Abstract |
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In the present study we investigated the photochemical behaviour of the anti-inflammatory drug fluticasone propionate (1) under aerobic as well as in anaerobic condition with different irradiation wavelengths (254 nm and 310 nm) in acetonitrile and propanol. Photoproducts obtained were isolated and characterized on the basis of IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. The products were: 6,9 Difluro-11-Hydroxy-16 Methyl-3-oxo-17-(1oxopropoxy) 5cycloandrosata-3ene-2,-17-Carbothioic acid- S-(fluro methyl)ester 2 (254 nm), 6,9 Difluro-11-hydroxy-16-Methyl -3oxo-17-(1oxopropoxy)-18,20-Cycloandrosta -1-4 diene-17-carbothioic acid-S-(fluromethyl) ester 3 (310 nm/ propanol, anaerobic), 6, 9 Difluro-17-hydroperoxy-16-methyl-3-oxo-17-(1oxopropoxy) pregn-1,4-diene-3-one 4 (310 nm/aerobic/ Propanol). Due to U.V light interaction Cyclohexadienone moiety in ring A and keto group at C-17 were found to be deeply modified and therefore loss of biological activity during storage and in vivo cannot be ruled out. |