Photodegradation of Nabumetone in aqueous solutions

[EN]The photolability of the anti-inflammatory drug Nabumetone (4-(6-methoxy-2-naphthyl)-butan-2-one) was studied in water. The photoproducts were followed by UV-Vis absorption, fluorescence and FTIR spectroscopies as well as gas chromatography–mass spectrometry (GC–MS). The photodegradation process...

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Detalhes bibliográficos
Autores: Valero Juan, Margarita, Costa, Silvia M.B
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2003
País:España
Recursos:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:dnet:gredos______::46080e311e2df2194fbbf0b1d336073f
Acesso em linha:http://hdl.handle.net/10366/171029
Access Level:acceso abierto
Palavra-chave:Nabumetone
Photodegradation
UV-Vis absorption spectroscopy
Fluorescence
FTIR spectroscopy
Gas chromatography–mass spectrometry
Gas Chromatography-Mass Spectrometry
cromatografía de gases y espectrometría de masas
fluorescencia
Descrição
Resumo:[EN]The photolability of the anti-inflammatory drug Nabumetone (4-(6-methoxy-2-naphthyl)-butan-2-one) was studied in water. The photoproducts were followed by UV-Vis absorption, fluorescence and FTIR spectroscopies as well as gas chromatography–mass spectrometry (GC–MS). The photodegradation process in water followed first-order kinetics, with an half-life, t1/2 = 9.7min whereas leading to different products. In this medium, the side chain is photoxidised to 6-methoxy-2-naphthalene aldehyde, as major product, probably via a Nabumetone radical cation formation and the addition of singlet oxygen generated in the drug photolysis. In addition the (4-(6-methoxy-2-naphthyl)-3-buten-2-one) was detected. The most likely origin of the unsaturated compound is the dehydratation of an alcoholic derivative in alpha position of the naphthalene ring, produced via the same radical cation.