ChemicalBook > CAS DataBase List > Fluticasone propionate

Fluticasone propionate

Product Name
Fluticasone propionate
CAS No.
80474-14-2
Chemical Name
Fluticasone propionate
Synonyms
FLOVENT;Fluticasone propionate for impurity C identification CRS;CUTIVATE;Fluticasone propionate for impurity C identification;Zoflut;flutide;FLUNASE;FLONASE;cci18781;FLIXONASE
CBNumber
CB1252206
Molecular Formula
C25H31F3O5S
Formula Weight
500.57
MOL File
80474-14-2.mol
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Fluticasone propionate Property

Melting point:
275 °C
alpha 
D +30° (c = 0.35)
Boiling point:
568.3±50.0 °C(Predicted)
Density 
1.32±0.1 g/cm3(Predicted)
refractive index 
31 ° (C=1, Dioxane)
storage temp. 
Store at RT
solubility 
DMSO: ≥10 mg/mL
pka
12.53±0.70(Predicted)
form 
solid
color 
white
Merck 
14,4211
InChIKey
WMWTYOKRWGGJOA-CENSZEJFSA-N
CAS DataBase Reference
80474-14-2(CAS DataBase Reference)
EPA Substance Registry System
Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-,S-(fluoromethyl) ester, (6.alpha.,11.beta.,16.alpha.,17.alpha.)- (80474-14-2)
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Safety

Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
BV7980000
HS Code 
29372900
Toxicity
LD50 oral in rat: > 2gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F9428
Product name
Fluticasone propionate
Purity
≥98% (HPLC), powder
Packaging
5mg
Price
$114
Updated
2024/03/01
Sigma-Aldrich
Product number
1285873
Product name
Fluticasone propionate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$2140
Updated
2024/03/01
TCI Chemical
Product number
F0525
Product name
Fluticasone Propionate
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$198
Updated
2024/03/01
Cayman Chemical
Product number
20703
Product name
Fluticasone Propionate
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
20703
Product name
Fluticasone Propionate
Purity
≥98%
Packaging
5mg
Price
$70
Updated
2024/03/01
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Fluticasone propionate Chemical Properties,Usage,Production

Description

Fluticasone propionate is claimed to exert a topical effect on the lungs without significant systemic effects, due to its low systemic bioavailability.

Chemical Properties

Fluticasone propionate is a white to off-white powder with a molecular weight of 500.6, and 17 the empirical formula is C25H31F3O5S. It is practically insoluble in water, freely soluble in 18 dimethyl sulfoxide and dimethylformamide, and slightly soluble in methanol and 95% ethanol.

Originator

Glaxo (United Kingdom)

Uses

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(R). Fluticasone propionate is also available as a combination product of Azelastine Hydrochloride and Fluticasone Propionate called Dymista(TM). Dymista(TM) is indicated in patients over 12 years old for symptomatic relief of seasonal allergic rhinitis.

Uses

Fluticasone Propionate is a derivative of Flumethasone, a glucocorticoid that has antiallergic, anti-asthmatic, and anti-inflammatory properties. It is used in the treatment of seasonal rhinitis and asthma. Compared to beclomethasone dipropionate, fluticasone propionate is reported to have a comparable side effect profile, but twice the activity in the treatment of asthma.

Preparation

Fluticasone propionate, synthesized by Glaxo Wellcome and launched in 1993, is a trifluorinated glucocorticosteroid. It shows good topical antiinflammatory activity and is commonly used as a safe and effective inhaled treatment for asthma and allergic rhinitis.

Fluticasone propionate can be synthesized from 9 by using BrCH2F,2a ClCH2F,5a or S-(monofluoromethyl) diarylsulfonium tetrafluoroborate 5f,g directly. Using BrCH2F can get an ideal yield; however, BrCH2F is costly and will destroy to the ozone layer. In addition, 9 reacted with BrCH2Cl or Br2CH2 and then by an anion exchange with AgF,2c,5e KF, or tetrabutylammonium fluoride5b to afford 1 in a low yield.
Improved Synthesis of Fluticasone Propionate

Definition

ChEBI: Fluticasone propionate is a trifluorinated corticosteroid that consists of 6alpha,9-difluoro-11beta,17alpha-dihydroxy-17beta-{[(fluoromethyl)sulfanyl]carbonyl}-16-methyl-3-oxoandrosta-1,4-diene bearing a propionyl substituent at position 17; has anti-inflammatory, anti-asthmatic and anti-allergic activity. It has a role as an anti-allergic agent, an anti-asthmatic drug, an anti-inflammatory drug, a dermatologic drug, a bronchodilator agent and an adrenergic agent. It is a corticosteroid, a steroid ester, an 11beta-hydroxy steroid, a propanoate ester, a fluorinated steroid, a thioester and a 3-oxo-Delta(1),Delta(4)-steroid. It derives from a fluticasone. It derives from a hydride of an androstane.

