Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate.
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.
Bardsley
Ben
B
Chemical Development, GlaxoSmithKline R&D, Gunnels Wood Road, Stevenage, United KingdomSG1 2NY. ben.2.bardsley@gsk.com
Smith
Marco S
MS
Gibbon
Bob H
BH
D000730:Androstadienes / Q000737:chemistry*; D018926:Anti-Allergic Agents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D015394:Molecular Structure; D010782:Photolysis; D011965:Receptors, Glucocorticoid / Q000819:agonists*; D012220:Rhinitis / Q000188:drug therapy*; D012221:Rhinitis, Allergic, Perennial / Q000188:drug therapy; D006255:Rhinitis, Allergic, Seasonal / Q000188:drug therapy
D000730:Androstadienes; D018926:Anti-Allergic Agents; D011965:Receptors, Glucocorticoid; C523187:fluticasone furoate