Fluticasone furoate

Identification

Summary

Fluticasone furoate is an inhaled corticosteroid that can be used as maintenance treatment of asthma and/or chronic obstructive pulmonary disease (COPD) depending on the product. Also available as a nasal spray to manage symptoms of allergic rhinitis.

Brand Names
Arnuity Ellipta, Avamys, Breo Ellipta, Flonase Sensimist, Trelegy Ellipta, Veramyst
Generic Name
Fluticasone furoate
DrugBank Accession Number
DB08906
Background

Fluticasone furoate is a synthetic glucocorticoid available as an inhaler and nasal spray for various inflammatory indicationsLabel19. Fluticasone furoate was first approved in 20077.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 538.576
Monoisotopic: 538.163693965
Chemical Formula
C27H29F3O6S
Synonyms
  • Fluticasone furoate
  • Fluticasonum furoas
  • Furoate de fluticasone
  • Furoato de fluticasona
External IDs
  • GSK 685 698
  • GSK 685698
  • GW-685698X
  • GW685698X

Pharmacology

Indication

Fluticasone furoate is indicated for once-daily maintenance (i.e. prophylactic) treatment of asthma in patients ≥5 years old.9 Fluticasone furoate is available in two combination medications - one in combination with vilanterol and one in combination with both vilanterol and umeclidinium- which are both indicated for the management of chronic obstructive pulmonary disease (COPD) and for the treatment of asthma in patients ≥18 years old for the vilanterol-umeclidinium-fluticasone product and ≥5 years old for the vilanterol-fluticasone product.12,13

Fluticasone furoate is available over the counter as a nasal spray for the symptomatic treatment of hay fever and other upper respiratory allergies in patients ≥2 years old.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAsthma••••••••••••••••••
Used in combination to manageAsthmaCombination Product in combination with: Vilanterol (DB09082)••••••••••••••••••
Used in combination to manageAsthmaCombination Product in combination with: Vilanterol (DB09082), Umeclidinium (DB09076)••••••••••••••••••
Used in combination to manageCopdCombination Product in combination with: Vilanterol (DB09082), Umeclidinium (DB09076)••••••••••••••••••
Used in combination to manageCopdCombination Product in combination with: Vilanterol (DB09082)••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Fluticasone furoate is a synthetic trifluorinated corticosteroid with anti-inflammatory activity. Though effective for the treatment of asthma, corticosteroids may not affect symptoms immediately. Individual patients will experience a variable time to onset and degree of symptom relief. Maximum benefit may not be achieved for 1 to 2 weeks or longer after starting treatment. When corticosteroids are discontinued, asthma stability may persist for several days or longer.9

Trials in subjects with asthma have shown a favorable ratio between topical anti-inflammatory activity and systemic corticosteroid effects with recommended doses of orally inhaled fluticasone furoate. This is explained by a combination of a relatively high local anti-inflammatory effect, negligible oral systemic bioavailability (approximately 1.3%), and the minimal pharmacological activity of the metabolites detected in man.9

Inhaled fluticasone furoate at repeat doses of up to 400 mcg in healthy subjects was not associated with statistically significant decreases in serum or urinary cortisol in healthy subjects. Reductions in serum and urine cortisol levels were observed at fluticasone furoate exposures several-fold higher than exposures observed at the therapeutic dose. For subjects with asthma, a randomized, double-blind, parallel-group trial in 104 pediatric subjects showed no difference between once-daily treatment with 50 mcg fluticasone compared with placebo on serum cortisol weighted mean (0 to 24 hours) and serum cortisol AUC(0-24) following 6 weeks of treatment.9

A randomized, double-blind, parallel-group trial in 185 subjects with asthma aged 12 to 65 years showed no difference between once-daily treatment with fluticasone furoate/vilanterol 100 mcg/25 mcg or fluticasone furoate/vilanterol 200 mcg/25 mcg compared with placebo on serum cortisol weighted mean (0 to 24 hours), serum cortisol AUC(0-24), and 24-hour urinary cortisol after 6 weeks of treatment, whereas prednisolone 10 mg given once daily for 7 days resulted in significant cortisol suppression.9