Manufacturing Process

A solution of S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo17α-propionyloxyandrosta-1,4-diene-17β-carbothioate (310 mg) in acetonitrile (10 ml) was stirred with silver fluoride (947 mg) for 3 days at room temperature in the dark. Ethyl acetate (100 ml) was added and the mixture was filtered through kieselguhr. The filtrate was washed successively with 2 N hydrochloric acid, water, saturated brine, then dried. The solvent was removed and the residue was subjected to column chromatography in chloroform then chloroform-acetone (19:1). The product was eluted with ethyl acetate and crystallised on concentration of the solution to give S-fluoromethyl 6α,9αdifluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene17β-carbothioate (0.075 g); melting point 272-273°C (dec.), [α]D= +30° (c 0.35).

brand name

Cutivate (Altana); Flonase (GlaxoSmithKline); Flovent (GlaxoSmithKline);Flixonase.

Therapeutic Function

Glucocorticoid

General Description

Fluticasone Propionate is the propionate salt form of fluticasone, a synthetic trifluorinated glucocorticoid receptor agonist with antiallergic, antiinflammatory and antipruritic effects. Binding and activation of the glucocorticoid receptor results in the activation of lipocortin that in turn inhibits cytosolic phospholipase A2, which triggers cascade of reactions involved in synthesis of inflammatory mediators, such as prostaglandins and leukotrienes. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, thereby leads to dephosphorylation and inactivation of Jun N-terminal kinase directly inhibiting c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibits the transcription of cyclooxygenase 2, which is essential for prostaglandin production.

Biological Activity

Fluticasone propionate is a high affinity, selective glucocorticoid receptor agonist (Kd = 0.5 nM). Potently stimulates glucocorticoid receptor-mediated transactivation of gene expression and enhances human eosinophil apoptosis (EC50 = 3.7 nM) in vitro. Inhibits mast cell accumulation in nasal mucosa following topical administration. Lipophilic anti-inflammatory agent with low oral bioavailability. Also potentiates KV1 channels (EC50 = 37 nM).

Mechanism of action

Fluticasone propionate has a unique C-20 thioflouromethyl group, and that, in combination with the 17α-propionate ester, gives it 36-fold the glucocorticoid receptor affinity as compared to beclomethasone dipropionate and twofold the affinity as compared to budesonide. The 9α-flouro group increases both glucocorticoid and mineralocorticoid activities, and the 6α-flouro group enhances only the glucocorticoid action. Studies have determined that the effectiveness of inhaled fluticasone propionate results from a local rather than a systemic effect.

Side effects

In controlled US studies, more than 3,300 patients with seasonal allergic, perennial allergic, or perennial nonallergic rhinitis received treatment with intranasal fluticasone propionate. In general, adverse reactions in clinical studies have been primarily associated with irritation of the nasal mucous membranes, and the adverse reactions were reported with approximately the same frequency by patients treated with the vehicle itself. The complaints did not usually interfere with treatment. Less than 2% of patients in clinical trials discontinued because of adverse events; this rate was similar for vehicle placebo and active comparators.
Systemic corticosteroid side effects were not reported during controlled clinical studies up to 6 months’ duration with FLONASE Nasal Spray. If recommended doses are exceeded, however, or if individuals are particularly sensitive or taking FLONASE Nasal Spray in conjunction with administration of other corticosteroids, symptoms of hypercorticism, e.g., Cushing syndrome, could occur.
PRESCRIBING INFORMATION

Veterinary Drugs and Treatments

While there are topical forms of fluticasone, most veterinary interests are in the inhaled versions of the drug. The aerosol for pulmonary inhalation appears to be effective in treating feline asthma, recurrent airway obstruction (RAO, heaves) or inflammatory airway disease (IAD) in horses, and dogs with chronic tracheobronchial disease. While the majority of small animal use has been with fluticasone, there are several other aerosol corticosteroids for inhalation (beclomethasone dipropionate, flunisolide, and triamcinolone acetonide) that theoretically could be used for the same purpose. The nasal inhalation corticosteroid products may be useful for allergyrelated chronic rhinosinusitis in cats and dogs.

