U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29F3O6S
Molecular Weight 538.5779
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTICASONE FUROATE

SMILES

C[C@]1([H])C[C@@]2([H])[C@]3([H])C[C@@]([H])(C4=CC(=O)C=C[C@]4(C)[C@]3([C@]([H])(C[C@]2(C)[C@]1(C(=O)SCF)OC(=O)c5ccco5)O)F)F

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
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/pro/veramyst.html | http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205625s000lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/204275s000lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022051s011lbl.pdf

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Veramyst

Approved Use

Veramyst is indicated for the treatment of the symptoms of seasonal and perennial allergic rhinitis in patients aged 2 years and older.

Launch Date

1.17754561E12
Preventing
ARNUITY ELLIPTA

Approved Use

RNUITY™ ELLIPTA® is indicated for the once-daily maintenance treatment of asthma as prophylactic therapy in patients aged 12 years and older.

Launch Date

1.40840639E12
Primary
BREO ELLIPTA

Approved Use

BREO® ELLIPTA® 100/25 is a combination inhaled corticosteroid/long-acting beta2-adrenergic agonist (ICS/LABA) indicated for the long-term, once-daily, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema.

Launch Date

1.36805758E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4224 pg/mL
250 μg single, intravenous
dose: 250 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUTICASONE FUROATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3505 pg × h/mL
250 μg single, intravenous
dose: 250 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUTICASONE FUROATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.7 h
250 μg single, intravenous
dose: 250 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUTICASONE FUROATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
FLUTICASONE FUROATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
250 ug single, intravenous
Highest studied dose
Dose: 250 ug
Route: intravenous
Route: single
Dose: 250 ug
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Other AEs: Headache, Catheter site pain...
Other AEs:
Headache (48 patients)
Catheter site pain (26 patients)
Sources:
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Other AEs: Headache, Excoriation...
Other AEs:
Headache (68 patients)
Excoriation (11 patient)
Lethargy (10 patients)
Diarrhoea (10 patients)
Oropharyngeal pain (42 patients)
Sources:
880 ug single, intranasal
Dose: 880 ug
Route: intranasal
Route: single
Dose: 880 ug
Sources:
healthy, 40.5 ± 12.4 years (range: 22–59 years)
n = 17
Health Status: healthy
Age Group: 40.5 ± 12.4 years (range: 22–59 years)
Sex: M+F
Population Size: 17
Sources:
Other AEs: Headache...
Other AEs:
Headache (mild, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Catheter site pain 26 patients
250 ug single, intravenous
Highest studied dose
Dose: 250 ug
Route: intravenous
Route: single
Dose: 250 ug
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Headache 48 patients
250 ug single, intravenous
Highest studied dose
Dose: 250 ug
Route: intravenous
Route: single
Dose: 250 ug
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Diarrhoea 10 patients
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Lethargy 10 patients
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Excoriation 11 patient
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Oropharyngeal pain 42 patients
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Headache 68 patients
800 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 800 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 800 ug, 1 times / day
Sources:
healthy, 20-59 years
n = 79
Health Status: healthy
Age Group: 20-59 years
Sex: M+F
Population Size: 79
Sources:
Headache mild, 2 patients
880 ug single, intranasal
Dose: 880 ug
Route: intranasal
Route: single
Dose: 880 ug
Sources:
healthy, 40.5 ± 12.4 years (range: 22–59 years)
n = 17
Health Status: healthy
Age Group: 40.5 ± 12.4 years (range: 22–59 years)
Sex: M+F
Population Size: 17
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 0.2 uM]
yes [IC50 0.58 uM]
yes [IC50 0.74 uM]
yes [IC50 2.4 uM]
yes [IC50 2.6 uM]
yes [IC50 3.2 uM]
yes [IC50 4 uM]
yes [IC50 5.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
weak (co-administration study)
Comment: administered with ketoconazole; modest increase in mean FF AUC(0-24) and Cmax (by 36% and 33%, respectively)
Page: 11;34
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Adults and adolescents ≥12 years: 110 ug (2 sprays per nostril) once daily
Route of Administration: Nasal
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
ALLERMIST
Brand Name English
GSK 685 698
Code English
FLUTICASONE FUROATE [JAN]
Common Name English
FLUTICASONE FUROATE [MART.]
Common Name English
GSK685968
Code English
(6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-17-(((FLUORO-METHYL)THIO)CARBONYL)-11-HYDROXY-16-METHYL-3-OXOANDROSTA-1,4-DIEN-17-YL 2-FURANCARBOXYLATE
Systematic Name 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
GSK-685968
Code 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 Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-VATC QR01AD12
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-ATC R01AD12
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-ATC R03AL08
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
EMA ASSESSMENT REPORTS ALISADE (WITHDRAWN)
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
EMA ASSESSMENT REPORTS REVINITY ELLIPTA (AUTHORIZED: ASTHMA)
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-ATC R03AL08
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
NCI_THESAURUS C521
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-ATC R03AK10
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-ATC R03BA09
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
EMA ASSESSMENT REPORTS AVAMYS (AUTHORIZED)
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
WHO-VATC QR03AK10
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
Code System Code Type Description
RXCUI
705022
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY RxNorm
INN
8521
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
NCI_THESAURUS
C77003
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
DRUG CENTRAL
4554
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
WIKIPEDIA
FLUTICASONE FUROATE
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
CAS
397864-44-7
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
PUBCHEM
9854489
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
DRUG BANK
DB08906
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
FDA UNII
JS86977WNV
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
EVMPD
SUB26593
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
MERCK INDEX
M11711
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL1676
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY
MESH
C523187
Created by admin on Fri Jun 25 23:54:45 UTC 2021 , Edited by admin on Fri Jun 25 23:54:45 UTC 2021
PRIMARY