A QT/QTc trial did not demonstrate an effect of fluticasone furoate administration on the QTc interval. The effect of a single dose of 4,000 mcg of orally inhaled fluticasone furoate on the QTc interval was evaluated over 24 hours in 40 healthy male and female subjects in a placebo and positive-controlled (a single dose of 400 mg oral moxifloxacin) cross-over trial. The QTcF maximal mean change from baseline following fluticasone furoate was similar to that observed with placebo with a treatment difference of 0.788 msec (90% CI: -1.802, 3.378). In contrast, moxifloxacin given as a 400-mg tablet resulted in prolongation of the QTcF maximal mean change from baseline compared with placebo with a treatment difference of 9.929 msec (90% CI: 7.339, 12.520).9

Mechanism of action

Fluticasone furoate has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor that is approximately 29.9 times that of dexamethasone and 1.7 times that of fluticasone propionate. The clinical relevance of these findings is unknown.9

The precise mechanism through which fluticasone furoate affects asthma symptoms is not known. Inflammation is an important component in the pathogenesis of asthma. Corticosteroids have been shown to have a wide range of actions on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, cytokines) involved in inflammation. Specific effects of fluticasone furoate demonstrated in in vitro and in vivo models included activation of the glucocorticoid response element, inhibition of pro-inflammatory transcription factors such as NFkB, and inhibition of antigen-induced lung eosinophilia in sensitized rats.4,9 These anti-inflammatory actions of corticosteroids may contribute to their efficacy.9

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
UProgesterone receptor
agonist
Humans
UMineralocorticoid receptor
antagonist
Humans
Absorption

Fluticasone furoate plasma levels may not predict therapeutic effect. Peak plasma concentrations are reached within 0.5 to 1 hour. Absolute bioavailability of fluticasone furoate when administrated by inhalation was 13.9%, primarily due to absorption of the inhaled portion of the dose delivered to the lung. Oral bioavailability from the swallowed portion of the dose is low (approximately 1.3%) due to extensive first-pass metabolism. Systemic exposure (AUC) in subjects with asthma was 26% lower than observed in healthy subjects.9 Following repeat dosing of inhaled fluticasone furoate, steady state was achieved within 6 days with up to 2.6-fold accumulation.12 Intranasal exposure of fluticasone furoate also results in patients swallowing a larger portion of the dose.1

Volume of distribution

Following intravenous administration to healthy subjects, the mean volume of distribution at steady state was 661 L.9,12,13 A study of 24 healthy Caucasian males showed a volume of distribution at steady state of 704L following intravenous administration.5

Protein binding

Fluticasone furoate is >99% protein bound in serum and may be as high as 99.6%, predominantly to albumin (96%) and α1-acid glycoprotein (90%).9,12,13,15

Metabolism

Fluticasone furoate is cleared from systemic circulation principally by hepatic metabolism via CYP3A4 to metabolites with significantly reduced corticosteroid activity. There was no in vivo evidence for cleavage of the furoate moiety resulting in the formation of fluticasone.9,12,13,2 Fluticasone furoate is also hydrolyzed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metabolite.1

Hover over products below to view reaction partners

Route of elimination

Following intravenous dosing with radiolabeled fluticasone furoate, mass balance showed 90% of radiolabel in the feces and 2% in the urine. Following oral dosing, radiolabel recovered in feces was 101% of the total dose, and that in urine was approximately 1% of the total dose.12

Half-life

Following repeat-dose inhaled administration, the plasma elimination phase half-life averaged 24 hours.9,12,13 A study of 24 healthy Caucasian males showed a half-life of 13.6 hours following intravenous administration and 17.3-23.9 hours following inhalation.5

Clearance

Following intravenous administration to healthy subjects, fluticasone furoate was cleared from systemic circulation principally by hepatic metabolism via CYP3A4 with a total plasma clearance of 65.4 L/hr.17 A study of 24 healthy Caucasian males also showed a clearance of 71.8L/h following intravenous administration.5

Adverse Effects
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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.9,12,13,6 Fluticasone furoate requires no dosage adjustment in renal impairment but must be used with caution in hepatic impairment due to the elimination mechanisms.9,12,13 Fluticasone furoate is not associated with carcinogenicity, mutagenicity, or impairment of fertility.9,12,13 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 milkLabel. Generally, there are no reported adverse effects with fluticasone in pregnancy.3 Pediatric patients should be given the lowest possible dose and monitored for a reduction in growth velocity.9,12,13,6 There is insufficient evidence to determine whether geriatric patients respond differently to other patients.9,12,13 Systemic exposure may be 27-49% higher in Japanese, Korean, and Chinese patients compared to Caucasian patients.9,12,13 Caution should be exercised in these patients and the benefit and risk should be assessed before deciding on a treatment.9,12,13

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Fluticasone furoate can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Fluticasone furoate can be increased when combined with Abatacept.
AcalabrutinibThe serum concentration of Fluticasone furoate can be increased when it is combined with Acalabrutinib.
AcarboseThe risk or severity of hyperglycemia can be increased when Fluticasone furoate is combined with Acarbose.
AceclofenacThe risk or severity of gastrointestinal irritation can be increased when Fluticasone furoate is combined with Aceclofenac.
Food Interactions
No interactions found.

