Fluticasone furoate

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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 indications^Label¹⁹. Fluticasone furoate was first approved in 2007⁷.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

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

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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 Type	Indication	Combined Product Details	Approval Level	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

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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

Target	Actions	Organism
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

Fluticasone furoate
- M10 (GW694301X)
  - M26 fluticasone furoate
- M21 fluticasone furoate

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 milk^Label. 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.

Drug	Interaction
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Abametapir	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

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International/Other Brands

Veramyst

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Alisade	Spray, suspension	27.5 micrograms/spray	Intrasinal	Glaxo Group Limited	2016-09-07	2011-08-26
Alisade	Spray, suspension	27.5 micrograms/spray	Intrasinal	Glaxo Group Limited	2016-09-07	2011-08-26
Alisade	Spray, suspension	27.5 micrograms/spray	Intrasinal	Glaxo Group Limited	2016-09-07	2011-08-26
Arnuity Ellipta	Powder	50 ug/1	Respiratory (inhalation)	Glaxosmithkline Inc	2018-05-17	Not applicable
Arnuity Ellipta	Powder	200 mcg / act	Respiratory (inhalation)	Glaxosmithkline Inc	2015-12-14	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Flonase Sensimist Allergy Relief	Spray, metered	27.5 ug/1	Nasal	Haleon US Holdings LLC	2017-02-01	Not applicable
Flonase Sensimist Allergy Relief	Spray, metered	27.5 ug/1	Nasal	A-S Medication Solutions	2017-02-01	Not applicable
Flonase Sensimist Allergy Relief	Spray, metered	27.5 ug/1	Nasal	Haleon US Holdings LLC	2017-07-01	Not applicable
Flonase Sensimist Allergy Relief	Spray, metered	27.5 ug/1	Nasal	A-S Medication Solutions	2017-02-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Breo Ellipta	Fluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2015-04-30	Not applicable
Breo Ellipta	Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	REMEDYREPACK INC.	2019-04-17	Not applicable
Breo Ellipta	Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	Remedy Repack	2016-04-04	2016-04-05
Breo Ellipta	Fluticasone furoate (100 mcg / act) + Vilanterol trifenatate (25 mcg / act)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2013-11-29	Not applicable
Breo Ellipta	Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2013-08-26	Not applicable

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
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 Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Completed	Not Available	Asthma	2	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Chronic Obstructive Pulmonary Disease (COPD)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Cognitive Functioning / Driving Ability / Seasonal Allergic Rhinitis	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Perennial Allergic Rhinitis (PAR)	1	somestatus	stop reason	just information to hide
Not Available	Completed	Not Available	Rhinitis, Allergic, Perennial and Seasonal	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
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
Spray, suspension	Intrasinal	27.5 micrograms/spray
Suspension		27.5 mcg
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	Nasal	27.5 MICROGRAMMI
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
Spray, metered	Nasal	27.5 ug/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5873360	Yes	1999-02-23	2016-08-23
US6858596	No	2005-02-22	2021-08-03
US7101866	No	2006-09-05	2021-08-03
US7541350	No	2009-06-02	2021-08-03
US8347879	No	2013-01-08	2028-07-15
US8752543	No	2014-06-17	2026-04-05
US8062264	No	2011-11-22	2026-04-05
US8147461	No	2012-04-03	2028-10-15
US7439393	Yes	2008-10-21	2025-11-21
US6759398	No	2004-07-06	2021-08-03
USRE44874	No	2014-04-29	2023-03-23
US6537983	No	2003-03-25	2021-08-03
US8511304	Yes	2013-08-20	2027-12-14
US7629335	No	2009-12-08	2021-08-03
US8161968	Yes	2012-04-24	2028-08-05
US8746242	Yes	2014-06-10	2031-04-11
US8113199	Yes	2012-02-14	2028-04-23
US7776895	No	2010-08-17	2022-09-11
US8534281	Yes	2013-09-17	2030-09-08
US6878698	No	2005-04-12	2021-08-03
US8309572	No	2012-11-13	2025-04-27
US8183257	No	2012-05-22	2025-07-27
US7488827	No	2009-02-10	2025-04-27
US7498440	No	2009-03-03	2025-04-27
US8201556	No	2012-06-19	2029-02-05
US9320862	No	2016-04-26	2024-11-06
US9333310	Yes	2016-05-10	2028-04-02
US9750726	No	2017-09-05	2030-11-29
US9750762	No	2017-09-05	2030-11-29
US11116721	Yes	2021-09-14	2029-08-26
US11090294	No	2021-08-17	2030-11-29

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-02mu-9301640000-cdf6e36809a421d6af63
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a70-0000950000-8b9abe0cd9ad6fb85d67
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-1103890000-4cf417c44a5dcd845d53
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9001000000-9b55943b28de4fa3658e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-9000000000-b826ee1a932652ebca86
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f7c-9533250000-f458b0b359123d1a7d4b

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	0.49	N/A	N/A	A28638
IC 50 (nM)	0.0398	N/A	N/A	A29582

Details1. Glucocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). 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 modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth (By similarity)
Specific Function: core promoter sequence-specific DNA binding
Gene Name: NR3C1
Uniprot ID: P04150
Uniprot Name: Glucocorticoid receptor
Molecular Weight: 85658.57 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Fluticasone Furoate (Veramyst) Nasal Spray FDA Label [File]
Fluticasone Furoate (Arnuity Ellipta) FDA Label [File]

Details2. Progesterone receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General 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. Depending on the isoform, progesterone receptor functions as a transcriptional activator or repressor
Specific Function: ATPase binding
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]

Details3. Mineralocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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 target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Specific Function: DNA-binding transcription factor activity
Gene Name: NR3C2
Uniprot ID: P08235
Uniprot Name: Mineralocorticoid receptor
Molecular Weight: 107080.615 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

Details1. Cytochrome P450 3A4

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: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

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]
FDA Approved Drug Products: Arnuity Ellipta (fluticasone furoate) powder for inhalation [Link]

Details2. Cytochrome P450 3A5

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: A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
Specific Function: aromatase activity
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]

Details3. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
Specific Function: all-trans retinoic acid 18-hydroxylase activity
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57469.95 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]

Details4. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor
Curator comments: Remove L3868 (broken link), replace with L46501

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function: arachidonic acid epoxygenase activity
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

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]
Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Carriers

Details1. Corticosteroid-binding globulin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species
Specific Function: serine-type endopeptidase inhibitor activity
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]

Details2. Albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function: antioxidant activity
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Albumin
Molecular Weight: 69365.94 Da

References

Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Details3. Alpha-1-acid glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
Specific Function: Not Available
Gene Name: ORM1
Uniprot ID: P02763
Uniprot Name: Alpha-1-acid glycoprotein 1
Molecular Weight: 23539.43 Da

References

Fluticasone furoate/vilanterol: Clinical Pharmacology and Biopharmaceutics review [Link]

Transporters

Details1. ATP-dependent translocase ABCB1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Inducer

General Function: Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function: ABC-type xenobiotic transporter activity
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: ATP-dependent translocase ABCB1
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]

Details2. Solute carrier organic anion transporter family member 1B1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
Specific Function: bile acid transmembrane transporter activity
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 October 13, 2024 00:22

Fluticasone furoate

Identification

Structure for Fluticasone furoate (DB08906)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

References

References

References

Carriers

References

References

References

Transporters

References

References