Metabolism

Interestingly, less than 1% of the swallowed dose is bioavailable, in contrast to the fact that the majority of the inhaled dose is systemically available and highly protein bound. Fluticasone propionate is not a prodrug and is extensively metabolized by the liver. The only detectable metabolite is the 17β-carboxylic acid derived from CYP3A4 oxidation. This metabolite has 2,000-fold less affinity for the glucocorticoid receptor than the parent drug. Elimination is through both the feces and the urine, with the relative amounts determined by the route of administration. Fluticasone propionate is available in aerosol and powder inhalation formulations.

storage

Room temperature

Dosage

Adults: The recommended starting dosage in adults is 2 sprays (50 mcg of fluticasone propionate each) in each nostril once daily (total daily dose, 200 mcg). The same dosage divided into 100 mcg given twice daily (e.g., 8 a.m. and 8 p.m.) is also effective. After the first few days, patients may be able to reduce their dosage to 100 mcg (1 spray in each nostril) once daily for maintenance therapy. Some patients (12 years of age and older) with seasonal allergic rhinitis may find as-needed use of 200 mcg once daily effective for symptom control (see Clinical Trials). Greater symptom control may be achieved with scheduled regular use.

Fluticasone propionate Preparation Products And Raw materials

Raw materials

3-METHOXYPROPIONIC ACID Bromofluoromethane Dimethyl sulfide

Preparation Products

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View Lastest Price from Fluticasone propionate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Fluticasone propionate 80474-14-2
Price
US $0.00/Kg/Bag
Min. Order
1g
Purity
98%-101%
Supply Ability
10 KGS
Release date
2021-06-19
Hangzhou Hyper Chemicals Limited
Product
Fluticasone propionate 80474-14-2
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%, EP
Supply Ability
5,000KG
Release date
2024-06-13
Hebei Yanxi Chemical Co., Ltd.
Product
Fluticasone propionate 80474-14-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100tons
Release date
2023-08-16

80474-14-2, Fluticasone propionateRelated Search:

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  • s-fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
  • -17-(1-oxopropoxy)-,s-(fluoromethyl)ester,(6-alpha,11-beta,16-alpha,17-alph
  • androsta-1,4-diene-17-carbothioicacid,6,9-difluoro-11-hydroxy-16-methyl-3-oxo
  • cci18781
  • fluticasone17-propionate
  • flutide
  • (6A,11B,16A,17A)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID FLUOROMETHYL ESTER
  • (6 ALPHA,11 BETA,16 ALPHA,17 ALPHA)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID FLUOROMETHYL ESTER
  • (6ALPHA, 11BETA, 16ALPHA, 17ALPHA)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID S-(FLUOROMETHYL) ESTER
  • Fluticasone Propionate - C25H31F3O5S
  • Fluticasonepropiponate
  • (6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester
  • CCI-187881
  • CUTIVATE
  • FLUTICASONE-D5 PROPIONATE
  • FLUTICASONE PROPIONATE
  • FLUNASE
  • FLONASE
  • FLIXONASE
  • FLIXOTIDE
  • FLOVENT
  • CCI-187881, Cutivate, Flixonase, Flixotide, Flonaase, Flovent, Flunase
  • Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(fluoromethyl) ester, (6.alpha.,11.beta.,16.alpha.,17.alpha.)-
  • [(6S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
  • Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(fluoromethyl) ester, (6α,11β,16α,17α)-
  • Atemur Mite
  • Cutivate cream
  • Flixonase Nasal Spray
  • Flixotide Disk
  • Flixotide Disks
  • Flixotide Inhaler
  • Flonase Aq
  • Flovent Diskus
  • Flutide N
  • Flutivate
  • Zoflut
  • FLUTICASOUE PROPIONATE
  • (6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid S-(fluoromethyl) ester
  • S-fluoromethyl 6a,9a-difluoro-l l P-hydroxy-16 a- methyl-l7a-propionyloxy-3-oxoandrosta-l,4-diene-17~-carbothioat
  • (6α，11β，16α，17α)-6，9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1，4-diene-17-carbothioic acid S-(fluommethyl)ester
  • (6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioicacidfluoromethylester
  • Fluticasone Propionate (100 mg)
  • Fluticasone propiona
  • luticasone-d5 propionate
  • Fluticasone propionate (Flonase, VeraMyst)
  • (6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-Methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-c
  • CARBOTHIOIC ACID FLUOROMETHYL ESTER
  • Fluticasone Furoate API
  • (6α,11β,16α,17α)-androsta-1,4-diene-17-carbothioic acid-6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-S-(fluoromethyl) ester
  • Fluticasone propionate S-Fluoromethyl-6alpha,9alpha-difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-propionyloxyandrosta-1,4-diene-17beta-carbothioate
  • Fluticasone propionate Solution, 100ppm
  • Fluticasone Propimonate
  • Fluticasone propiote
  • Fluticasone propionate for impurity G identification
  • Fluticasone propionate for impurity C identification
  • Fluticasone Propinate
  • 6α,9-Difluoro-17-[[(fluoromethyl)sulphanyl]carbonyl]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-dien-17α-yl propanoate
  • Fluticasone propionate - micronised pharma grade