[EN] The photodegradation of Ibuprofen, a widely used non¿steroidal anti¿inflammatory drug (NSAID), was examined. Several photoproducts (I¿VI) were isolated and identified on the basis of their IR¿1H¿NMR¿ and 13C¿NMR¿ spectra. The chemical structures were confirmed by unambiguous alternative synthesis from available reagents. The most significant primary photochemical process was the cleavage of the C¿C bond a to the carboxy group. Subsequent secondary processes (hydrogen abstraction, dimerization, incorporation of methanol, or reaction with oxygen) might account for the formation of the different photoproducts. The cytotoxic effects were assayed using the red¿blood cell lysis test and the enzyme leakage (LDH and GOT) from cultured fibroblasts. Compound V [l¿(4 isobutylphenyl)¿ethanol] was found to be toxic for both system at concentrations greater than 1 mM while compound IV [l¿(4 isobutylphenyl acetophenone)] was toxic for fibroblasts but not for erythrocytes at the same concentration. Ibuprofen and the other photocompounds were apparently non¿toxic. The significance of these results is discussed in connection with the possible in vivo phototoxicity of Ibuprofen.
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