Identification

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Name
Fluticasone furoate
Accession Number
DB08906
Type
Small Molecule
Groups
Approved
Description

Fluticasone furoate is a synthetic glucocorticoid available as an inhaler and nasal spray for various inflammatory indicationsLabel8. Fluticasone furoate was first approved in 20077.

Structure
Thumb
Synonyms
  • Fluticasone furoate
  • Fluticasonum furoas
  • Furoate de fluticasone
  • Furoato de fluticasona
External IDs
GSK 685698 / GW-685698X / GW685698X
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2008-10-062011-10-18Eu
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2008-10-062011-10-18Eu
AlisadeSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2008-10-062011-10-18Eu
Arnuity ElliptaPowder100 mcgRespiratory (inhalation)Glaxosmithkline Inc2016-01-26Not applicableCanada
Arnuity ElliptaPowder200 ug/1Respiratory (inhalation)GlaxoSmithKline LLC2014-08-20Not applicableUs
Arnuity ElliptaPowder100 ug/1Respiratory (inhalation)GlaxoSmithKline LLC2014-08-20Not applicableUs
Arnuity ElliptaPowder200 mcgRespiratory (inhalation)Glaxosmithkline Inc2015-12-14Not applicableCanada
Arnuity ElliptaPowder50 ug/1Respiratory (inhalation)GlaxoSmithKline LLC2018-05-17Not applicableUs
AvamysSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2008-01-11Not applicableEu
AvamysSpray, suspension27.5 micrograms/sprayIntrasinalGlaxo Group Limited2008-01-11Not applicableEu
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2017-02-01Not applicableUs
Flonase Sensimist Allergy ReliefSpray, metered27.5 ug/1NasalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2017-07-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2013-08-26Not applicableUs
Breo ElliptaFluticasone furoate (200 mcg) + Vilanterol (25 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2015-10-02Not applicableCanada
Breo ElliptaFluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxo Operations UK Ltd2015-04-302018-01-08Us
Breo ElliptaFluticasone furoate (100 mcg) + Vilanterol (25 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2013-11-29Not applicableCanada
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxo Operations UK Ltd2013-08-262018-01-08Us
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)Remedy Repack2016-04-042016-04-05Us
Breo ElliptaFluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)REMEDYREPACK INC.2019-04-17Not applicableUs
Breo ElliptaFluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2015-04-30Not applicableUs
Breo ElliptaFluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)A-S Medication Solutions2015-04-30Not applicableUs
Trelegy ElliptaFluticasone furoate (100 ug/1) + Umeclidinium bromide (62.5 ug/1) + Vilanterol trifenatate (25 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2017-09-18Not applicableUs
Categories
UNII
JS86977WNV
CAS number
397864-44-7
Weight
Average: 538.576
Monoisotopic: 538.163693965
Chemical Formula
C27H29F3O6S
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,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14-{[(fluoromethyl)sulfanyl]carbonyl}-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-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

Pharmacology

Indication

Fluticasone furoate is indicated as an inhaler for the treatment and management of asthma by prophylaxisLabel8. The fluticasone furoate nasal spray is indicated for treating season and perennial allergic rhinitisLabel4.

Associated Conditions
Pharmacodynamics

Systemically, in vitro experiments show fluticasone furoate activates glucocorticoid receptors, inhibits nuclear factor kappa b, and inhibits lung eosinophilia in ratsLabel8,4.

Mechanism of action

Fluticasone furoate works through an unknown mechanism to affect the action of various cell types and mediators of inflammationLabel8. In vitro experiments show fluticasone furoate activating glucocorticoid receptors, inhibiting nuclear factor kappa b, and inhibiting lung eosinophilia in ratsLabel8,4.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
UProgesterone receptor
agonist
Humans
UMineralocorticoid receptor
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Intranasal exposure of fluticasone furoate results in patients swallowing a larger portion of the doseLabel1. However, absorption is poor and metabolism is high, therefore there is negligible systemic exposure with a nasal bioavailability of 0.50% and oral bioavialability of 1.26%Label5. Inhaled bioavailability is 13.9%8. A study of 24 healthy Caucasian males showed an inhaled bioavailability of 6.3-18.4%5.

Volume of distribution

608L at steady state for intravenous administration of fluticasone furoateLabel. Other reports suggest the mean volume of distribution at steady state is 661L8. A study of 24 healthy Caucasian males showed a volume of distribution at steady state of 704L following intravenous administration5.

Protein binding

Fluticasone furoate is >99%Label protein bound in serum and may be as high as 99.6%8.

Metabolism

Fluticasone furoate is cleared from hepatic metabolism by cytochrome P450 3A4Label8,2. Fluticasone furoate is hydrolysed at the FIVE-S-fluoromethyl carbothioate group, forming an inactive metaboliteLabel1.

