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Synthesis and anti-inflammatory properties of budesonide, a new non-halogenated glucocorticoid with high local activity

Thalén, A.; Brattsand, R.

Arzneimittel-Forschung 29(11): 1687-1690

1979

ISSN/ISBN: 0004-4172
PMID: 543875
Document Number: 148431
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.

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