Fluticasone Furoate

For research use only. Not for therapeutic Use.

  • CAT Number: I011401
  • CAS Number: 397864-44-7
  • Molecular Formula: C27H29F3O6S
  • Molecular Weight: 538.578
  • Purity: 98%
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Fluticasone furoate (CAT: I011401) is a synthetic corticosteroid with potent anti-inflammatory and immunosuppressive properties. It acts by binding to glucocorticoid receptors and modulating gene expression, resulting in the inhibition of inflammatory mediators and suppression of immune responses. Fluticasone furoate is primarily used as an inhaled corticosteroid for the treatment of asthma and allergic rhinitis. It helps to reduce airway inflammation, improve lung function, and alleviate symptoms such as wheezing, shortness of breath, and nasal congestion. Fluticasone furoate has a long duration of action, allowing for once-daily dosing and providing sustained protection against symptoms. It is considered an effective and well-tolerated medication for managing respiratory conditions.


Catalog Number I011401
CAS Number 397864-44-7
Synonyms

(6α,11β,16α,17α)-6,9-Difluoro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioic Acid S-(Fluoromethyl) Ester; Allermist; Avamys; GSK 685 698; GW 685698X;

Molecular Formula C27H29F3O6S
Purity 98%
Appearance Solid powder
Storage Store at RT
IUPAC Name [(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
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
InChIKey XTULMSXFIHGYFS-VLSRWLAYSA-N
SMILES CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)SCF)OC(=O)C5=CC=CO5)C)O)F)C)F
Reference

1. N Engl J Med. 2016 Sep 29;375(13):1253-60. doi: 10.1056/NEJMoa1608033. Epub 2016
Sep 4.
<br>
Effectiveness of Fluticasone Furoate-Vilanterol for COPD in Clinical Practice.
<br>
Vestbo J(1), Leather D(1), Diar Bakerly N(1), New J(1), Gibson JM(1),
McCorkindale S(1), Collier S(1), Crawford J(1), Frith L(1), Harvey C(1),
Svedsater H(1), Woodcock A(1); Salford Lung Study Investigators.
<br>
Collaborators: Amin J, Austin M, Sharma M, Borg-Constanzi J, Browne N, Buch K,
Budden P, Chaudry A, Cheema L, Chennupati N, Coulson S, Cribbin L, Dillon D,
Farooq B, Finnegan N, Fletcher A, Addlestone L, Hope B, Khan M, White J,
Behardien J, Mafunga C, Malcolmson C, McCarthy D, Milligan H, Raj V, Salim R,
Singh H, Sultan M, Seaton R, Tankel J, Khan R, Tyrell N, Umeadi U, Wright S,
Gibbons C, Brunt C, Gill L, Archer R, Howard R, Breen G, Stratford-Smith P,
Wilson R, Wilkinson H, El-Kafrawy A, Patel P, Iles S, Frier S, Bakhat A, Smith
N, Herron D, Adams-Strump D, Acherakar N, Shah D, Kanumilli N, Afshar A, Stamp
M, Westwood C, Wright A, Richardson K, Jackson P, Jarvis M, Fink P, Lord N,
Hughes C, Ahuja A, Joshi V, Larah D, Levenson S, Malcomson C, Parveen R, Rahman
A, Kassamr N, Kwok S.
<br>
Author information:<br>
(1)From the Centre for Respiratory Medicine and Allergy, Manchester Academic
Health Sciences Centre, University of Manchester and University Hospital of
South Manchester NHS Foundation Trust (J.V., A.W.), Manchester Academic Health
Sciences Centre, University of Manchester and Salford Royal NHS Foundation Trust
(J.M.G.), and NIHR Clinical Research Network Greater Manchester (S.M.),
Manchester; Global Respiratory Franchise (D.L.) and Respiratory Research and
Development (S.C., J.C., L.F., H.S.), GlaxoSmithKline UK, Brentford; Salford
Royal NHS Foundation Trust (N.D.B., J.N., J.M.G.), NorthWest EHealth (J.N.,
J.M.G.), and NHS Salford Clinical Commissioning Group (S.M.), Salford; and
Global Clinical Safety and Pharmacovigilance, Safety Evaluation and Risk
Management, GlaxoSmithKline UK, Uxbridge (C.H.) – all in the United Kingdom.
<br>
Comment in<br>
N Engl J Med. 2016 Dec 29;375(26):2605-2607.
N Engl J Med. 2016 Dec 29;375(26):2606.
N Engl J Med. ;375(26):2605-6.
N Engl J Med. ;375(26):2606-7.
<br>
BACKGROUND: Evidence for the management of chronic obstructive pulmonary disease
(COPD) comes from closely monitored efficacy trials involving groups of patients
who were selected on the basis of restricted entry criteria. There is a need for
randomized trials to be conducted in conditions that are closer to usual
clinical practice.<br>
METHODS: In a controlled effectiveness trial conducted in 75 general practices,
we randomly assigned 2799 patients with COPD to a once-daily inhaled combination
of fluticasone furoate at a dose of 100 μg and vilanterol at a dose of 25 μg
(the fluticasone furoate-vilanterol group) or to usual care (the usual-care
group). The primary outcome was the rate of moderate or severe exacerbations
among patients who had had an exacerbation within 1 year before the trial.
Secondary outcomes were the rates of primary care contact (contact with a
general practitioner, nurse, or other health care professional) and secondary
care contact (inpatient admission, outpatient visit with a specialist, or visit
to the emergency department), modification of the initial trial treatment for
COPD, and the rate of exacerbations among patients who had had an exacerbation
within 3 years before the trial, as assessed in a time-to-event analysis.
RESULTS: The rate of moderate or severe exacerbations was significantly lower,
by 8.4% (95% confidence interval, 1.1 to 15.2), with fluticasone
furoate-vilanterol therapy than with usual care (P=0.02). There was no
significant difference in the annual rate of COPD-related contacts to primary or
secondary care. There were no significant between-group differences in the rates
of the first moderate or severe exacerbation and the first severe exacerbation
in the time-to-event analyses. There were no excess serious adverse events of
pneumonia in the fluticasone furoate-vilanterol group. The numbers of other
serious adverse events were similar in the two groups.
CONCLUSIONS: In patients with COPD and a history of exacerbations, a once-daily
treatment regimen of combined fluticasone furoate and vilanterol was associated
with a lower rate of exacerbations than usual care, without a greater risk of
serious adverse events. (Funded by GlaxoSmithKline; Salford Lung Study
ClinicalTrials.gov number, NCT01551758 .).
<br><br>

