4211. Fluticasone Propionate

Nomenclature

CAS number: 80474-14-2
(6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester; S-fluoromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate; CCI-18781; Cutivate (GSK); Flixonase (GSK); Flixotide (GSK); Flonase (GSK); Flovent (GSK); Flunase (GSK).
C25H31F3O5S; mol wt 500.57.
C 59.99%, H 6.24%, F 11.39%, O 15.98%, S 6.41%.

Description and references

Derivative of flumethasone, q.v. Prepn: NL 81 00707; G. H. Phillipps et al., US 4335121 (1981, 1982 both to Glaxo). Series of articles on structure-activity, pharmacology and clinical studies: Respir. Med. 84, Suppl. A, 19-35 (1990). Clinical trials in allergic rhinitis: E. O. Meltzer et al., J. Allergy Clin. Immunol. 86, 221 (1990). Evaluation in untreated celiac disease: H. C. Mitchison et al., Gut 32, 260 (1991). Clinical trials in COPD: P. L. Paggiaro et al., Lancet 351, 773 (1998); P. S. Burge et al., Br. Med. J. 320, 1297 (2000). Clinical comparison with zafirlukast, in persistant asthma: J. H. Brabson et al., Am. J. Med. 113, 15 (2002). Clinical trial in asthma in adults: M. Masoli et al., Eur. Respir. J. 28, 960 (2006); in children: R. L. Wasserman et al., Ann. Allergy Asthma Immunol. 96, 808 (2006).

Chemical structure

Properties

Crystals, mp 272-273° (dec). [α]D +30° (c = 0.35). Practically insol in water. Freely sol in DMSO, DMF; slightly sol in methanol, 95% ethanol.

Therapeutic Category

Antiallergic; antiasthmatic; anti-inflammatory.

Therapeutic Category (Veterinary)

Antihistaminic; anti-inflammatory.

Keywords

Antiallergic (Steroidal, Nasal); Glucocorticoid; Antiasthmatic (Steroidal, Inhalant)