Novel derivatives of cationic surfactant cetyltrimethylammonium bromide (CTAB) possessing anions of ibuprofen and naproxen as hydrophobic counterions were synthesized and characterized using Fourier transform infrared and differential electronic absorption spectroscopy. The self-assembly of each surfactant was investigated using surface tensiometry. The self-immolative nature of these compounds was analyzed through study of their behavior in response to trigger such as medium pH. ADMET-SAR (adsorption, distribution, metabolism, excretion, toxicity – structure-activity relationship) profiles of synthesized surfactants were generated using admetSAR v. 1.0). The cetrimonium drugs exhibited better profiles than the corresponding pure drugs, save the aqueous solubility which was reduced due to hydrophobicity of counterions.