Fluticasone

Fluticasone
Systematic (IUPAC) name
	S-(fluoromethyl) (6S,8S,9R,10S,11S,13S,14S,16R,17R)-; 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-; 6,7,8,11,12,14,15,16-octahydrocyclopenta[a]; phenanthrene-17-carbothioate
Clinical data
AHFS/Drugs.com	monograph
Pregnancy; category	C for Intranasal and Inhaled;
Legal status	UK: POM; US: ℞-only;
Routes	Intranasal, Inhaled, Topical Cream or Ointment
Pharmacokinetic data
Bioavailability	0.51% (Intranasal)
Protein binding	91%
Metabolism	Intranasal; Hepatic (CYP3A4-mediated)
Half-life	10 hours
Excretion	Renal
Identifiers
CAS number	90566-53-3 ; 80474-14-2 (propionate)
ATC code	D07AC17 R01AD08 R03BA05
PubChem	CID 5311101
DrugBank	DB00588
ChemSpider	4470631
UNII	CUT2W21N7U
KEGG	D07981
ChEBI	CHEBI:5134
ChEMBL	CHEMBL1201396
Chemical data
Formula	C22H27F3O4S
Molecular mass	444.508 g/mol
	SMILES O=C(SCF)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C;
	InChI InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 ; Key:MGNNYOODZCAHBA-GQKYHHCASA-N ;
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Fluticasone is a synthetic glucocorticoid.^[1]

Both the furoate and propionate forms are used as topical anti-inflammatories:^[2]

Synthesis[edit]

Fluticasone synthesis:^[3]

^ Briggs, Gerald G.; Freeman, Roger K.; Yaffe, Sumner J. (2012), Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk, Lippincott Williams & Wilkins, p. 600, ISBN 1451153597.
^ Spratto, George R.; Woods, Adrienne L. (2012), Delmar Nurse's Drug Handbook 2012, Cengage Learning, p. 748, ISBN 1111310653.
^ Phillipps, G. H.; Bailey, E. J.; Bain, B. M.; Borella, R. A.; Buckton, J. B.; Clark, J. C.; Doherty, A. E.; English, A. F.; Fazakerley, H. (1994). "Synthesis and Structure-Activity Relationships in a Series of Antiinflammatory Corticosteroid Analogs, Halomethyl Androstane-17.beta.-carbothioates and -17.beta.-carboselenoates". Journal of Medicinal Chemistry 37 (22): 3717. doi:10.1021/jm00048a008. edit