Route of elimination

Fluticasone furoate is eliminated ≥90% in the feces and 1-2% in the urineLabel8.

Half life

15.1 hours for intranasal fluticasone furoateLabel and 24 hours for the inhaled formulation8. A study of 24 healthy Caucasian males showed a half life of 13.6 hours following intravenous administration and 17.3-23.9 hours followed inhalation5.

Clearance

57.8L/h for fluticasone furoateLabel. A study of 24 healthy Caucasian males showed a clearance of 71.8L/h following intravenous administration5.

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 studiesLabel6. Fluticasone furoate requires no dosage adjustment in renal impairment but must be used in caution in hepatic impairment due to the elimination mechanismsLabel8. Fluticasone furoate is not associated with carcinogenicity, mutagenicity, or impairment of fertilityLabel. 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 pregnancy3. Pediatric patients should be given the lowest possible dose and monitored for reduction in growth velocityLabel6. There is insufficient evidence to determine whether geriatric patients respond differently to other patientsLabel. Systemic exposure may be 27-49% higher in Japanese, Korean, and Chinese patients compared to Caucasian patients8. Caution should be exercised in these patients and the benefit and risk should be assessed before deciding on a treatmentLabel.

Affected organisms
  • Humans and other mammals
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
(R)-warfarinFluticasone furoate may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinFluticasone furoate may increase the anticoagulant activities of (S)-Warfarin.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Fluticasone furoate.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Fluticasone furoate.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Fluticasone furoate.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Fluticasone furoate.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Fluticasone furoate.
1alpha,24S-Dihydroxyvitamin D2The therapeutic efficacy of 1alpha,24S-Dihydroxyvitamin D2 can be decreased when used in combination with Fluticasone furoate.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Fluticasone furoate.
2,4-thiazolidinedioneThe risk or severity of hyperglycemia can be increased when Fluticasone furoate is combined with 2,4-thiazolidinedione.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