2. Lancet. 2016 Apr 30;387(10030):1817-26. doi: 10.1016/S0140-6736(16)30069-1. Epub
2016 Apr 28.
<br>
Fluticasone furoate and vilanterol and survival in chronic obstructive pulmonary
disease with heightened cardiovascular risk (SUMMIT): a double-blind randomised
controlled trial.
<br>
Vestbo J(1), Anderson JA(2), Brook RD(3), Calverley PM(4), Celli BR(5), Crim
C(6), Martinez F(7), Yates J(6), Newby DE(8); SUMMIT Investigators.
<br>
Author information:<br>
(1)Centre for Respiratory Medicine and Allergy, Manchester Academic Health
Sciences Centre, The University of Manchester and South Manchester University
Hospital NHS Foundation Trust, Manchester, UK. Electronic address:
[email protected].
(2)Research & Development, GlaxoSmithKline, Stockley Park, Middlesex, UK.
(3)University of Michigan Health System, Ann Arbor, MI, USA.
(4)University of Liverpool, Department of Medicine, Clinical Sciences Centre,
University Hospital Aintree, Liverpool, UK.
(5)Pulmonary and Critical Care Division, Brigham and Women’s Hospital, Harvard
Medical School, Boston, MA, USA.
(6)Research & Development, GlaxoSmithKline, Research Triangle Park, NC, USA.
(7)University of Michigan Health System, Ann Arbor, MI, USA; Division of
Pulmonary and Critical Care Medicine, Weill Cornell Medicine, New York, NY, USA.
(8)Centre for Cardiovascular Science, University of Edinburgh, Edinburgh, UK.

