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
Structure for Fluticasone furoate (DB08906)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Asthma •••••••••••• •••••• Used in combination to manage Asthma Combination Product in combination with: Vilanterol (DB09082) •••••••••••• •••••• Used in combination to manage Asthma Combination Product in combination with: Vilanterol (DB09082), Umeclidinium (DB09076) •••••••••••• •••••• Used in combination to manage Copd Combination Product in combination with: Vilanterol (DB09082), Umeclidinium (DB09076) •••••••••••• •••••• Used in combination to manage Copd Combination Product in combination with: Vilanterol (DB09082) •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism AGlucocorticoid receptor agonistHumans UProgesterone receptor agonistHumans UMineralocorticoid receptor antagonistHumans - 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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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Fluticasone furoate can be increased when it is combined with Abametapir. Abatacept The metabolism of Fluticasone furoate can be increased when combined with Abatacept. Acalabrutinib The serum concentration of Fluticasone furoate can be increased when it is combined with Acalabrutinib. Acarbose The risk or severity of hyperglycemia can be increased when Fluticasone furoate is combined with Acarbose. Aceclofenac The risk or severity of gastrointestinal irritation can be increased when Fluticasone furoate is combined with Aceclofenac. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Veramyst
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alisade Spray, suspension 27.5 micrograms/spray Intrasinal Glaxo Group Limited 2016-09-07 2011-10-18 EU 
Alisade Spray, suspension 27.5 micrograms/spray Intrasinal Glaxo Group Limited 2016-09-07 2011-10-18 EU Alisade Spray, suspension 27.5 micrograms/spray Intrasinal Glaxo Group Limited 2016-09-07 2011-10-18 EU Arnuity Ellipta Powder 50 ug/1 Respiratory (inhalation) GlaxoSmithKline LLC 2018-05-17 Not applicable US 
Arnuity Ellipta Powder 200 mcg / act Respiratory (inhalation) Glaxosmithkline Inc 2015-12-14 Not applicable Canada 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Flonase Sensimist Allergy Relief Spray, metered 27.5 ug/1 Nasal GlaxoSmithKline Consumer Healthcare Holdings (US) LLC 2017-02-01 Not applicable US Flonase Sensimist Allergy Relief Spray, metered 27.5 ug/1 Nasal A-S Medication Solutions 2017-02-01 Not applicable US Flonase Sensimist Allergy Relief Spray, metered 27.5 ug/1 Nasal GlaxoSmithKline Consumer Healthcare Holdings (US) LLC 2017-07-01 Not applicable US Flonase Sensimist Allergy Relief Spray, metered 27.5 ug/1 Nasal A-S Medication Solutions 2017-02-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Breo Ellipta Fluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2015-04-30 Not applicable US Breo Ellipta Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1) Powder Respiratory (inhalation) REMEDYREPACK INC. 2019-04-17 Not applicable US Breo Ellipta Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1) Powder Respiratory (inhalation) Remedy Repack 2016-04-04 2016-04-05 US Breo Ellipta Fluticasone furoate (100 mcg / act) + Vilanterol trifenatate (25 mcg / act) Powder Respiratory (inhalation) Glaxosmithkline Inc 2013-11-29 Not applicable Canada Breo Ellipta Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2013-08-26 Not applicable US
Categories
- ATC Codes
- R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoate
- R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R01AD — Corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenal Cortex Hormones
- Agents to Treat Airway Disease
- Androstanes
- Androstenes
- Corticosteroids
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs for Obstructive Airway Diseases
- Fused-Ring Compounds
- Glucocorticoids
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Nasal Preparations
- OATP1B1/SLCO1B1 Inhibitors
- P-glycoprotein inducers
- P-glycoprotein substrates
- Steroids
- Thyroxine-binding globulin inhibitors
- 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
- Phillipps GH: Structure-activity relationships of topically active steroids: the selection of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:19-23. [Article]
- Harding SM: The human pharmacology of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:25-9. [Article]
- 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]
- 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]
- 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]
- 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]
- FDA Fluticasone Furoate Approval 2007 [Link]
- FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation [Link]
- FDA Approved Drug Products: Arnuity Ellipta (fluticasone furoate) powder for inhalation [Link]
- DailyMed: Flonase Sensimist (fluticasone furoate) nasal spray [Link]
- FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation [Link]
- FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation (December 2022) [Link]
- FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation (May 2023) [Link]
- Fluticasone Furoate MSDS [Link]
- Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
- FDA Approved Drug Products: VERAMYST (fluticasone furoate) nasal spray [Link]
- Health Canada Approved Drug Proucts: BREO ELLIPTA (fluticasone furoate/vilantero) dry powder for oral inhalation [Link]
- FDA Approved Drug Products: ARNUITY ELLIPTA (fluticasone furoate inhalation powder), for oral corticosteroids (October 2023) [Link]
- Fluticasone Furoate (Arnuity Ellipta) FDA Label [File]
