1468. Budesonide

Nomenclature

CAS number: 51333-22-3
(11β,16α)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione; (R,S)-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with butyraldehyde; S-1320; Bidien (IDI); Budeson (AstraZeneca); Cortivent (AstraZeneca); Desonax (Pulitzer); Entocort (AstraZeneca); Miflonil (Novartis); Novopulmon (Viatris); Pulmaxan (AstraZeneca); Preferid (AstraZeneca); Pulmicort (AstraZeneca); Rhinocort (AstraZeneca); Spirocort (AstraZeneca).
C25H34O6; mol wt 430.53.
C 69.74%, H 7.96%, O 22.30%.

Description and references

Non-halogenated glucocorticoid related to triamcinolone hexacetonide, q.v. with a high ratio of topical to systemic activity. Prepn: R. L. Brattsand et al., DE 2323215; eidem, US 3929768 (1973, 1975 both to Bofors). Synthesis and anti-inflammatory properties: A. Thalén, R. L. Brattsand, Arzneim.-Forsch. 29, 1787 (1979). Pharmacokinetic study: A. Ryrfeldt et al., J. Steroid Biochem. 10, 317 (1979). HPLC determn of epimers, impurities, content: G. Roth et al., J. Pharm. Sci. 69, 766 (1980). Clinical experience in collagenous colitis: S. Miehlke et al., Aliment. Pharmacol. Ther. 22, 1115 (2005). Safety profile in asthma patients: A. L. Sheffer et al., Ann. Allergy Asthma Immunol. 94, 48 (2005). Review of physical and pharmocokinetic properties: E. J. O'Connell, Clin. Ther. 25, C42-C60 (2003); of pharmacokinetics and clinical experience in Crohn's disease: S. Edsbcker, T. Andersson, Clin. Pharmacokinet. 43, 803-821 (2004); in allergic rhinitis: B. E. Stanaland, Clin. Ther. 26, 473-492 (2004); in pediatric asthma: W. E. Berger, Drugs 65, 1973-1989 (2005).

Chemical structure

Properties

Crystals, mp 221-232° (dec). Mixture of two isomers; the content of the S-isomer in the mixture varies between 40-51%. [α]D25 +98.9° (c = 0.28 in methylene chloride). Freely sol in chloroform; sparingly sol in ethanol. Practically insol in water, heptane. Partition coefficient (octanol/water): 1.6×103.

Therapeutic Category

Anti-inflammatory.

Therapeutic Category (Veterinary)

Anti-inflammatory in treatment of inflammatory intestinal diseases.

Keywords

Antiasthmatic (Steroidal, Inhalant); Glucocorticoid