Products

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International/Other Brands
Veramyst
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2016-09-072011-10-18EU flag
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2016-09-072011-10-18EU flag
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2016-09-072011-10-18EU flag
Arnuity ElliptaPowder200 ug/1Respiratory (inhalation)GlaxoSmithKline LLC2014-08-20Not applicableUS flag
Arnuity ElliptaPowder100 mcg / actRespiratory (inhalation)Glaxosmithkline Inc2016-01-26Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalA-S Medication Solutions2017-02-01Not applicableUS flag
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalHaleon US Holdings LLC2017-07-01Not applicableUS flag
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalA-S Medication Solutions2017-02-01Not applicableUS flag
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2017-02-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2013-08-26Not applicableUS flag
Breo ElliptaFluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxo Operations UK Ltd2015-04-302018-01-08US flag
Breo ElliptaFluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)A-S Medication Solutions2015-04-30Not applicableUS flag
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxo Operations UK Ltd2013-08-262018-01-08US flag
Breo ElliptaFluticasone furoate (50 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2023-05-12Not applicableUS flag

Categories

ATC Codes
R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoateR01AD12 — Fluticasone furoateR03AK10 — Vilanterol and fluticasone furoateR03BA09 — Fluticasone furoate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Furoic acid esters / Heteroaromatic compounds / Thioesters / Secondary alcohols / Carbothioic S-esters
show 11 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Alcohol / Alkyl fluoride / Alkyl halide / Androgen-skeleton
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
thioester, 11beta-hydroxy steroid, steroid ester, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, corticosteroid, 2-furoate ester (CHEBI:74899)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
JS86977WNV
CAS number
397864-44-7
InChI Key
XTULMSXFIHGYFS-VLSRWLAYSA-N
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
IUPAC Name
(1R,2R,3aS,3bS,5S,9aS,9bR,10S,11aS)-5,9b-difluoro-1-{[(fluoromethyl)sulfanyl]carbonyl}-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl furan-2-carboxylate
SMILES
[H][C@@]12C[C@@H](C)[C@](OC(=O)C3=CC=CO3)(C(=O)SCF)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

References

Synthesis Reference

Adrienne KOVACSNE-MEZEI, Roman Gabriel, Alexandr Jegorov, "POLYMORPHS OF FLUTICASONE FUROATE AND PROCESSES FOR PREPARATION THEREOF." U.S. Patent US20100240629, issued September 23, 2010.

