Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Thermodynamic studies of drug - .alpha.-cyclodextrin interactions in water at 298.15 K: Procaine hydrochloride/lidocaine hydrochloride/tetracaine hydrochloride/ranitidine hydrochloride + .alpha.-cyclodextrin + H2O systems

Shaikh, V. R.[Vasim R.], Terdale, S. S.[Santosh S.], Hundiwale, D. G.[Dilip G.], Patil, K. J.[Kesharsingh J.]
J. Chem. Thermodyn. 2014, 68, 161-168
ABSTRACT
The osmotic coefficient measurements have been carried out for ternary aqueous solutions containing a fixed concentration of a-cyclodextrin (a-CD) of 0.1 mol kg 1 and varying the concentrations ( 0.012 to 0.21 mol kg 1) of drugs Procaine hydrochloride (PC HCl), Lidocaine hydrochloride (LC HCl), Tetracaine hydrochloride (TC HCl) and Ranitidine hydrochloride (RT HCl) at 298.15 K using vapour pressure osmometry. The water activities for each ternary system were measured and used to obtain the activity coefficients of a-cyclodextrin (a-CD) and drugs following the methodology developed by Robinson and Stokes for isopiestic measurements. The transfer Gibbs free energies of electrolyte (or drug) from water to an aqueous nonelectrolyte (a-CD) solutions (DGE tr) and that of nonelectrolyte (a-CD) from water to an aqueous electrolyte (or drug) solutions (DGN tr) have been calculated using the activity data. These were further used for the estimation of pair and triplet interaction parameters. By applying the method based on the application of the McMillan Mayer theory of virial coefficients to transfer free energy data, the salting constant (ks) values have been estimated at 298.15 K. The equilibrium constant (logK) values for the complexation due to host guest interaction are found high meaning encapsulation of drug molecules in a-CD cavities accompanied by pair-wise and triplet interaction due to hydrophobic hydration and interaction. The logK values are in the order of TC HCl greater than RT HCl greater than PC HCl greater than LC HCl. All these results are presented, compared and explained in light of host guest interaction concepts.
Compounds
# Formula Name
1 C36H60O30 .alpha.-cyclodextrin
2 C13H21ClN2O2 2-diethylaminoethyl p-aminobenzoate hydrochloride
3 C14H23ClN2O lidocaine hydrochloride
4 C15H25ClN2O2 2-(dimethylamino)ethyl 4-(butylamino)benzoate hydrochloride (1:1)
5 C13H23ClN4O3S ranitidine hydrochloride
6 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
  • 2
  • 6
  • 1
  • (Relative) activity - 6 ; Liquid
  • Molality, mol/kg - 2; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Molality, mol/kg - 1; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Vapor pressure osmometer
  • 8
  • POMD
  • 3
  • 6
  • 1
  • (Relative) activity - 6 ; Liquid
  • Molality, mol/kg - 3; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Molality, mol/kg - 1; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Vapor pressure osmometer
  • 9
  • POMD
  • 4
  • 6
  • 1
  • (Relative) activity - 6 ; Liquid
  • Molality, mol/kg - 4; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Molality, mol/kg - 1; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Vapor pressure osmometer
  • 8
  • POMD
  • 6
  • 1
  • 5
  • (Relative) activity - 6 ; Liquid
  • Molality, mol/kg - 5; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Molality, mol/kg - 1; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Vapor pressure osmometer
  • 8