- External Links
- KEGG Drug
- D06315
- PubChem Compound
- 9854489
- PubChem Substance
- 175427145
- ChemSpider
- 8030195
- BindingDB
- 50354851
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Perennial Allergic Rhinitis (PAR) 1 4 Completed Not Available Seasonal Allergic Rhinitis 1 4 Completed Basic Science Childhood Obstructive Sleep Apnea Syndrome (OSAS) 1 4 Completed Basic Science Chronic Obstructive Pulmonary Disease (COPD) 1 4 Completed Other Rhinitis, Allergic, Perennial and Seasonal 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Spray, suspension Intrasinal 27.5 micrograms/spray Powder Buccal 200.000 mcg Powder Respiratory (inhalation) 100 mcg / act Powder Respiratory (inhalation) 100 ug/1 Powder Respiratory (inhalation) 200 mcg / act Powder Respiratory (inhalation) 200 ug/1 Powder Respiratory (inhalation) 50 ug/1 Powder, metered Respiratory (inhalation) 100 mcg Powder, metered Respiratory (inhalation) 200 mcg Powder Respiratory (inhalation) 100 mcg Powder Respiratory (inhalation) 200 mcg Spray Nasal Spray Nasal 27.5 MCG Spray, metered Nasal 27.5 mcg / act Suspension Spray, suspension Nasal 27.5 mcg/1dose Spray; suspension Nasal 27.5 mcg Spray Nasal 27.5 µg Suspension Nasal 0.500 mg Spray, metered Nasal 27.5 mcg Spray, suspension Nasal 0.0275 mg Suspension Intrasinal; Nasal 27.5 mcg Powder Respiratory (inhalation) Spray, suspension Nasal 27.5 mcg Suspension Nasal; Respiratory (inhalation) 0.055 g Powder, metered Respiratory (inhalation) Powder, metered Respiratory (inhalation) 184 MICROGRAMMI/22MICROGRAMMI Aerosol, powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) Powder Oral; Respiratory (inhalation) Powder Buccal Drug delivery system Buccal Spray, metered Nasal 27.5 ug/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5873360 Yes 1999-02-23 2016-08-23 US US6858596 No 2005-02-22 2021-08-03 US US7101866 No 2006-09-05 2021-08-03 US US7541350 No 2009-06-02 2021-08-03 US US8347879 No 2013-01-08 2028-07-15 US US8752543 No 2014-06-17 2026-04-05 US US8062264 No 2011-11-22 2026-04-05 US US8147461 No 2012-04-03 2028-10-15 US US7439393 Yes 2008-10-21 2025-11-21 US US6759398 No 2004-07-06 2021-08-03 US USRE44874 No 2014-04-29 2023-03-23 US US6537983 No 2003-03-25 2021-08-03 US US8511304 Yes 2013-08-20 2027-12-14 US US7629335 No 2009-12-08 2021-08-03 US US8161968 Yes 2012-04-24 2028-08-05 US US8746242 Yes 2014-06-10 2031-04-11 US US8113199 Yes 2012-02-14 2028-04-23 US US7776895 No 2010-08-17 2022-09-11 US US8534281 Yes 2013-09-17 2030-09-08 US US6878698 No 2005-04-12 2021-08-03 US US8309572 No 2012-11-13 2025-04-27 US US8183257 No 2012-05-22 2025-07-27 US US7488827 No 2009-02-10 2025-04-27 US US7498440 No 2009-03-03 2025-04-27 US US8201556 No 2012-06-19 2029-02-05 US US9320862 No 2016-04-26 2024-11-06 US US9333310 Yes 2016-05-10 2028-04-02 US US9750726 No 2017-09-05 2030-11-29 US US9750762 No 2017-09-05 2030-11-29 US US11116721 Yes 2021-09-14 2029-08-26 US US11090294 No 2021-08-17 2030-11-29 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 250-252 [MSDS] water solubility Insoluble [MSDS] - Predicted Properties
Property Value Source Water Solubility 0.0434 mg/mL ALOGPS logP 3.73 ALOGPS logP 4.13 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 13.61 Chemaxon pKa (Strongest Basic) -3.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 93.81 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 130.08 m3·mol-1 Chemaxon Polarizability 51.56 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9917 Blood Brain Barrier + 0.9666 Caco-2 permeable - 0.5222 P-glycoprotein substrate Substrate 0.7675 P-glycoprotein inhibitor I Inhibitor 0.784 P-glycoprotein inhibitor II Inhibitor 0.604 Renal organic cation transporter Non-inhibitor 0.8329 CYP450 2C9 substrate Non-substrate 0.8023 CYP450 2D6 substrate Non-substrate 0.8893 CYP450 3A4 substrate Substrate 0.7205 CYP450 1A2 substrate Non-inhibitor 0.6493 CYP450 2C9 inhibitor Non-inhibitor 0.7288 CYP450 2D6 inhibitor Non-inhibitor 0.8305 CYP450 2C19 inhibitor Non-inhibitor 0.6388 CYP450 3A4 inhibitor Inhibitor 0.9211 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.69 Ames test Non AMES toxic 0.747 Carcinogenicity Non-carcinogens 0.9079 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6232 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9787 hERG inhibition (predictor II) Non-inhibitor 0.566
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 214.0303 predictedDeepCCS 1.0 (2019) [M+H]+ 216.20912 predictedDeepCCS 1.0 (2019) [M+Na]+ 223.35367 predictedDeepCCS 1.0 (2019)
Targets
- 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
- 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
- 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
- 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
- SubstrateInhibitorInducer
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitorInducer
- 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
- 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]
- 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
- 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
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
- 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
- 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
- Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- 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
- 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]
- 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]
- 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
- Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]
Drug created at June 16, 2013 23:03 / Updated at February 20, 2024 23:55