Pressurized metered-dose inhalers (pMDIs) have been recognized as potential devices for the delivery of systemically acting drugs, including biomolecules, to and through the lungs. Therefore, the development of novel excipients capable of imparting stability to suspension formulations in hydrofluoroalkane (HFA) propellants is of great relevance because many of the drugs of interest are poorly soluble in HFAs. In this work, we use ab initio calculations and chemical force microscopy (CFM) to determine the HFA-philicity of the biodegradable and biocompatible ester moiety quantitatively. The complementary information obtained from the binding energy calculations and adhesion force measurements are used to gain microscopic insight into the relationship between the chemistry of the moiety of interest and its solvation in HFA. A lactide (LA)-based copolymer surfactant was synthesized and characterized, and its ability to stabilize a dispersion of micronized budesonide in HFA227 was demonstrated. These results corroborate the ab initio calculations and CFM and show that the LA-based moiety is a suitable candidate for enhancing the stability of dispersions in HFA-based pMDIs.