around non-polar moieties of the drug and for the propylene glycol-rich mixtures it was the enthalpy, probably due to its better solvation of the drug.
Compounds
# Formula Name
1 C19H16ClNO4 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid
2 C3H8O2 1,2-propanediol
3 H2O water
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • 2
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Spectrophotometry
  • 65