Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Phase Equilibria of the System Drug + Water

Hassanein, A.[Adel], Hasse, M.[Martin], Enders, S.[Sabine]
J. Chem. Eng. Data 2011, 56, 4, 1356-1365
ABSTRACT
The production and the application of pharmaceuticals customarily involve liquid solvents for reaction, separation, and formulation. In pharmaceuticals, poor water solubility and slow dissolution into the gastrointestinal tract are major obstacles for releasing new dosage forms into the market. These issues have been responsible for the rejection of 70 % of the potentially active drugs. In this experimental study devoted to the phase behavior of three binary systems made from drug (S-(+)-2-(4-(2-methylpropyl) phenyl) propanoic acid [ibuprofen], (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol [farnesol], and ((R)-(6-methoxyquinolin-4-yl)((2S,4S,8(R)-8-vinylquinuclidin-2-yl)methanol [quinine]) and pure water. Beside the solubility in water (solid-liquid equilibrium, SLE), also the miscibility gaps (LLE) of two systems, namely (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol + water and (S)-2-(4-(2-methylpropyl)phenyl)propanoic acid + water, were measured applying the equilibrium method in combination with different analytical methods, like Karl Fischer titration, HPLC, and UV-vis spectroscopy. From the solubility data, the heat of fusion of the studied drugs could be extracted. An important factor which can have a significant impact on the thermodynamic data is the type of the investigated isomer.
Compounds
# Formula Name
1 C13H18O2 ibuprofen
2 C20H24N2O2 quinine
3 C15H26O 3,7,11-trimethyldodeca-2,6,10-trien-1-ol
4 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
  • 3
  • 4
  • Mass fraction - 3 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 7
  • POMD
  • 3
  • 4
  • Mass fraction - 4 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 8
  • POMD
  • 4
  • 1
  • Mass fraction - 4 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 5
  • POMD
  • 4
  • 1
  • Mass fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Titration method
  • 7
  • POMD
  • 4
  • 1
  • Mass fraction - 1 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 11
  • POMD
  • 2
  • 4
  • Mass fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • UV-VIS-spectroscopy
  • 6