Fluticasone furoate

Fluticasone furoate
Systematic (IUPAC) name

(6α,11β,16α,17α)-6,9-difluoro-17-{[(fluoro-methyl)thio]carbonyl}-11-hydroxy-16-methyl-3-oxoandrosta-1,4-dien-17-yl 2-furancarboxylate
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	C for Intranasal
Routes of administration	Intranasal
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	0.51% (Intranasal)
Protein binding	91%
Metabolism	Intranasal Hepatic (CYP3A4-mediated)
Biological half-life	10 hours
Excretion	Renal
Identifiers
CAS Number	80474-14-2
ATC code	R01AD12 (WHO) R03BA09
PubChem	CID 9854489
DrugBank	DB00588
ChemSpider	8030195
UNII	JS86977WNV^Y
ChEBI	CHEBI:74899
ChEMBL	CHEMBL1676
Chemical data
Formula	C₂₇H₂₉F₃O₆S
Molar mass	538.576 g/mol
SMILES C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)SCF)OC(=O)C5=CC=CO5)C)O)F)C)F
InChI InChI=1S/C27H29F3O6S/c1-14-9-16-17-11-19(29)18-10-15(31)6-7-24(18,2)26(17,30)21(32)12-25(16,3)27(14,23(34)37-13-28)36-22(33)20-5-4-8-35-20/h4-8,10,14,16-17,19,21,32H,9,11-13H2,1-3H3/t14-,16+,17+,19+,21+,24+,25+,26+,27+/m1/s1 Key:XTULMSXFIHGYFS-VLSRWLAYSA-N

Fluticasone furoate is a synthetic corticosteroid derived from fluticasone, marketed by GlaxoSmithKline as Veramyst (US) and Avamys (Australia, Canada, EU, South Africa, South America, Mexico, Israel, and South Korea) for the treatment of allergic rhinitis. It is marketed under the name Furamist in India by Cipla. In India it is also marketed by Dr Reddys under the trade name Ennhale. It can be administered by a nasal spray.^[1]

The combination drug fluticasone furoate/vilanterol is approved for use in the United States by the Food and Drug Administration for long-term maintenance treatment of airflow obstruction in patients with COPD, including chronic bronchitis and emphysema.^[2]

References

↑ Bruni FM, De Luca G, Venturoli V, Boner AL (2009). "Intranasal corticosteroids and adrenal suppression". Neuroimmunomodulation 16 (5): 353–62. doi:10.1159/000216193. PMID 19571596.
↑ "FDA approves Breo Ellipta to treat chronic obstructive pulmonary disease". Food and Drug Administration. May 10, 2013.

Glucocorticoids and antiglucocorticoids (H02)

Glucocorticoids

Pregnene	Cortisone

Pregnenedione	Hydrocortisone (cortisol)^# (Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone butyrate) Budesonide Ciclesonide Deflazacort Medrysone Tixocortol Halogenated at 6: Cloprednol Halogenated, with FG at 16: Halcinonide

Pregnadiene	Rimexolone Halogenated, with FG at 16: Flunisolide Triamcinolone Amcinonide Fluocinolone acetonide (Fluocinonide)

Pregnadienediol	Prednisone (Meprednisone) Halogenated at 9: Fluorometholone Halogenated, with FG at 16: Fluocortolone (Clocortolone Diflucortolone Fluocortin) Desoximetasone

Pregnadienetriol	Prednisolone^# (Methylprednisolone Methylprednisolone aceponate Prednicarbate Prednylidene) Desonide Halogenated: Fluprednisolone (Difluprednate Fluperolone) Halogenated, with FG at 16: Dexamethasone^# Betamethasone (Clobetasol Clobetasone Diflorasone Halometasone Ulobetasol) Beclometasone Paramethasone Alclometasone Fluclorolone acetonide Flumetasone Fluprednidene

Pregnatriene	Cortivazol

Androstene	Halogenated, with FG at 16: Fluticasone (Fluticasone propionate Fluticasone furoate)

Others/unsorted	Halogenated: Loteprednol Halogenated, with FG at 16: Fludroxycortide Formocortal Mometasone furoate Promestriene

Antiglucocorticoids

SGRMs: Dagrocorat^§
Fosdagrocorat^§
Mapracorat^†

Antagonists: Ketoconazole
Mifepristone

Synthesis modifiers

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Decongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain	Cyclopentamine Ephedrine Epinephrine Fenoxazoline Levomethamphetamine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline

