UV-induced photodegradation of oseltamivir (Tamiflu) in water
Alfred Y. C. Tong A B E , Rhiannon Braund B , Eng W. Tan A , Louis A. Tremblay C , Tristan Stringer D , Katherine Trought D and Barrie M. Peake A E
+ Author Affiliations
- Author Affiliations
A Chemistry Department, University of Otago, PO Box 56, Dunedin 9054, New Zealand.
B New Zealand National School of Pharmacy, University of Otago, PO Box 56, Dunedin 9054, New Zealand.
C Cawthron Institute, Private Bag 2, Nelson, New Zealand.
D Landcare Research, PO Box 40, Lincoln 7640, New Zealand.
E Corresponding authors. Email: alfred.tong@otago.ac.nz; bpeake@chemistry.otago.ac.nz
Environmental Chemistry 8(2) 182-189 https://doi.org/10.1071/EN10095
Submitted: 24 August 2010 Accepted: 7 February 2011 Published: 2 May 2011
Environmental context. Oseltamivir (Tamiflu) is widely used to prevent and treat influenza but conventional wastewater processes involving sedimentation and biotic oxidation do not appear to significantly remove it from sewage, leading to its discharge into the environment. A range of advanced oxidation processes (AOPs) involving photolysis of aqueous solutions of oseltamivir with UV alone, UV/H2O2 and UV/H2O2/FeII is demonstrated to lead to photodegradation of oseltamivir to products with no ecotoxicity observed. These AOPs may therefore offer potentially environmentally friendly sewage water treatment options.
Abstract. Aqueous solutions of the antiviral drug oseltamivir phosphate (OSP, Tamiflu, (3R,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate) were degraded using advanced oxidation processes (AOPs) involving photodegradation with UV alone, UV/H2O2 and UV/H2O2/FeII (photo-Fenton reaction). The photodecay of the parent OSP in all three cases followed first-order kinetics with respective rate constants of 0.21, 1.56 and 1.75 min–1 at 20°C in pH 7 phosphate-buffered Milli-Q water. The rate of UV/H2O2 photolysis in the presence of 2-methylpropan-2-ol was significantly slower with an approximate first-order rate constant of 0.13 min–1 suggesting the involvement of •OH in the degradation process. NMR spectroscopy, mass spectrometry and high-performance liquid chromatography (HPLC) with UV diode array detection were used to identify the crude photoproduct as the hydroxylated OSP derivative (3S,4R,5S)-ethyl 4-acetamido-5-amino-2-hydroxy-3-(pentan-3-yloxy)cyclohexanecarboxylate that occurs by an unknown mechanism. OSP and this crude photoproduct demonstrated no effect on the survival of Quinquelaophonte sp. over 96 h.
Additional keywords: advanced oxidation process, antivirals, ecotoxicity, pharmaceuticals.
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