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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29F3O6S
Molecular Weight 538.576
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTICASONE FUROATE

SMILES

C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(OC(=O)C5=CC=CO5)C(=O)SCF

InChI

InChIKey=XTULMSXFIHGYFS-VLSRWLAYSA-N
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

HIDE SMILES / InChI

Description

Fluticasone furoate is a synthetic trifluorinated corticosteroid with potent anti-inflammatory activity. Fluticasone furoate is a anti-allergic agents that is FDA approved for the treatment of symptoms of seasonal and perennial allergic rhinitis, asthma and for reducing exacerbations in patients with chronic obstructive pulmonary disease. Fluticasone furoate has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor. The clinical relevance of these findings is unknown. The most common adverse reactions (>1% incidence) included headache, epistaxis, pharyngolaryngeal pain, nasal ulceration, back pain, pyrexia, and cough. Coadministration of ritonavir is not recommended. Use caution with coadministration of other potent CYP3A4 inhibitors, such as ketoconazole.

CNS Activity

Originator

Approval Year

Target InfoCondition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
BREO ELLIPTA
Preventing
ARNUITY ELLIPTA
Palliative
Veramyst
PMID

PMID

TitleDatePMID
Inhaled corticosteroid and long-acting β2-agonist pharmacological profiles: effective asthma therapy in practice.
2012 Dec
Fluticasone furoate, a novel inhaled corticosteroid, demonstrates prolonged lung absorption kinetics in man compared with inhaled fluticasone propionate.
2013 Jan
Inhaled fluticasone furoate/vilanterol does not affect hypothalamic-pituitary-adrenal axis function in adolescent and adult asthma: randomised, double-blind, placebo-controlled study.
2013 Oct
Patent

Sample Use Guides

In Vivo Use Guide
Adults and adolescents ≥12 years: 110 ug (2 sprays per nostril) once daily
Route of Administration: Nasal
In Vitro Use Guide
The potency of fluticasone furoate in PBMCs from mild asthma (IC50: 1.9±0.64 nM, n= 4) was 2.1 fold higher than fluticasone propionate (4.0±1.6 nM, n= 4).
Name Type Language
FLUTICASONE FUROATE
EMA EPAR   INN   JAN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
TRELEGY ELLIPTA COMPONENT FLUTICASONE FUROATE
Brand Name English
FLUTICASONE FUROATE [VANDF]
Common Name English
FLUTICASONE FUROATE [JAN]
Common Name English
FLUTICASONE FUROATE [MART.]
Common Name English
GSK685968
Code English
FLUTICASONE FUROATE COMPONENT OF TRELEGY ELLIPTA
Brand Name English
ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID, 6,9-DIFLUORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-3-OXO-, S-(FLUOROMETHYL) ESTER, (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-
Common Name English
FLUTICASONE FUROATE [WHO-DD]
Common Name English
GW685698X
Code English
FURAMIST
Brand Name English
FLUTICASONE FUROATE COMPONENT OF ARNUITY ELLIPTA
Brand Name English
FLUTICASONE FUROATE [EMA EPAR]
Common Name English
(6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUOROMETHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL-2-FURANCARBOXYLATE
Common Name English
BREO ELLIPTA COMPONENT FLUTICASONE FUROATE
Brand Name English
(6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUOROMETHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL 2-FUROATE
Common Name English
FLUTICASONE FUROATE [INN]
Common Name English
ENNHALE
Brand Name English
FLUTICASONE FUROATE COMPONENT OF BREO ELLIPTA
Brand Name English
FLUTICASONE FUROATE [MI]
Common Name English
FLUTICASONE FUROATE [ORANGE BOOK]
Common Name English
FLUTICASONE FUROATE [USAN]
Common Name English
ARNUITY ELLIPTA COMPONENT FLUTICASONE FUROATE
Brand Name English
AVAMYS
Brand Name English
VERAMYST
Brand Name English
6.ALPHA.,9-DIFLUORO-17-(((FLUOROMETHYL)SULFANYL)CARBONYL)-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXOANDROSTA-1,4-DIEN-17.ALPHA.-YL FURAN-2-CARBOXYLATE
Common Name English
GW-685698X
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS RELVAR ELLIPTA (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
WHO-VATC QR01AD12
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
WHO-ATC R01AD12
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
EMA ASSESSMENT REPORTS ALISADE (WITHDRAWN)
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
EMA ASSESSMENT REPORTS REVINITY ELLIPTA (AUTHORIZED: ASTHMA)
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
WHO-ATC R03AK10
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
EMA ASSESSMENT REPORTS AVAMYS (AUTHORIZED)
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
WHO-VATC QR03AK10
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
WHO-ATC R03BA09
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
Code System Code Type Description
RXCUI
705022
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY RxNorm
INN
8521
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
NCI_THESAURUS
C77003
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
WIKIPEDIA
FLUTICASONE FUROATE
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
CAS
397864-44-7
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
PUBCHEM
9854489
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB08906
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
EVMPD
SUB26593
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
MERCK INDEX
M11711
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
ChEMBL
CHEMBL1676
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY
MESH
C523187
Created by admin on Tue Mar 06 10:46:44 UTC 2018 , Edited by admin on Tue Mar 06 10:46:44 UTC 2018
PRIMARY