A supported liquid membrane (SLM) containing the chiral selector N-hexadecyl-L-hydroxyproline (HHP) was characterized for the enantioseparation of a beta-blocking drug. SR-propranolol was the target racentic mixture to be resolved by the membrane separation system. The different affinity shown by the selected carrier, HHP, for the two propranolol enantiomers produced a discrimination of their transport through this SLM. We investigated the influence of various chemical parameters involved in that system, such as the acidity of feed and receiving phases, as well as the carrier concentration in the membrane. Valuable knowledge on the transport mechanisms within this system was thus attained.