The enantioselective extraction of hydrophobic pranoprofen (PRA) enantiomers by hydrophilic beta-cyclodextrin (beta-CD) selectors was studied in a batch system. The influence of process variables, including types of organic solvents and beta-CD derivatives, the concentration of the selector, pH, and temperature, on the extraction efficiency was studied. A reactive extraction model with a homogeneous aqueous phase reaction of R,S-PRA with Me-beta-CD (methyl-beta-cyclodextrin) was established to describe the experimental data, and important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic PRA were 0.031 and 25.304, respectively. The equilibrium constants of the complexation reactions were (367 and 269) L.mol(-1) for R- and S-PRA, respectively. With the experimental and modeled data, the optimum conditions were obtained at a pH of 3.5 and a Me-beta-CD concentration of 0.1 mol.kg(-1) with an optimum performance factor (pf) of 0.039. The model was verified experimentally with excellent results.