Comment in<br>
Lancet. 2016 Apr 30;387(10030):1791-2.
Am J Respir Crit Care Med. 2018 Apr 1;197(7):944-946.
<br>
BACKGROUND: Chronic obstructive pulmonary disease (COPD) often coexists with
cardiovascular disease. Treatments for airflow limitation might improve survival
and both respiratory and cardiovascular outcomes. The aim of this study was to
assess whether inhaled treatment with a combined treatment of the
corticosteroid, fluticasone furoate, and the long-acting β agonist, vilanterol
could improve survival compared with placebo in patients with moderate COPD and
heightened cardiovascular risk.<br>
METHODS: In this double-blind randomised controlled trial (SUMMIT) done in 1368
centres in 43 countries, eligible patients were aged 40-80 years and had a
post-bronchodilator forced expiratory volume in 1 s (FEV1) between 50% and 70%
of the predicted value, a ratio of post-bronchodilator FEV1 to forced vital
capacity (FVC) of 0·70 or less, a smoking history of at least 10 pack-years, and
a score of 2 or greater on the modified Medical Research Council dyspnoea scale.
Patients had to have a history, or be at increased risk, of cardiovascular
disease. Enrolled patients were randomly assigned (1:1:1:1) through a
centralised randomisation service in permuted blocks to receive once daily
inhaled placebo, fluticasone furoate (100 μg), vilanterol (25 μg), or the
combination of fluticasone furoate (100 μg) and vilanterol (25 μg). The primary
outcome was all-cause mortality, and secondary outcomes were on-treatment rate
of decline in forced expiratory volume in 1 s (FEV1) and a composite of
cardiovascular events. Safety analyses were performed on the safety population
(all patients who took at least one dose of study drug) and efficacy analyses
were performed on the intention-to-treat population (safety population minus
sites excluded with Good Clinical Practice violations). This study is registered
with ClinicalTrials.gov, number NCT01313676.<br>
FINDINGS: Between Jan 24, 2011, and March 12, 2014, 23 835 patients were
screened, of whom 16 590 were randomised. 16 485 patients were included in the
intention-to-treat efficacy population; 4111 in the placebo group, 4135 in the
fluticasone furoate group, 4118 in the vilanterol group, and 4121 in the
combination group. Compared with placebo, all-cause mortality was unaffected by
combination therapy (hazard ratio [HR] 0·88 [95% CI 0·74-1·04]; 12% relative
reduction; p=0·137) or the components (fluticasone furoate, HR 0·91 [0·77-1·08];
p=0·284; vilanterol, 0·96 [0·81-1·14]; p=0·655), and therefore secondary
outcomes should be interpreted with caution. Rate of decline in FEV1 was reduced
by combination therapy (38 mL per year [SE 2·4] vs 46 mL per year [2·5] for
placebo, difference 8 mL per year [95% CI 1-15]) with similar findings for
fluticasone furoate (difference 8 mL per year [95% CI 1-14]), but not vilanterol
(difference -2 mL per year [95% CI -8 to 5]). Combination therapy had no effect
on composite cardiovascular events (HR 0·93 [95% CI 0·75-1·14]) with similar
findings for fluticasone furoate (0·90 [0·72-1·11]) and vilanterol (0·99
[0·80-1·22]). All treatments reduced the rate of moderate and severe
exacerbation. No reported excess risks of pneumonia (5% in the placebo group, 6%
in the combination group, 5% in the fluticasone furoate group, and 4% in the
vilanterol group) or adverse cardiac events (17% in the placebo group, 18% in
the combination group, and 17% in the fluticasone furoate group, and 17% in the
vilanterol group) were noted in the treatment groups.<br>
INTERPRETATION: In patients with moderate COPD and heightened cardiovascular
risk, treatment with fluticasone furoate and vilanterol did not affect mortality
or cardiovascular outcomes, reduced exacerbations, and was well tolerated.
Fluticasone furoate, alone or in combination with vilanterol, seemed to reduce
FEV1 decline.
FUNDING: GlaxoSmithKline.
<br><br>

3. Expert Rev Respir Med. 2018 Dec;12(12):997-1005. doi:
10.1080/17476348.2018.1548936. Epub 2018 Nov 28.
<br>
Fluticasone furoate, umeclidinium bromide, and vilanterol as a combination
therapy for chronic obstructive pulmonary disease.
<br>
Parri G(1), Nieri D(2), Roggi MA(1), Vagaggini B(1), Celi A(1), Paggiaro P(1).
<br>
Author information:<br>
(1)a Department of Surgery, Medicine, Molecular Biology and Critical Care ,
University of Pisa , Pisa , Italy.<br>
(2)b Bronchology and bronchial endoscopy unit, Department of medical specialties
, S. Maria Annunziata hospital , Bagno a Ripoli (Florence) , Italy.
<br>
Introduction: Triple therapy with two bronchodilators (LABA plus LAMA) and an
inhaled corticosteroid (ICS) is recommended for patients suffering from severe
chronic obstructive pulmonary disease (COPD). Areas covered: All 12-52 week-long
studies comparing triple therapy with umeclidinium (UM) added to either
fluticasone furoate/vilanterol (FF/VI) or fluticasone propionate/salmeterol
(FP/SAL) vs. other comparators in COPD patients of group B or D (2011 GOLD
classification) were considered. When UM was added to ICS/LABA with separate
devices or within a single device, triple combination was more effective than
comparators (usually, ICS/LABA combinations) regarding improvements to pulmonary
function, symptoms, quality of life and, in the longer studies, rate of
moderate-severe exacerbations. The IMPACT study (a large trial comparing
UM/FF/VI with both FF/VI and UM/VI combinations) showed that triple therapy had
a greater effect compared to dual therapies in reducing the rate of
moderate-severe exacerbations, improving trough FEV1 and improving quality of
life. The safety profile was good, without excess cardiovascular effects or
pneumonia, however, the presence of comorbidities was frequent. Expert
commentary: UM/FF/VI combination represents a good option for severe COPD
patients who remain symptomatic and/or with frequent exacerbations despite dual
therapies. Once daily administration with a simple and effective device may
increase adherence and efficacy of the treatment.
<br>

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