Photochemical transformation of the uricosuric drug benzbromarone in aqueous solutions exposed to UV irradiation.

As one of benzophenone-derived drugs, benzbromarone (BBM) has been widely used to reduce blood uric acid, treat gout, and gouty arthritis. Understanding the transformation and fate of BBM in natural and engineered systems is critical for its ecological risk assessment. In this study, we systematically investigated the photochemical behavior of BBM in aqueous solutions under laboratory UV254 irradiation. UV-vis spectra show that an aqueous solution of BBM is capable of absorbing UV photons at 200-400 nm. Spectroscopic titration indicates that BBM with a pKa value of 4.83 ± 0.17 is present mainly as the phenolate form under circumneutral conditions. BBM undergoes rapid direct photolysis when exposed to UV254 irradiation and the quantum yields were determined to be 0.0105 and 0.0196 mol E-1 for phenol and phenolate forms, respectively. The heavy atom effect of bromine and spin-orbit coupling effect of aromatic ketone make dibromophenol and carbonyl moieties the critical chromophores accounting for the high photoreactivity of BBM. Laser flash photolysis and electron paramagnetic resonance studies suggest that the photolysis of BBM is initiated by ultrafast photodebromination and Norrish I cleavage. The high yield of bromide determined by ion chromatograph highlights the importance of photodebromination. Due to the light screening effect of wastewater components, the photolysis of BBM in hospital wastewater is inhibited. Photo-induced modification of the dibromophenol moiety of BBM likely generates photoproducts showing toxicity to luminescent bacteria. Overall, our results reveal that photochemical reaction under UV irradiation plays an important role in the attenuation of BBM in engineered water.