General
Preferred name
FLUTICASONE FUROATE
Synonyms
Allermist ()
Breo Ellipta-fluticasone furoate ()
fluticasone furoate  ()
GW685698X ()
GW685698 ()
Furoate de fluticasone ()
Ennhale ()
GSK 685 698 ()
GW-685698X ()
Furoato de fluticasona ()
Relvar ellipta ()
Veramyst ()
Trelegy ellipta ()
Furamist ()
GSK-685968 ()
Arnuity ellipta ()
GSK685968 ()
Flonase sensimist allergy relief ()
Avamys ()
P&D ID
PD009175
CAS
397864-44-7
Tags
available
probe
drug
Approved by
FDA
EMA
PMDA
First approval
2007
Drug indication
Asthma
Drug Status
approved
withdrawn
Max Phase
4.0
Probe info
Probe type
calculated probe
Probe sources
Probe Miner (suitable probes)
Probe targets
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
INDICATION Fluticasone furoate is indicated as an inhaler for the treatment and management of asthma by prophylaxis[FDA Label][F4364]. The fluticasone furoate nasal spray is indicated for treating season and perennial allergic rhinitis[FDA Label][A177130].
ABSORPTION Intranasal exposure of fluticasone furoate results in patients swallowing a larger portion of the dose[FDA Label][A177118]. However, absorption is poor and metabolism is high, therefore there is negligible systemic exposure with a nasal bioavailability of 0.50% and oral bioavialability of 1.26%[FDA Label][A7490]. Inhaled bioavailability is 13.9%[F4364]. A study of 24 healthy Caucasian males showed an inhaled bioavailability of 6.3-18.4%[A7490].
HALF-LIFE 15.1 hours for intranasal fluticasone furoate[FDA Label] and 24 hours for the inhaled formulation[F4364]. A study of 24 healthy Caucasian males showed a half life of 13.6 hours following intravenous administration and 17.3-23.9 hours followed inhalation[A7490].
PHARMACODYNAMICS Systemically, in vitro experiments show fluticasone furoate activates glucocorticoid receptors, inhibits nuclear factor kappa b, and inhibits lung eosinophilia in rats[FDA Label][F4364,A177130].
MOA Fluticasone furoate works through an unknown mechanism to affect the action of various cell types and mediators of inflammation[FDA Label][F4364]. In vitro experiments show fluticasone furoate activating glucocorticoid receptors, inhibiting nuclear factor kappa b, and inhibiting lung eosinophilia in rats[FDA Label][F4364,A177130].
ROE Fluticasone furoate is eliminated ≥90% in the feces and 1-2% in the urine[FDA Label][F4364].
METABOLISM Fluticasone furoate is cleared from hepatic metabolism by cytochrome P450 3A4[FDA Label][F4364,A177121]. Fluticasone furoate is hydrolysed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metabolite[FDA Label][A177118].
TOXICITY Fluticasone furoate administered nasally may be associated with adrenal suppression or an increase in QTc interval though the association has not been well demonstrated in studies[FDA Label][A7488]. Fluticasone furoate requires no dosage adjustment in renal impairment but must be used in caution in hepatic impairment due to the elimination mechanisms[FDA Label][F4364]. Fluticasone furoate is not associated with carcinogenicity, mutagenicity, or impairment of fertility[FDA Label]. There are no well controlled studies in pregnancy or lactation though animal studies have shown teratogenicity and hypoadrenalism in the offspring of treated mothers and other corticosteroids are known to be excreted in breast milk[FDA Label]. Generally, there are no reported adverse effects with fluticasone in pregnancy[A177127]. Pediatric patients should be given the lowest possible dose and monitored for reduction in growth velocity[FDA Label][A7488]. There is insufficient evidence to determine whether geriatric patients respond differently to other patients[FDA Label]. Systemic exposure may be 27-49% higher in Japanese, Korean, and Chinese patients compared to Caucasian patients[F4364]. Caution should be exercised in these patients and the benefit and risk should be assessed before deciding on a treatment[FDA Label].
DESCRIPTION A synthetic glucocorticoid (glucocorticoid receptor agonist) available as an inhaler and nasal spray for various inflammatory indications. (GtoPdb)
Cell lines
2
Organisms
0
Compound Sets
16
Cayman Chemical Bioactives
29878
ChEMBL Approved Drugs
CHEMBL1676
ChEMBL Drugs
CHEMBL1676
DrugBank
DB08906
DrugBank Approved Drugs
DB08906
DrugCentral
4554
DrugCentral Approved Drugs
4554
DrugMAP
DML72VJ
DrugMAP Approved Drugs
DML72VJ
Guide to Pharmacology
10892
MedChem Express Bioactive Compound Library
HY-15234
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
JS86977WNV
Probe Miner (suitable probes)
P04150/721659
Selleckchem Bioactive Compound Library
fluticasone-furoate
Withdrawn 2.0
EMA16
External IDs
35
Properties
(calculated by RDKit )
Molecular Weight
538.16
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
5
Aromatic Ring Count
1
cLogP
4.93
TPSA
93.81
Fraction CSP3
0.59
Chiral centers
9.0
Largest ring
6.0
QED
0.54
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
ATC
R01AD12
Biosynthetic Origin
Terpenoid (Steroid)
Therapeutic Indication
Antiallergic
Therapeutic Class
Respiratory
Pathway
Immunology/Inflammation
Vitamin D Related/Nuclear Receptor
Target
Glucocorticoid Receptor
Adrenergic Receptor
Source data