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Abstract
Photodegradation of loteprednol etabonate ( 5), a steroid anti-inflammatory drug, in the solid state, in aqueous suspension, and in aqueous acetonitrile solution has been investigated. Analysis by HPLC showed that the profile of photodegradation products in the solid state was qualitatively similar to that in the aqueous suspension, although the profile in the aqueous acetonitrile solution was considerably different. The major photodegradation products were isolated from the aqueous suspension and the aqueous acetonitrile solution by using preparative reversed-phase HPLC and their structures were elucidated on the basis of spectroscopic data. Photolysis in the solid state and in aqueous suspension yielded three rearrangement products, chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-5α-methyl-2-oxo-19-norandrosta-1(10),3-diene-17β-carboxylate ( 8), chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-1-methyl-3-oxo-6(5→10α)- abeo-19-norandrosta-1,4-diene-17β-carboxylate ( 9), and chloromethyl 1β,11β-epoxy-17α-ethoxycarbonyloxy-2-oxo-10α-androsta-4-ene-17β-carboxylate ( 10). In aqueous acetonitrile solution, 10 was the major product, however, 8 and 9 were not obtained. Pathways for the formation of these compounds from loteprednol etabonate ( 5) are proposed.
Published Version
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