Benoxaprofen (2-(4-chlorophenyl)-${alpha}$ -methyl-5-benzoxazole acetic acid) is a nonsteroidal anti-inflammatory drug that causes acute cutaneous phototoxicity. The ability of benoxaprofen (BXP) and its photoproduct, decarboxybenoxaprofen (DBXP) to photosensitize the decomposition of tryptophan was evaluated in various media such as water, ethanol and aqueous micellar dispersions of surfactants. The weak photosensitization of BXP in water was found to be enhanced in cationic CTAB micelle system, but yielded little difference in anionic SDS micelles. In ethanol solution, BXP was determined to photosensitize the decomposition of tryptophan, but no photosensitization was observed with DBXP. All of these results implicate that the anion radical of BXP may play a major role in the photosensitization in hydrophobic micellar phase, forming superoxide through interaction with oxygen as demonstrated by observation that the photosensitization was inhibited by superoxide dismutase.