PHOTOLYTIC DEGRADATION OF IBUPROFEN. TOXICITY OF THE ISOLATED PHOTOPRODUCTS ON FIBROBLASTS and ERYTHROCYTES

Abstract

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.

Titanium Dioxide Nanoparticle Photocatalysed Degradation of Ibuprofen and Naproxen in Water: Competing Hydroxyl Radical Attack and Oxidative Decarboxylation by Semiconductor Holes

“…Literature, indicate that the photoproduct 1‐(4‐isobutylphenyl)ethanone is toxic and has lytic activity on erythrocytes. 1‐(4‐isobutylphenyl)ethanol has also been shown to have toxic effects in measurements on the amount of cell protein and intracellular enzymatic activity of LDH and GOT in cultured fibroblasts ,…”

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

“…Because pharmaceuticals are released into surface waters via discharge of wastewater treatment plant effluent, photochemical processes may be an important removal process for these compounds. Much of the previous work on the photochemistry of naproxen and ibuprofen has focused on their phototoxicity (Castell et al, 1987;Moore and Chappuis, 1988;Bosca et al, 1990;Condorelli et al, 1993;Jimenez et al, 1997). The conditions of the studies varied widely (e.g., light source, wavelength cutoff, solvent) and have limited environmental relevance.…”

Photodegradation of Some Quinolones Used as Antimicrobial Therapeutics

“…They could be induced by the substances themselves or by derivatives formed as a consequence of UV irradiation. [7][8][9][10] Ferguson et al11 observed a loss of antibacterial activity of ciprofloxacin after UV exposure, suggesting photodegradation of the compound. The photodegradation itself has not yet been documented, as well as no information has been so far provided on the nature of the photoproducts.…”