UV-induced photodegradation of oseltamivir (Tamiflu) in water

作者：Tong Alfred Y C^*; Braund Rhiannon; Tan Eng W; Tremblay Louis A; Stringer Tristan; Trought Katherine; Peake Barrie M

来源：Environmental Chemistry, 2011, 8(2): 182-189.

DOI：10.1071/EN10095

• advanced oxidation process
• antivirals
• ecotoxicity
• pharmaceuticals

Aqueous solutions of the antiviral drug oseltamivir phosphate (OSP, Tamiflu, (3R,4R,5S)-ethyl 4-acetamido5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate) were degraded using advanced oxidation processes (AOPs) involving photodegradation with UV alone, UV/H(2)O(2) and UV/H(2)O(2)/Fe(II) (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 degrees C in pH 7 phosphate-buffered Milli-Q water. The rate of UV/H(2)O(2) 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 (center dot)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.

• 出版日期2011