Ketoprofen‐induced photoallergic dermatitis

Nihira, Takashi; Hagiwara, Yusuke

doi:10.1111/ped.13850

Cited by 4 publications

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References 5 publications

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“…The nonsteroidal anti-inflammatory drug ketoprofen (KP, 2-(3-Benzoylphenyl) propanoic acid) causes photo-contact dermatitis under ultraviolet light as a side effect [ 3 , 4 , 5 , 6 , 7 , 8 ]. Also, it is known that its photoproducts may induce photoallergic reactions [ 9 , 10 ]. Due to the presence of a benzophenone chromophore in KP structures ( Figure 1 ), it can participate in various photo–redox processes with the formation of toxic free radicals and potentially allergic photoproducts.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Oxidation of Lipid Membranes in the Presence of the Nonsteroidal Anti-Inflammatory Drug Ketoprofen

et al. 2022

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The damage of cell membranes induced by photosensitive drugs has attracted the significant attention of researchers in various fields of medicine. Ketoprofen (KP) is known to be the most photosensitive among the nonsteroidal anti-inflammatory drugs. The phototoxic side effects of KP and other non-steroidal anti-inflammatory drugs are associated with the action of free radicals, but there is insufficient information about the nature of these radicals. In the present study, free radicals formed upon KP irradiation within lipid membranes were studied using nuclear magnetic resonance (NMR) and chemically induced dynamic nuclear polarization (CIDNP) methods, as well as a molecular dynamics simulation. Our study confirmed the effective penetration of KP into the lipid bilayer and showed a significant effect of the nature of the medium on the photolysis mechanism. While, in a homogeneous solution, the main channel of KP photolysis is free radical-mediated monomolecular decomposition with formation of radical pairs of benzyl and CO2H● radicals, then, in the lipid membrane, the reaction route shifts towards the bimolecular reaction of KP photoreduction. In addition, the effect of the presence an electron donor (the amino acid tryptophan) on lipid oxidation has been studied. It was found that photoreaction of KP with tryptophan proceeds more efficiently than with lipid molecules.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Oxidation of Lipid Membranes in the Presence of the Nonsteroidal Anti-Inflammatory Drug Ketoprofen

et al. 2022

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“…The nonsteroidal anti-inflammatory drug (NSAID) ketoprofen (KP) is known to be highly photosensitive and may induce phototoxic and photoallergic reactions. [1][2][3][4][5][6][7][8][9][10][11][12] Due to its benzophenone-like structure, KP can participate in various photo-redox processes resulting in the formation of toxic free radicals and potentially allergenic photoproducts. In aqueous solutions in the absence of hydrogen donors, the photodegradation of KP occurs via two parallel pathways: photoionization and intramolecular electron transfer.…”

Section: Introductionmentioning

confidence: 99%