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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
SynonymLanguageCode
CutivateNot AvailableNot Available
FluticasonGermanINN
FluticasonaSpanishINN
FluticasoneFrenchINN
Fluticasone propionateNot AvailableNot Available
FluticasonumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluticasone Propionatelotion.5 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2009-10-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flonasespray, metered50 ugnasalGlaxo Smith Kline Llc1994-11-082016-02-28Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent DISKUSpowder, metered50 ugrespiratory (inhalation)Glaxo Smith Kline Llc2007-05-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent DISKUSpowder, metered250 ugrespiratory (inhalation)Glaxo Smith Kline Llc2008-10-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent DISKUSpowder, metered100 ugrespiratory (inhalation)Glaxo Smith Kline Llc2008-10-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered44 ugrespiratory (inhalation)Glaxo Smith Kline Llc2007-04-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered110 ugrespiratory (inhalation)Glaxo Smith Kline Llc2007-01-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered220 ugrespiratory (inhalation)Glaxo Smith Kline Llc2007-01-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivatelotion.5 mg/mLtopicalPharma Derm, A Division Of Nycomed Us Inc.2009-10-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivatecream.5 mg/gtopicalPharma Derm A Division Of Fougera Pharmaceuticals Inc.1990-12-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cutivatelotion.5 mg/mLtopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2009-10-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Floventhfa HFAaerosol, metered44 ugrespiratory (inhalation)REMEDYREPACK INC.2013-06-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flonasespray, metered50 ugnasalREMEDYREPACK INC.2013-06-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered110 ugrespiratory (inhalation)Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-01-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered110 ugrespiratory (inhalation)Physicians Total Care, Inc.2005-07-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered220 ugrespiratory (inhalation)Physicians Total Care, Inc.2006-07-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flovent HFAaerosol, metered44 ugrespiratory (inhalation)Physicians Total Care, Inc.2009-02-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluticasone Propionatespray, metered50 ugnasalRoxane Laboratories, Inc2006-02-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalGlobal Pharmaceuticals, Division of Impax Laboratories Inc.2004-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalG&W Laboratories, Inc.2006-06-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalGW Laboratories, Inc2006-05-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalRebel Distributors Corp2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalPerrigo New York Inc2007-07-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalPerrigo New York Inc2006-09-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatelotion.5 mg/mLtopicalPerrigo New York Inc2013-08-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalHi Tech Pharmacal Co., Inc.2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalUnit Dose Services2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-06-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalREMEDYREPACK INC.2013-06-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalREMEDYREPACK INC.2013-12-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalREMEDYREPACK INC.2013-06-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalPhysicians Total Care, Inc.2006-09-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionateointment.05 mg/gtopicalPhysicians Total Care, Inc.2005-10-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalPhysicians Total Care, Inc.2006-03-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalClinical Solutions Wholesale2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalGolden State Medical Supply, Inc.2011-06-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasonespray, metered50 ugnasalMorton Grove Pharmaceuticals, Inc.2012-01-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalApotex Corp.2007-09-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalApotex Corp.2009-12-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatecream.5 mg/gtopicalDIRECT RX2014-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalProficient Rx LP2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatelotion.5 mg/mLtopicalGlenmark Generics Inc., USA2011-10-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ugnasalPreferred Pharmaceuticals, Inc.2013-04-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fluticasone Propionatespray, metered50 ug/.1gnasalPreferred Pharmaceuticals, Inc2012-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flonase ALLERGY RELIEFspray, metered50 ugnasalGlaxo Smith Kline Consumer Healthcare Lp2014-12-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
EzicasIntas
FlixonaseGlaxoSmithKline
FlixotideGlaxoSmithKline
FloventGlaxoSmithKline
FLOVENTHFANot Available
FlunaseGlaxoSmithKline
NasofanTeva
PirinaseGlaxoSmithKline
SeretideGlaxoSmithKline
Brand mixtures
Brand NameIngredients
ADVAIRFluticasone Propionate + Salmeterol
ADVAIRDISKUSFluticasone Propionate + Salmeterol
DymistaAzelastine hydrochloride and Fluticasone propionate
FlixotideFluticasone and Salmeterol
FlixoventFluticasone and Salmeterol
Flosal DiskusFluticasone and Salmeterol
Salts
Name/CASStructureProperties
Fluticasone Propionate
ThumbNot applicableDBSALT001035
CategoriesNot Available
CAS number80474-14-2
WeightAverage: 500.571
Monoisotopic: 500.184429407
Chemical FormulaC25H31F3O5S
InChI KeyWMWTYOKRWGGJOA-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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateInhibitor0.8988
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
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
Aerosol, meteredrespiratory (inhalation)110 ug
Aerosol, meteredrespiratory (inhalation)220 ug
Aerosol, meteredrespiratory (inhalation)44 ug
Creamtopical.5 mg/g
Lotiontopical.5 mg/mL
Ointmenttopical.05 mg/g
Powder, meteredrespiratory (inhalation)100 ug
Powder, meteredrespiratory (inhalation)250 ug
Powder, meteredrespiratory (inhalation)50 ug
Spray, meterednasal50 ug
Spray, meterednasal50 ug/.1g
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 ReferenceNot 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
AclidiniumMay enhance the anticholinergic effect of Anticholinergic Agents.
AmphetamineMay diminish the sedative effect of Antihistamines.
Benzylpenicilloyl PolylysineAntihistamines may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
BetahistineAntihistamines may diminish the therapeutic effect of Betahistine.
CathinoneMay diminish the sedative effect of Antihistamines.
DofetilideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Dofetilide.
DronabinolMay enhance the CNS depressant effect of CNS Depressants.
HyaluronidaseAntihistamines may diminish the therapeutic effect of Hyaluronidase.
ItoprideAnticholinergic Agents may diminish the therapeutic effect of Itopride.
LomitapideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Lomitapide.
Magnesium SulfateMay enhance the CNS depressant effect of CNS Depressants.
MetoclopramideAnticholinergic Agents may diminish the therapeutic effect of Metoclopramide.
MetyrosineCNS Depressants may enhance the sedative effect of Metyrosine.
MirabegronAnticholinergic Agents may enhance the adverse/toxic effect of Mirabegron.
NabiloneMay enhance the CNS depressant effect of CNS Depressants.
OrphenadrineCNS Depressants may enhance the CNS depressant effect of Orphenadrine.
PimozideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Pimozide.
Potassium ChlorideAnticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
PramipexoleCNS Depressants may enhance the sedative effect of Pramipexole.
PramlintideMay enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
RitonavirMay increase the serum concentration of Fluticasone (Nasal).
RopiniroleCNS Depressants may enhance the sedative effect of ROPINIRole.
RotigotineCNS Depressants may enhance the sedative effect of Rotigotine.
RufinamideMay enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
SecretinAnticholinergic Agents may diminish the therapeutic effect of Secretin.
TelaprevirMay increase the serum concentration of Fluticasone (Nasal).
ThalidomideCNS Depressants may enhance the CNS depressant effect of Thalidomide.
TiotropiumAnticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
TipranavirMay increase the serum concentration of Fluticasone (Nasal).
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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11