Synthesis and anti-inflammatory properties of budesonide, a new non-halogenated glucocorticoid with high local activity.
As part of a study of the local anti-inflammatory activity of corticosteroid 16 alpha, 17 alpha-acetals it was found that on acetalization of 16 alpha-hydroxyprednisolone with n-butyraldehyde the two possible epimers were formed in the ratio of 1: 1. The reaction product was resolved by column chromatography on Sephadex LH-20. The isolated epimers were studied by NMR and mass spectrometry. The epimeric mixture of this new non-halogenated corticoid, 16 alpha, 17 alpha-(22R,S)-propylmethylenedioxypregna-1,4-diene-11 beta,21-diol-3,20-dione (budesonide), was shown to have a local antiinflammatory potency comparable to that of fluocinolone acetonide in cotton pellet tests in rats. In contrast, its systemic glucocorticoid activity was found to be 4--7 times lower than that of fluocinolone acetonide, however.
D000818:Animals; D019819:Budesonide; D055598:Chemical Phenomena; D002621:Chemistry; D005938:Glucocorticoids / Q000138:chemical synthesis*; D006099:Granuloma / Q000503:physiopathology; D008297:Male; D009929:Organ Size / Q000187:drug effects; D011282:Pregnenediones / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013950:Thymus Gland / Q000187:drug effects; D014222:Triamcinolone Acetonide / Q000494:pharmacology
D005938:Glucocorticoids; D011282:Pregnenediones; D019819:Budesonide; D014222:Triamcinolone Acetonide