Abstract
The phototransformation of naproxen Na in aqueous medium has been investigated. Irradiation of the drug in drinking water affords seven photoproducts. Three of them are dimeric photoproducts isolated for the first time. The compounds, isolated by chromatographic processes, have been identified by spectroscopic means. The toxicity of the photoproducts and the parent drug has been assayed on Daphnia magna and Vibrio fischeri. The results indicate that some photoproducts are more toxic than naproxen.
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References
Alcantara R, Canoira L, Joao P, Rodriguez JG, Vazquez I (2000) Photooxidation of ethylbenzene with air catalyzed by a polymer supported Rose Bengal photosensitizer. J Photochem Photobiol A Chem 133:2–32
Boost G (1975) Clinical-pharmacological and pharmacokinetic studies with naproxen. Arzneimittelforschung 25:281–287
Boscá F, Miranda MA, Vaňó L, Vargas F (1990) New photodegradation pathways for naproxen, a phototoxic non-steroidal anti-inflammatory drug. J Photochem Photobiol A Chem 54:131–134
Daughton CG, Ternes TA (1999) Pharmaceuticals and personal care products in the environment: agents of subtle change? Environ Health Perspect 107 (suppl 6):907–938
DellaGreca M, Fiorentino A, Iesce MR, Isidori M, Nardelli A, Previtera L, Temussi F (2003) Identification of phototransformation products of prednisone by sunlight: toxicity of the drug and its derivatives on aquatic organisms. Environ Toxicol Chem 22:534–539
Diffey BL, Daymond TJ, Fairgreaves H (1983) Phototoxic reactions to piroxicam, naproxen and tiaprofenic acid. Br J Reumatol 22:239–242
IMS Health Canada Ltd (2002) Compendium of pharmaceuticals and specialties, The Canadian drug reference for health professionals
International Organization for Standardization (1996) Water quality: determination of the inhibition of the mobility of Daphnia magna Straus (cladocera, Crustacea)-Acute toxicity test ISO/6341, Geneva, Switzerland
International Organization for Standardization (1998) Water Quality: determination of the inhibitory effect of water samples on the light emission of Vibrio fischeri (Luminescent bacteria test) – Part 3: method using freeze-dried bacteria. ISO/11348-3. Geneva, Switzerland
Ljunggren B, Lundberg K (1985) In vivo phototoxicity of non-steroidal anti-inflammatory drugs evaluated by the mouse-tail technique. Photodermatol 2:377–382
Osamu F, Satoshi S, Yasutaka I (2001) Preparation of hydroperoxides by N-hydroxyphtalimide-catalyzed aerobic oxidation of alkylbenzenes and hydroaromatic compounds and its application. Adv Synth Catal 343:809–813
Ternes TA (1998) Occurrence of drugs in German sewage treatment plants and rivers. Water Resour 32:3245-3260
Acknowledgements
This work was supported by the Ministero Istruzione Università e Ricerca in the frame of PRIN 2002 (Progetto Ricerca Interesse Nazionale). NMR experiments were performed at the Centro Interdipartimentale di metodologie chimico-fisiche on a Varian 500 Inova spectrometer of the Consortium Interuniversitario Nazionale Consorzio Ambiente (Cluster 11-A, Project P0, L.488).
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DellaGreca, M., Brigante, M., Isidori, M. et al. Phototransformation and ecotoxicity of the drug Naproxen-Na. Environ Chem Lett 1, 237–241 (2003). https://doi.org/10.1007/s10311-003-0045-4
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DOI: https://doi.org/10.1007/s10311-003-0045-4