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. [PubMed:2287791]
  2. Harding SM: The human pharmacology of fluticasone propionate. Respir Med. 1990 Nov;84 Suppl A:25-9. [PubMed:2287792]
  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. [PubMed:18047814]
  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. [PubMed:28587510]
  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. [PubMed:23184737]
  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. [PubMed:23578031]
  7. FDA Fluticasone Furoate Approval 2007 [Link]
  8. Fluticasone Furoate (Arnuity Ellipta) FDA Label [File]
External Links
KEGG Drug
D06315
PubChem Compound
9854489
PubChem Substance
175427145
ChemSpider
8030195
BindingDB
50354851
ChEBI
74899
ChEMBL
CHEMBL1676
HET
GW6
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluticasone_furoate
ATC Codes
R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoateR01AD12 — Fluticasone furoateR03AK10 — Vilanterol and fluticasone furoateR03BA09 — Fluticasone furoate
AHFS Codes
  • 52:08.08 — Corticosteroids
PDB Entries
3cld
FDA label
Download (469 KB)
MSDS
Download (309 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAsthma2
1CompletedBasic ScienceAsthma1
1CompletedOtherAsthma1
1CompletedPreventionAsthma / Healthy Volunteers1
1CompletedTreatmentAsthma3
1CompletedTreatmentAsthma / Healthy Volunteers3
1CompletedTreatmentAsthma / Hepatic Impairment1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentAsthma16
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentOesophagitis, Eosinophilic1
2CompletedTreatmentRhinitis, Allergic, Perennial1
2Not Yet RecruitingBasic SciencePharmacokinetics1
2RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentAllergic Rhinitis (AR) / Rhinitis, Allergic, Perennial1
3CompletedTreatmentAllergic Rhinitis (Disorder) / Rhinitis, Allergic, Perennial1
3CompletedTreatmentAsthma18
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)13
3CompletedTreatmentHayfever Allergic Rhinitis Seasonal Rhinitis / Rhinitis, Allergic, Seasonal1
3CompletedTreatmentHayfever / Rhinitis, Allergic, Seasonal / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR) / Rhinitis, Allergic, Perennial4
3CompletedTreatmentPerennial Allergic Rhinitis (PAR) / Rhinitis, Allergic, Perennial and Seasonal / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentPollen Allergy / Rhinitis, Allergic, Seasonal / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentRhinitis1
3CompletedTreatmentRhinitis, Allergic, Perennial2
3CompletedTreatmentRhinitis, Allergic, Perennial / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentRhinitis, Allergic, Seasonal1
3CompletedTreatmentRhinitis, Allergic, Seasonal / Seasonal Allergic Rhinitis (SAR)1
3CompletedTreatmentRhinitis / Rhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis / Rhinitis, Allergic, Seasonal1
3CompletedTreatmentVasomotor Rhinitis2
3WithdrawnTreatmentAsthma1
3WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedNot AvailableRhinitis, Allergic, Perennial1
4CompletedNot AvailableSeasonal Allergic Rhinitis (SAR)1
4CompletedBasic ScienceChildhood Obstructive Sleep Apnea Syndrome (OSAS)1
4CompletedOtherRhinitis, Allergic, Perennial and Seasonal1
4CompletedOtherSeasonal Allergic Rhinitis (SAR)1
4CompletedTreatmentAllergic Conjunctivitis to Tree Pollen or Grass Pollen1
4CompletedTreatmentAllergic Rhinitis (AR)2
4CompletedTreatmentAsthma2
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentRhinitis, Allergic, Perennial3
4CompletedTreatmentRhinitis, Allergic, Perennial / Seasonal Allergic Rhinitis (SAR)2
4CompletedTreatmentRhinitis, Allergic, Seasonal2
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
4RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentAsthma2
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Unknown StatusTreatmentPatients With Nasal Polyps1
4WithdrawnTreatmentAllergic Rhinitis (AR)1
4WithdrawnTreatmentAsthma1
Not AvailableCompletedNot AvailableCognition / Driving Ability / Seasonal Allergic Rhinitis (SAR)1
Not AvailableCompletedNot AvailableRhinitis, Allergic, Perennial and Seasonal1
Not AvailableCompletedNot AvailableRhinitis, Allergic, Perennial / Rhinitis, Allergic, Seasonal1
Not AvailableCompletedTreatmentAllergic Rhinitis (AR)1
Not AvailableRecruitingNot AvailableAsthma1
Not AvailableTerminatedNot AvailableRhinitis, Allergic, Seasonal / Seasonal Allergic Rhinitis (SAR)1
Not AvailableTerminatedTreatmentAsthma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Spray, suspensionIntrasinal27.5 micrograms/spray
PowderRespiratory (inhalation)100 mcg
PowderRespiratory (inhalation)100 ug/1
PowderRespiratory (inhalation)200 ug/1
PowderRespiratory (inhalation)200 mcg
PowderRespiratory (inhalation)50 ug/1
Spray, meteredNasal
PowderRespiratory (inhalation)
Spray, meteredNasal27.5 ug/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5873360Yes1999-02-232016-08-23Us
US6858596No2005-02-222021-08-03Us
US7101866No2006-09-052021-08-03Us
US7541350No2009-06-022021-08-03Us
US8347879No2013-01-082028-07-15Us
US8752543No2014-06-172026-04-05Us
US8062264No2011-11-222026-04-05Us
US8147461No2012-04-032028-10-15Us
US7439393No2008-10-212022-09-11Us
US6759398No2004-07-062021-08-03Us
USRE44874No2014-04-292023-03-23Us
US6537983No2003-03-252021-08-03Us
US8511304No2013-08-202027-06-14Us
US7629335No2009-12-082021-08-03Us
US8161968No2012-04-242028-02-05Us
US8746242No2014-06-102030-10-11Us
US8113199No2012-02-142027-10-23Us
US7776895No2010-08-172022-09-11Us
US8534281No2013-09-172029-08-10Us
US6878698No2005-04-122021-08-03Us
US8309572No2012-11-132025-04-27Us
US8183257No2012-05-222025-07-27Us
US7488827No2009-02-102025-04-27Us
US7498440No2009-03-032025-04-27Us
US8201556No2012-06-192029-02-05Us
US9320862No2016-04-262024-11-06Us
US9333310No2016-05-102027-10-02Us
US9750726No2017-09-052030-11-29Us
US9750762No2017-09-052030-11-29Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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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)13.56ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.81 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity130.08 m3·mol-1ChemAxon
Polarizability51.55 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, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Steroid ester / Androgen-skeleton / Androstane-skeleton / Hydroxysteroid / Halo-steroid / 6-halo-steroid / 9-halo-steroid / Oxosteroid / 11-beta-hydroxysteroid / 11-hydroxysteroid
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)

Targets

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. [PubMed:16507850]
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. [PubMed:16507850]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
Curator comments
Induction likely occurs indirectly via transcriptional modulation via the glucocorticoid receptor.
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. [PubMed:20482443]
  2. FDA reports [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [PubMed:16565171]
  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. [PubMed:20482443]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. [PubMed:16565171]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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. [PubMed:26721703]
  2. FDA reports [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. FDA reports [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. FDA reports [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [PubMed:18694910]
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. FDA reports [Link]

Drug created on June 16, 2013 17:03 / Updated on December 08, 2019 20:10