US20100240629
General References
  1. Phillipps GH: Structure-activity relationships of topically active steroids: the selection of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:19-23. [Article]
  2. Harding SM: The human pharmacology of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:25-9. [Article]
  3. Choi JS, Han JY, Kim MY, Velazquez-Armenta EY, Nava-Ocampo AA: Pregnancy outcomes in women using inhaled fluticasone during pregnancy: a case series. Allergol Immunopathol (Madr). 2007 Nov-Dec;35(6):239-42. [Article]
  4. Spadijer Mirkovic C, Peric A, Vukomanovic Durdevic B, Vojvodic D: Effects of Fluticasone Furoate Nasal Spray on Parameters of Eosinophilic Inflammation in Patients With Nasal Polyposis and Perennial Allergic Rhinitis. Ann Otol Rhinol Laryngol. 2017 Aug;126(8):573-580. doi: 10.1177/0003489417713505. Epub 2017 Jun 6. [Article]
  5. Allen A, Bareille PJ, Rousell VM: Fluticasone furoate, a novel inhaled corticosteroid, demonstrates prolonged lung absorption kinetics in man compared with inhaled fluticasone propionate. Clin Pharmacokinet. 2013 Jan;52(1):37-42. doi: 10.1007/s40262-012-0021-x. [Article]
  6. Allen A, Schenkenberger I, Trivedi R, Cole J, Hicks W, Gul N, Jacques L: Inhaled fluticasone furoate/vilanterol does not affect hypothalamic-pituitary-adrenal axis function in adolescent and adult asthma: randomised, double-blind, placebo-controlled study. Clin Respir J. 2013 Oct;7(4):397-406. doi: 10.1111/crj.12026. Epub 2013 Jun 5. [Article]
  7. FDA Fluticasone Furoate Approval 2007 [Link]
  8. FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation [Link]
  9. FDA Approved Drug Products: Arnuity Ellipta (fluticasone furoate) powder for inhalation [Link]
  10. DailyMed: Flonase Sensimist (fluticasone furoate) nasal spray [Link]
  11. FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation [Link]
  12. FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation (December 2022) [Link]
  13. FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation (May 2023) [Link]
  14. Fluticasone Furoate MSDS [Link]
  15. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
  16. FDA Approved Drug Products: VERAMYST (fluticasone furoate) nasal spray [Link]
  17. Health Canada Approved Drug Proucts: BREO ELLIPTA (fluticasone furoate/vilantero) dry powder for oral inhalation [Link]
  18. FDA Approved Drug Products: ARNUITY ELLIPTA (fluticasone furoate inhalation powder), for oral corticosteroids (October 2023) [Link]
  19. Fluticasone Furoate (Arnuity Ellipta) FDA Label [File]
KEGG Drug
D06315
PubChem Compound
9854489
PubChem Substance
175427145
ChemSpider
8030195
BindingDB
50354851
RxNav
705022
ChEBI
74899
ChEMBL
CHEMBL1676
ZINC
ZINC000003992105
PDBe Ligand
GW6
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluticasone_furoate
PDB Entries
3cld / 7prv
FDA label
Download (469 KB)
MSDS
Download (309 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailablePerennial Allergic Rhinitis (PAR)1
4CompletedNot AvailableSeasonal Allergic Rhinitis1
4CompletedBasic ScienceChildhood Obstructive Sleep Apnea Syndrome (OSAS)1
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4CompletedOtherRhinitis, Allergic, Perennial and Seasonal1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderBuccal200.000 mcg
PowderRespiratory (inhalation)100 mcg / act
PowderRespiratory (inhalation)100 ug/1
PowderRespiratory (inhalation)200 ug/1
PowderRespiratory (inhalation)200 mcg / act
PowderRespiratory (inhalation)50 ug/1
Powder, meteredRespiratory (inhalation)100 mcg
Powder, meteredRespiratory (inhalation)200 mcg
PowderRespiratory (inhalation)100 mcg
PowderRespiratory (inhalation)200 mcg
SprayNasal
SprayNasal27.5 MCG
Spray, meteredNasal27.5 mcg / act
Spray, suspensionIntrasinal27.5 micrograms/spray
Suspension
Spray, suspensionNasal27.5 mcg/1dose
Spray; suspensionNasal27.5 mcg
SprayNasal27.5 µg
SuspensionNasal0.500 mg
Spray, meteredNasal27.5 mcg
Spray, suspensionNasal0.0275 mg
SuspensionIntrasinal; Nasal27.5 mcg
PowderRespiratory (inhalation)
Spray, suspensionNasal27.5 mcg
SuspensionNasal; Respiratory (inhalation)0.055 g
Powder, meteredRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)184 MICROGRAMMI/22MICROGRAMMI
Aerosol, powderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
PowderOral; Respiratory (inhalation)
PowderBuccal
Drug delivery systemBuccal
Spray, meteredNasal27.5 ug/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5873360Yes1999-02-232016-08-23US flag
US6858596No2005-02-222021-08-03US flag
US7101866No2006-09-052021-08-03US flag
US7541350No2009-06-022021-08-03US flag
US8347879No2013-01-082028-07-15US flag
US8752543No2014-06-172026-04-05US flag
US8062264No2011-11-222026-04-05US flag
US8147461No2012-04-032028-10-15US flag
US7439393Yes2008-10-212025-11-21US flag
US6759398No2004-07-062021-08-03US flag
USRE44874No2014-04-292023-03-23US flag
US6537983No2003-03-252021-08-03US flag
US8511304Yes2013-08-202027-12-14US flag
US7629335No2009-12-082021-08-03US flag
