Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate
Ben Bardsley,Marco S. Smith,Bob H. Gibbon
Organic & Biomolecular Chemistry Pub Date : 03/05/2010 00:00:00 , DOI:10.1039/B926964A
Abstract

Fluticasone furoate is a novel glucocorticoid receptor agonist marketed as a treatment for seasonal and perennial allergic rhinitis. Forced degradation of fluticasone furoate under conditions of light led to a number of degradation products, the structures of which were elucidated using mass spectrometry and a range of one and two-dimensional NMR experiments. Three structures were derived, including two which involved a rearrangement of the steroid ring A to give cross-linked degradation products. The results demonstrate the applicability of a previously observed mechanism of photodegradation to fluticasone furoate.

Graphical abstract: Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate