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Identification
NameFluticasone Propionate
Accession NumberDB00588  (APRD00065)
TypeSmall Molecule
GroupsApproved
Description

Fluticasone propionate, a medium-potency synthetic corticosteroid, is used topically to relieve inflammatory and pruritic symptoms of dermatoses and psoriasis, intranasally to manage symptoms of allergic and non-allergic rhinitis, and orally for the treatment of asthma. Fluticasone proprionate is marketed under several different brand names such as Flonase®. Fluticasone propionate is also available as a combination product of azelastine hydrochloride and fluticasone propionate called Dymista™. Dymista™ is indicated in patients over 12 years old for symptomatic relief of seasonal allergic rhinitis.

Structure
Thumb
Synonyms
Cutivate
Fluticason
Fluticasona
Fluticasone
Fluticasone propionate
Fluticasonum
External Identifiers
  • CCI 18781
  • GW 685698X
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cutivatecream0.05 %topicalGlaxosmithkline Inc2004-11-082013-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Cutivatelotion.5 mg/mLtopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2009-10-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivateointment.05 mg/gtopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2009-12-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivatecream.5 mg/gtopicalPharma Derm A Division Of Fougera Pharmaceuticals Inc.1990-12-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivatelotion.5 mg/mLtopicalPharma Derm, A Division Of Nycomed Us Inc.2009-10-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flonasespray, metered50 ug/1nasalREMEDYREPACK INC.2013-06-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flonasespray, metered50 ug/1nasalGlaxo Smith Kline Llc1994-11-082016-02-28Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flonase - Aem-sus Nas 50mcg/mdmetered-dose pump50 mcgnasalGlaxosmithkline Inc1993-03-12Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flonase Aem-sus 50mcg/aemmetered-dose aerosol; suspension50 mcgnasalGlaxo Canada Inc1993-12-311998-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flonase Allergy Aqueous Nasal Spraymetered-dose pump50 mcgnasalGlaxosmithkline IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Diskuspowder500 mcginhalationGlaxosmithkline Inc1998-04-02Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Diskuspowder, metered100 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2008-10-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent Diskuspowder50 mcginhalationGlaxosmithkline Inc1998-04-022015-10-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Diskuspowder250 mcginhalationGlaxosmithkline Inc1998-04-02Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Diskuspowder, metered250 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2008-10-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent Diskuspowder100 mcginhalationGlaxosmithkline Inc1998-04-02Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Diskuspowder, metered50 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2007-05-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered44 ug/1respiratory (inhalation)Physicians Total Care, Inc.2009-02-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAmetered-dose aerosol250 mcginhalation; oralGlaxosmithkline Inc2001-12-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent HFAaerosol, metered220 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2007-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered110 ug/1respiratory (inhalation)Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-01-29Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAmetered-dose aerosol125 mcginhalation; oralGlaxosmithkline Inc2001-12-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent HFAaerosol, metered110 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2007-01-29Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAmetered-dose aerosol50 mcginhalation; oralGlaxosmithkline Inc2001-12-20Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent HFAaerosol, metered44 ug/1respiratory (inhalation)Glaxo Smith Kline Llc2007-04-06Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered220 ug/1respiratory (inhalation)Physicians Total Care, Inc.2006-07-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered110 ug/1respiratory (inhalation)Physicians Total Care, Inc.2005-07-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent Inhalers - Aem Inh-orl 125mcg/aemmetered-dose aerosol125 mcginhalation; oralGlaxosmithkline Inc1998-08-182003-06-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers - Aem Inh-orl 250mcg/aemmetered-dose aerosol250 mcginhalation; oralGlaxosmithkline Inc1998-09-212003-03-27Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers - Aem Inh-orl 25mcg/aemmetered-dose aerosol25 mcginhalation; oralGlaxosmithkline Inc1998-11-272003-06-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers - Aem Inh-orl 50mcg/aemmetered-dose aerosol50 mcginhalation; oralGlaxosmithkline Inc1998-04-092003-06-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers-aem Inh-orl 25mcg/actuationmetered-dose aerosol25 mcginhalation; oralGlaxo Canada Inc1995-12-311999-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers-aem Inh-orl 50mcg/actuationmetered-dose aerosol50 mcginhalation; oralGlaxo Canada Inc1995-12-311998-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers-aem Inh-orl125mcg/actuationmetered-dose aerosol125 mcginhalation; oralGlaxo Canada Inc1995-12-311999-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flovent Inhalers-aem Inh-orl250mcg/actuationmetered-dose aerosol250 mcginhalation; oralGlaxo Canada Inc1995-12-311999-08-12Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Floventhfa HFAaerosol, metered44 ug/1respiratory (inhalation)REMEDYREPACK INC.2013-06-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatelotion.5 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2009-10-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Nu-fluticasonespray, metered dose50 mcgnasalNu Pharm IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ratio-fluticasonemetered-dose pump50 mcgnasalTeva Canada Limited2007-06-07Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fluticasonespray, metered dose50 mcgnasalApotex Inc2007-07-05Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Fluticasonespray, metered50 ug/1nasalMorton Grove Pharmaceuticals, Inc.2012-01-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasonespray, metered50 ug/1nasalMedsource Pharmaceuticals2012-01-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasonespray, metered50 ug/1nasalDIRECT RX2014-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalREMEDYREPACK INC.2013-06-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalRoxane Laboratories, Inc2006-02-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalApotex Corp.2007-09-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalRebel Distributors Corp2008-01-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalPreferred Pharmaceuticals, Inc2012-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalUnit Dose Services2008-01-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalBlenheim Pharmacal, Inc.2007-09-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalPreferred Pharmaceuticals, Inc.2013-04-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalHi Tech Pharmacal Co., Inc.2008-01-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalGolden State Medical Supply, Inc.2011-06-02Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalGW Laboratories, Inc2006-05-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatelotion.5 mg/mLtopicalGlenmark Pharmaceuticals Inc., Usa2011-10-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalClinical Solutions Wholesale2008-01-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalG&W Laboratories, Inc.2006-06-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalProficient Rx LP2008-01-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalPhysicians Total Care, Inc.2006-03-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-05-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalDIRECT RX2014-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatelotion.5 mg/mLtopicalPerrigo New York Inc2013-08-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalPhysicians Total Care, Inc.2005-10-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-05-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalPerrigo New York Inc2006-09-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalREMEDYREPACK INC.2013-06-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalPhysicians Total Care, Inc.2006-09-13Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2004-05-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/1nasalApotex Corp.2007-09-19Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalPerrigo New York Inc2007-07-09Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-06-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
TicanasekitPure Tek Corporation2016-01-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flonase Allergy Reliefspray, metered50 ug/1nasalGlaxo Smith Kline Consumer Healthcare Lp2014-12-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
EzicasIntas
FlixonaseGlaxoSmithKline
FlixotideGlaxoSmithKline
FloventGlaxoSmithKline
FLOVENTHFANot Available
FlunaseGlaxoSmithKline
NasofanTeva
PirinaseGlaxoSmithKline
SeretideGlaxoSmithKline
Brand mixtures
NameLabellerIngredients
Advair 100 DiskusGlaxosmithkline Inc
Advair 125Glaxosmithkline Inc
Advair 250Glaxosmithkline Inc
Advair 250 DiskusGlaxosmithkline Inc
Advair 500 DiskusGlaxosmithkline Inc
Advair DiskusGlaxo Smith Kline Llc
Advair HFAGlaxo Smith Kline Llc
Advairdiskus DiskusREMEDYREPACK INC.
DymistaMeda Pharmaceuticals Inc.
SaltsNot Available
CategoriesNot Available
UNIIO2GMZ0LF5W
CAS number80474-14-2
WeightAverage: 500.571
Monoisotopic: 500.184429407
Chemical FormulaC25H31F3O5S
InChI KeyInChIKey=WMWTYOKRWGGJOA-CENSZEJFSA-N
InChI
InChI=1S/C25H31F3O5S/c1-5-20(31)33-25(21(32)34-12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15+,16+,18+,19+,22+,23+,24+,25+/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 propanoate
SMILES
[H][C@@]12C[C@@H](C)[C@](OC(=O)CC)(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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Carboxylic acid ester
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Halomethane
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFluticasone propionate, a medium-potency synthetic corticosteroid, is used topically to relieve inflammatory and pruritic symptoms of dermatoses and psoriasis, intranasally to manage symptoms of allergic and non-allergic rhinitis, and orally for the maintenance treatment of asthma as prophylactic therapy and for patients requiring oral corticosteroid therapy for asthma.
PharmacodynamicsFluticasone is an extremely potent vasoconstrictor and anti-inflammatory agent. Its effectiveness in inhaled forms is due to its direct local effect.
Mechanism of actionBinds to the glucocorticoid receptor. Unbound corticosteroids cross the membranes of cells such as mast cells and eosinophils, binding with high affinity to glucocorticoid receptors (GR). The results include alteration of transcription and protein synthesis, a decreased release of leukocytic acid hydrolases, reduction in fibroblast proliferation, prevention of macrophage accumulation at inflamed sites, reduction of collagen deposition, interference with leukocyte adhesion to the capillary wall, reduction of capillary membrane permeability and subsequent edema, reduction of complement components, inhibition of histamine and kinin release, and interference with the formation of scar tissue. In the management of asthma, the glucocorticoid receptor complexes down-regulates proinflammatory mediators such as interleukin-(IL)-1, 3, and 5, and up-regulates anti-inflammatory mediators such as IkappaB [inhibitory molecule for nuclear factor kappaB1], IL-10, and IL-12. The antiinflammatory actions of corticosteroids are also thought to involve inhibition of cytosolic phospholipase A2 (through activation of lipocortin-1 (annexin)) which controls the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
AbsorptionThe extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Bioavailability, intranasal = <2%; Oral bioavailability is negligible and the major circulating entity is an inactive metabolite.
Volume of distribution

IV administration = 4.2 L/kg

Protein binding91%
Metabolism

Fluticasone propionate is metabolized in the liver by cytochrome P450 3A4-mediated hydrolysis of the 5-fluoromethyl carbothioate grouping. This transformation occurs in 1 metabolic step to produce the inactive 17-(beta)-carboxylic acid metabolite, the only known metabolite detected in man.

SubstrateEnzymesProduct
Fluticasone Propionate
fluticasone 17beta-carboxylic acidDetails
Route of eliminationLess than 5% of the oral dose was excreted in the urine as metabolites. The rest of the dose is excreted in the feces and parent drug and metabolites.
Half lifeTerminal elimination half-life = 7.8 hours
Clearance

The total blood clearance of fluticasone propionate is high (average, 1,093 mL/min), with renal clearance accounting for less than 0.02% of the total.

ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.9701
Caco-2 permeable+0.5417
P-glycoprotein substrateSubstrate0.7099
P-glycoprotein inhibitor IInhibitor0.7192
P-glycoprotein inhibitor IINon-inhibitor0.8636
Renal organic cation transporterNon-inhibitor0.8689
CYP450 2C9 substrateNon-substrate0.868
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.8988
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.798
CarcinogenicityNon-carcinogens0.8901
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.99
hERG inhibition (predictor II)Non-inhibitor0.6125
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Glaxo group ltd dba glaxosmithkline
  • Altana inc
  • G and w laboratories inc
  • Kv pharmaceutical co
  • Perrigo new york inc
  • Tolmar inc
  • Nycomed us inc
  • Taro pharmaceutical industries ltd
  • Apotex inc richmond hill
  • Hi tech pharmacal co inc
  • Roxane laboratories inc
Packagers
Dosage forms
FormRouteStrength
Powderinhalation
Aerosol, metered doseinhalation
Powderoral; respiratory (inhalation)
Powderrespiratory (inhalation)
Aerosol, meteredrespiratory (inhalation)
Spray, metered dosenasal50 mcg
Creamtopical0.05 %
Spray, meterednasal
Spray, metered dosenasal
Metered-dose pumpnasal50 mcg
Metered-dose aerosol; suspensionnasal50 mcg
Powderinhalation100 mcg
Powderinhalation250 mcg
Powderinhalation50 mcg
Powderinhalation500 mcg
Powder, meteredrespiratory (inhalation)100 ug/1
Powder, meteredrespiratory (inhalation)250 ug/1
Powder, meteredrespiratory (inhalation)50 ug/1
Aerosol, meteredrespiratory (inhalation)110 ug/1
Aerosol, meteredrespiratory (inhalation)220 ug/1
Aerosol, meteredrespiratory (inhalation)44 ug/1
Metered-dose aerosolinhalation; oral125 mcg
Metered-dose aerosolinhalation; oral250 mcg
Metered-dose aerosolinhalation; oral50 mcg
Metered-dose aerosolinhalation; oral25 mcg
Creamtopical.5 mg/g
Lotiontopical.5 mg/mL
Ointmenttopical.05 mg/g
Spray, meterednasal50 ug/.1g
Spray, meterednasal50 ug/1
Kit
Prices
Unit descriptionCostUnit
Fluticasone propionate powder1500.0USD g
Cutivate 0.05% Lotion 120ml Bottle454.6USD bottle
Advair Diskus 60 500-50 mcg/dose Aerosol Disp Pack328.14USD disp
Advair Diskus 60 250-50 mcg/dose Aerosol Disp Pack249.48USD disp
Flovent HFA 220 mcg/act Aerosol 12 gm Inhaler237.67USD inhaler
Cutivate 0.05% Cream 60 gm Tube217.11USD tube
Advair Diskus 60 100-50 mcg/dose Aerosol Disp Pack200.79USD disp
Advair Diskus 14 500-50 mcg/dose Aerosol Disp Pack156.64USD disp
Flovent HFA 110 mcg/act Aerosol 12 gm Inhaler153.01USD inhaler
Cutivate 0.005% Ointment 60 gm Tube128.28USD tube
Flovent HFA 44 mcg/act Aerosol 10.6 gm Inhaler114.27USD inhaler
Flovent Diskus 60 50 mcg/blist Aerosol Inhaler104.74USD inhaler
Flonase 50 mcg/act Suspension 16 gm Bottle94.59USD bottle
Fluticasone Propionate 50 mcg/act Suspension 16 gm Bottle78.28USD bottle
Cutivate 0.05% Cream 30 gm Tube62.99USD tube
Fluticasone Propionate 0.005% Ointment 60 gm Tube56.27USD tube
Fluticasone Propionate 0.05% Cream 60 gm Tube56.27USD tube
Cutivate 0.005% Ointment 30 gm Tube44.99USD tube
Fluticasone Propionate 0.005% Ointment 30 gm Tube35.67USD tube
Fluticasone Propionate 0.05% Cream 30 gm Tube35.67USD tube
Cutivate 0.005% Ointment 15 gm Tube32.99USD tube
Cutivate 0.05% Cream 15 gm Tube32.99USD tube
Advair hfa 230-21 mcg inhaler25.04USD g
Fluticasone Propionate 0.005% Ointment 15 gm Tube23.14USD tube
Fluticasone Propionate 0.05% Cream 15 gm Tube23.14USD tube
Advair hfa 115-21 mcg inhaler18.13USD g
Flovent hfa 220 mcg inhaler15.54USD g
Advair hfa 45-21 mcg inhaler14.59USD g
Flovent hfa 110 mcg inhaler12.26USD g
Flovent hfa 44 mcg inhaler10.99USD g
Flonase 0.05% nasal spray5.68USD g
Advair 500-50 diskus5.26USD each
Advair 250-50 diskus4.0USD each
Cutivate 0.05% cream3.48USD g
Advair 100-50 diskus3.22USD each
Flovent 250 mcg diskus2.45USD each
Flovent 100 mcg diskus1.83USD each
Flovent 50 mcg diskus1.74USD each
Flovent Diskus 500 mcg/dose Metered Inhalation Powder1.55USD dose
Flovent Diskus 250 mcg/dose Metered Inhalation Powder0.77USD dose
Flovent Hfa 250 mcg/dose Metered Dose Aerosol0.77USD dose
Flovent Hfa 125 mcg/dose Metered Dose Aerosol0.39USD dose
Flovent Hfa 50 mcg/dose Metered Dose Aerosol0.22USD dose
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada21256672000-03-132012-12-04
Canada23179992004-11-092020-09-11
United States75004442005-07-042025-07-04
United StatesRE400451993-09-072010-09-07
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point272-273 °CNot Available
water solubility0.51 mg/L (insoluble)Not Available
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0114 mg/mLALOGPS
logP3.69ALOGPS
logP3.72ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.65 m3·mol-1ChemAxon
Polarizability49.26 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Joseph Kaspi, Oded Arad, Michael Brand, Moty Shookrun, Simona Malka, Mohammed Alnabari, Shalom Hazan, Vlado Malesevic, “Synthesis and powder preparation of fluticasone propionate.” U.S. Patent US20060009435, issued January 12, 2006.

US20060009435
General ReferencesNot Available
External Links
ATC CodesD07AC17R01AD08R03BA05
AHFS Codes
  • 52:08.08
  • 68:04.00
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (159 KB)
MSDSDownload (39 KB)
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Fluticasone Propionate.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Fluticasone Propionate.
AmphetamineAmphetamine may decrease the sedative activities of Fluticasone Propionate.
AtazanavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Atazanavir.
BaclofenBaclofen may increase the central nervous system depressant (CNS depressant) activities of Fluticasone Propionate.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Fluticasone Propionate.
BoceprevirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Boceprevir.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Fluticasone Propionate.
CathinoneCathinone may decrease the sedative activities of Fluticasone Propionate.
CeritinibThe serum concentration of Fluticasone Propionate can be increased when it is combined with Ceritinib.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Fluticasone Propionate.
Cimetropium BromideFluticasone Propionate may increase the anticholinergic activities of Cimetropium Bromide.
CitalopramFluticasone Propionate may increase the QTc-prolonging activities of Citalopram.
ClarithromycinThe serum concentration of Fluticasone Propionate can be increased when it is combined with Clarithromycin.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Fluticasone Propionate.
CobicistatThe serum concentration of Fluticasone Propionate can be increased when it is combined with Cobicistat.
DarunavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Darunavir.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Fluticasone Propionate.
DofetilideFluticasone Propionate may increase the QTc-prolonging activities of Dofetilide.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Fluticasone Propionate.
DoxofyllineThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Fluticasone Propionate.
EluxadolineFluticasone Propionate may increase the activities of Eluxadoline.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Fluticasone Propionate.
EsmololEsmolol may decrease the activities of Fluticasone Propionate.
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Fluticasone Propionate.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Fluticasone Propionate.
FluconazoleThe metabolism of Fluticasone Propionate can be decreased when combined with Fluconazole.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Fluticasone Propionate.
Fusidic AcidThe serum concentration of Fluticasone Propionate can be increased when it is combined with Fusidic Acid.
GoserelinFluticasone Propionate may increase the QTc-prolonging activities of Goserelin.
IdelalisibThe serum concentration of Fluticasone Propionate can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Indinavir.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Fluticasone Propionate.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Fluticasone Propionate.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Fluticasone Propionate.
ItraconazoleThe serum concentration of Fluticasone Propionate can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Fluticasone Propionate can be increased when it is combined with Ketoconazole.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Fluticasone Propionate.
LeuprolideFluticasone Propionate may increase the QTc-prolonging activities of Leuprolide.
LopinavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Lopinavir.
LorazepamLorazepam may increase the central nervous system depressant (CNS depressant) activities of Fluticasone Propionate.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Fluticasone Propionate.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fluticasone Propionate.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Fluticasone Propionate.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fluticasone Propionate.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Fluticasone Propionate.
NadololNadolol may decrease the activities of Fluticasone Propionate.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Fluticasone Propionate.
NefazodoneThe serum concentration of Fluticasone Propionate can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Nelfinavir.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Fluticasone Propionate.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fluticasone Propionate.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fluticasone Propionate.
ParoxetineThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Paroxetine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Fluticasone Propionate.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Fluticasone Propionate.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Fluticasone Propionate.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Fluticasone Propionate.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fluticasone Propionate.
PosaconazoleThe serum concentration of Fluticasone Propionate can be increased when it is combined with Posaconazole.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Fluticasone Propionate.
RamosetronFluticasone Propionate may increase the activities of Ramosetron.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fluticasone Propionate.
RitonavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Ritonavir.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Fluticasone Propionate.
SaquinavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Saquinavir.
TacrineThe therapeutic efficacy of Fluticasone Propionate can be decreased when used in combination with Tacrine.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Fluticasone Propionate.
TelaprevirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Fluticasone Propionate can be increased when it is combined with Telithromycin.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Fluticasone Propionate.
TipranavirThe serum concentration of Fluticasone Propionate can be increased when it is combined with Tipranavir.
TorasemideFluticasone Propionate may increase the hypokalemic activities of Torasemide.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Fluticasone Propionate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Fluticasone Propionate.
VoriconazoleThe serum concentration of Fluticasone Propionate can be increased when it is combined with Voriconazole.
Food InteractionsNot Available

Targets

1. Glucocorticoid receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

References:

  1. Andersson O, Cassel TN, Gronneberg R, Bronnegard M, Stierna P, Nord M: In vivo modulation of glucocorticoid receptor mRNA by inhaled fluticasone propionate in bronchial mucosa and blood lymphocytes in subjects with mild asthma. J Allergy Clin Immunol. 1999 Apr;103(4):595-600. Pubmed
  2. Lumry WR: A review of the preclinical and clinical data of newer intranasal steroids used in the treatment of allergic rhinitis. J Allergy Clin Immunol. 1999 Oct;104(4 Pt 1):S150-8. Pubmed
  3. Zhang X, Moilanen E, Kankaanranta H: Beclomethasone, budesonide and fluticasone propionate inhibit human neutrophil apoptosis. Eur J Pharmacol. 2001 Nov 23;431(3):365-71. Pubmed
  4. Hogger P, Rohdewald P: Binding kinetics of fluticasone propionate to the human glucocorticoid receptor. Steroids. 1994 Oct;59(10):597-602. Pubmed
  5. Johnson M: Fluticasone propionate: safety profile. Cutis. 1996 Feb;57(2 Suppl):10-2. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Progesterone receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Progesterone receptor P06401 Details

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
  2. Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. Pubmed

3. Cytosolic phospholipase A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytosolic phospholipase A2 P47712 Details

References:

  1. Sano A, Munoz NM, Sano H, Choi J, Zhu X, Jacobs B, Leff AR: Inhibition of cPLA2 translocation and leukotriene C4 secretion by fluticasone propionate in exogenously activated human eosinophils. Am J Respir Crit Care Med. 1999 Jun;159(6):1903-9. Pubmed
  2. Myo S, Zhu X, Myou S, Meliton AY, Liu J, Boetticher E, Lambertino AT, Xu C, Munoz NM, Leff AR: Additive blockade of beta 2-integrin adhesion of eosinophils by salmeterol and fluticasone propionate. Eur Respir J. 2004 Apr;23(4):511-7. Pubmed

4. Mineralocorticoid receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Mineralocorticoid receptor P08235 Details

References:

  1. Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ: Mometasone furoate is a less specific glucocorticoid than fluticasone propionate. Eur Respir J. 2002 Dec;20(6):1386-92. Pubmed
  2. 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

Enzymes

1. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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
  2. Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. Pubmed

2. Cytochrome P450 3A5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

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
  2. Murai T, Reilly CA, Ward RM, Yost GS: The inhaled glucocorticoid fluticasone propionate efficiently inactivates cytochrome P450 3A5, a predominant lung P450 enzyme. Chem Res Toxicol. 2010 Aug 16;23(8):1356-64. Pubmed

3. Cytochrome P450 3A7

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

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

Carriers

1. Corticosteroid-binding globulin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

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
  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

Comments
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Drug created on June 13, 2005 07:24 / Updated on December 04, 2015 15:07