Antiallergic agents, excluding corticosteroids	Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide)

Corticosteroids	Beclometasone dipropionate Betamethasone Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone Mometasone furoate Prednisolone Tixocortol Triamcinolone

Other nasal preparations	Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water

Systemic use:
Sympathomimetics

Glucocorticoid signaling

Receptor
(ligands)

Agonists	5α-Dihydrocorticosterone 11-Deoxycorticosterone (desoxycortone, cortexone) 11-Deoxycortisol (cortodoxone, cortexolone)) 15β-Hydroxycyproterone acetate 17-Hydroxyprogesterone 21-Deoxycortisol Acrocinonide Alclometasone Amcinafal Amcinafide Amcinonide Amebucort Amelometasone Amicinonide Anecortave AZD5423 Beclometasone Beclometasone dipropionate Betamethasone Betamethasone acibutate Betamethasone dipropionate Budesonide Butixocort Chlormadinone acetate Chloroprednisone Ciclesonide Cicortonide Ciprocinonide Clobetasol Clobetasol propionate Clobetasone Clocortolone Cloprednol Cloticasone Cormetasone Corticosterone Cortisone Cortisuzol Cortivazol Cyproterone Cyproterone acetate Deflazacort Deprodone Descinolone Desonide Desoximetasone Dexbudesonide Dexamethasone Dexamethasone acefurate Dexamethasone cipecilate Dexamethasone isonicotinate Dichlorisone Diflorasone Difluocortolone Difluocortolone valerate Difluprednate Domoprednate Doxibetasol Drocinonide Etiprednol dicloacetate Fluazacort Fluclorolone Fluclorolone (flucloronide) Fludrocortisone Fludroxycortide Flumoxonide Flumetasone Flunisolide Fluocinolone Fluocinolone acetonide Fluocinonide Fluocortin Fluocortolone Fluorometholone Fluperolone Fluperolone acetate Fluprednidene Fluprednidene acetate Fluprednisolone Fluticasone Fluticasone furoate Fluticasone propionate Formocortal GSK-9027 Halcinonide Halocortolone Halometasone Halopredone Hydrocortamate Hydrocortisone (cortisol) Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone-17-butyrate Hydrocortisone-21-butyrate Icometasone enbutate Isoflupredone Isoprednidene Itrocinonide Locicortolone dicibate Loteprednol Mazipredone Meclorisone Medroxyprogesterone acetate Megestrol acetate Medrysone Meprednisone Methylprednisolone Methylprednisolone aceponate Methylprednisolone suleptanate Mometasone Mometasone furoate Naflocort Nestorone Nicocortonide Nivacortol Oxisopred Paramethasone Prednazate Prednazoline Prednicarbate Prednimustine Prednisolamate Prednisolone Prednisolone steaglate Prednisone Prednylidene Procinonide Progesterone Promestriene Resocortol Rimexolone Rofleponide Tetrahydrocorticosterone Tetrahydrogestrinone Timobesone Tipredane Tixocortol Tixocortol pivalate Tralonide Triamcinolone Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide Triclonide Ulobetasol (halobetasol)

Mixed (SEGRAs)	Dagrocorat Fosdagrocorat Mapracorat

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Asoprisnil C108297 C113176 CORT-108297 Cyproterone acetate Guggulsterone Ketoconazole Lilopristone LLY-2707 Miconazole Mifepristone Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Spironolactone Telapristone Tibolone Toripristone Ulipristal acetate

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycorticosterone

Indirect	ACTH (corticotropin) CRH DHEA DHEA sulfate Plasma proteins (albumin, transcortin) Vasopressin

See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics

GlaxoSmithKline

Subsidiaries

Predecessors,
acquisitions

Products

Current

Pharmaceuticals	Advair Alli Augmentin Avandia Beconase Boniva Flixonase Hycamtin Lamictal Paxil/Seroxat Serlipet Tagamet Ventolin Wellbutrin/Zyban Zantac … more

Vaccines	Hepatyrix Pandemrix Twinrix

Other	Aquafresh Horlicks Nicoderm Nicorette NiQuitin Sensodyne Tums … more

Former

People

Governance	Chris Gent (chair) Andrew Witty (CEO)

Other	Thomas Beecham Silas M. Burroughs Mahlon Kline John K. Smith Henry Wellcome

Litigation

Other

Category

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