A prodrug (Fig. 1(IV)) is synthesized consisting of the beta-blocker bupranolol which is covalently linked to 1, 3-dipalmitoyl-2-succinyl-glycerol. The resulting lipid-like prodrug is amphipathic and surface active. It disperses readily in H2O above 30 degrees C forming a smectic lamellar phase. This prodrug bears one positive charge at neutral pH and hence the swelling behaviour of dispersions in H2O is similar to that of charged phospholipids: the dispersions show continuous swelling with increasing water content and consequently in the excess H2O region of the phase diagram the thermodynamically most stable structure is the unilamellar vesicle. This includes oligomeric vesicles which may be defined as unilamellar vesicles containing smaller, also unilamellar vesicles entrapped in their internal aqueous compartment. The prodrug dispersions in H2O are polydisperse with vesicle sizes ranging from 0.1 micron to several micron. Sonication of these dispersions produce small unilamellar vesicles of an average size and size distribution similar to sonicated egg phosphatidylcholine dispersions. Unsonicated dispersions of the prodrug in H2O undergo reversibly sharp order-disorder transitions at 32 degrees C with an enthalpy change of delta H = 10 kcal/mol. In sonicated aqueous dispersions this phase transition is asymmetric and significantly broadened indicating that the cooperativity is markedly reduced. The peak temperature and enthalpy change of this broad transition are reduced compared to the transition observed with unsonicated dispersions. The temperature dependence of the electron spin resonance (ESR) hyperfine splitting and order parameter also reflects the order-disorder transition. From ESR spin labeling it is concluded that in sonicated dispersions the prodrug molecule is more mobile and its anisotropy of motion is reduced compared to unsonicated dispersions. This result indicates that the molecular packing in the highly curved bilayers of small unilamellar prodrug vesicles is significantly perturbed compared to bilayers of unsonicated dispersions.