Fluticasone

Fluticasone
Clinical data
Other names	6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione; S-(Fluoromethyl)-6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate
Routes of; administration	Intranasal, inhalation, topical
ATC code	D07AC17 (WHO) R01AD08 (WHO) R03BA05 (WHO) R01AD58 (WHO);
Legal status
Legal status	CA: OTC;
Pharmacokinetic data
Bioavailability	0.51% (Intranasal)
Protein binding	91.0%
Metabolism	Intranasal; Liver (CYP3A4-mediated)
Elimination half-life	10 hours
Excretion	Kidney
Identifiers
	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;
CAS Number	90566-53-3 ;
PubChem CID	5311101;
IUPHAR/BPS	6699;
DrugBank	DB00588 ;
ChemSpider	4470631 ;
UNII	CUT2W21N7U;
KEGG	D07981 ;
ChEBI	CHEBI:5134 ;
ChEMBL	ChEMBL1201396 ;
CompTox Dashboard (EPA)	DTXSID0044022 ;
Chemical and physical data
Formula	C22H27F3O4S
Molar mass	444.51 g·mol−1
3D model (JSmol)	Interactive image;
	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 manufactured glucocorticoid used to treat nasal congestion. Both the esters, fluticasone propionate (sold as Flovent) and fluticasone furoate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison.

It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 25th most commonly prescribed medication in the United States, with more than 22 million prescriptions, although it is also sold over-the-counter (OTC).

Clinical data

Other names	6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione; S-(Fluoromethyl)-6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate
Routes of administration	Intranasal, inhalation, topical
ATC code	D07AC17 (WHO) R01AD08 (WHO) R03BA05 (WHO) R01AD58 (WHO)
Legal status
Legal status	CA: OTC
Pharmacokinetic data
Bioavailability	0.51% (Intranasal)
Protein binding	91.0%
Metabolism	Intranasal Liver (CYP3A4-mediated)
Elimination half-life	10 hours
Excretion	Kidney
Identifiers
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
CAS Number	90566-53-3^N
PubChem CID	5311101
IUPHAR/BPS	6699
DrugBank	DB00588^N
ChemSpider	4470631^Y
UNII	CUT2W21N7U
KEGG	D07981^Y
ChEBI	CHEBI:5134^N
ChEMBL	ChEMBL1201396^N
CompTox Dashboard (EPA)	DTXSID0044022
Chemical and physical data
Formula	C₂₂H₂₇F₃O₄S
Molar mass	444.51 g·mol⁻¹
3D model (JSmol)	Interactive image
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^Y Key:MGNNYOODZCAHBA-GQKYHHCASA-N^Y
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