US8161968Yes2012-04-242028-08-05US flag
US8746242Yes2014-06-102031-04-11US flag
US8113199Yes2012-02-142028-04-23US flag
US7776895No2010-08-172022-09-11US flag
US8534281Yes2013-09-172030-09-08US flag
US6878698No2005-04-122021-08-03US flag
US8309572No2012-11-132025-04-27US flag
US8183257No2012-05-222025-07-27US flag
US7488827No2009-02-102025-04-27US flag
US7498440No2009-03-032025-04-27US flag
US8201556No2012-06-192029-02-05US flag
US9320862No2016-04-262024-11-06US flag
US9333310Yes2016-05-102028-04-02US flag
US9750726No2017-09-052030-11-29US flag
US9750762No2017-09-052030-11-29US flag
US11116721Yes2021-09-142029-08-26US flag
US11090294No2021-08-172030-11-29US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)250-252[MSDS]
water solubilityInsoluble [MSDS]
Predicted Properties
PropertyValueSource
Water Solubility0.0434 mg/mLALOGPS
logP3.73ALOGPS
logP4.13Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.61Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area93.81 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity130.08 m3·mol-1Chemaxon
Polarizability51.56 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9917
Blood Brain Barrier+0.9666
Caco-2 permeable-0.5222
P-glycoprotein substrateSubstrate0.7675
P-glycoprotein inhibitor IInhibitor0.784
P-glycoprotein inhibitor IIInhibitor0.604
Renal organic cation transporterNon-inhibitor0.8329
CYP450 2C9 substrateNon-substrate0.8023
CYP450 2D6 substrateNon-substrate0.8893
CYP450 3A4 substrateSubstrate0.7205
CYP450 1A2 substrateNon-inhibitor0.6493
CYP450 2C9 inhibitorNon-inhibitor0.7288
CYP450 2D6 inhibitorNon-inhibitor0.8305
CYP450 2C19 inhibitorNon-inhibitor0.6388
CYP450 3A4 inhibitorInhibitor0.9211
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.69
Ames testNon AMES toxic0.747
CarcinogenicityNon-carcinogens0.9079
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6232 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9787
hERG inhibition (predictor II)Non-inhibitor0.566
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02mu-9301640000-cdf6e36809a421d6af63
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a70-0000950000-8b9abe0cd9ad6fb85d67
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1103890000-4cf417c44a5dcd845d53
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9001000000-9b55943b28de4fa3658e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-b826ee1a932652ebca86
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7c-9533250000-f458b0b359123d1a7d4b
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.0303
predicted
DeepCCS 1.0 (2019)
[M+H]+216.20912
predicted
DeepCCS 1.0 (2019)
[M+Na]+223.35367
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Glucocorticoid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Fluticasone Furoate (Veramyst) Nasal Spray FDA Label [File]
  2. Fluticasone Furoate (Arnuity Ellipta) FDA Label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Issar M, Sahasranaman S, Buchwald P, Hochhaus G: Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids. Eur Respir J. 2006 Mar;27(3):511-6. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Inducer
Curator comments
Induction likely occurs indirectly via transcriptional modulation via the glucocorticoid receptor. Remove L3868 (broken link), replace with L46501
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
  2. FDA Approved Drug Products: Arnuity Ellipta (fluticasone furoate) powder for inhalation [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Inducer
Curator comments
Induction likely occurs indirectly via transcriptional modulation via the glucocorticoid receptor.
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [Article]
  2. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Pearce RE, Leeder JS, Kearns GL: Biotransformation of fluticasone: in vitro characterization. Drug Metab Dispos. 2006 Jun;34(6):1035-40. Epub 2006 Mar 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Remove L3868 (broken link), replace with L46501
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
  2. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Gardill BR, Vogl MR, Lin HY, Hammond GL, Muller YA: Corticosteroid-binding globulin: structure-function implications from species differences. PLoS One. 2012;7(12):e52759. doi: 10.1371/journal.pone.0052759. Epub 2012 Dec 26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Hughes SC, Shardlow PC, Hollis FJ, Scott RJ, Motivaras DS, Allen A, Rousell VM: Metabolism and disposition of fluticasone furoate, an enhanced-affinity glucocorticoid, in humans. Drug Metab Dispos. 2008 Nov;36(11):2337-44. doi: 10.1124/dmd.108.022137. Epub 2008 Aug 11. [Article]
  2. Crowe A, Tan AM: Oral and inhaled corticosteroids: differences in P-glycoprotein (ABCB1) mediated efflux. Toxicol Appl Pharmacol. 2012 May 1;260(3):294-302. doi: 10.1016/j.taap.2012.03.008. Epub 2012 Mar 23. [Article]
  3. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Drug created at June 16, 2013 23:03 / Updated at March 18, 2024 16:48