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, inhaled, topical
ATC code	D07AC17 (WHO) R01AD08 (WHO) R03BA05 (WHO);
Legal status
Legal status	CA: ℞-only ;
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	444.508 g/mol 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 are two manufactured steroids used to treat nasal symptoms.^[1]^[2]^[3]^[4]^[5] Both the esters, fluticasone furoate and fluticasone propionate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison.^[3]^[2]^[4]^[6]

References[edit]

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, inhaled, topical
ATC code	D07AC17 (WHO) R01AD08 (WHO) R03BA05 (WHO)
Legal status
Legal status	CA: ℞-only
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	444.508 g/mol 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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