397864-44-7 Usage
Description
Fluticasone furoate is a synthetic corticosteroid derivative, closely related to fluticasone propionate, and is used as a nasal spray for the treatment of seasonal and perennial allergic rhinitis in adults and children aged two years and older. It is a potent ligand for the glucocorticoid receptor, with high lipophilicity due to its S-fluoromethyl carbothioate group, which enhances binding and retention by nasal tissue and minimizes systemic exposure. Fluticasone furoate is chemically derived from a readily available corticosteroid and is marketed under the brand name Veramyst.
Uses
Used in Pharmaceutical Industry:
Fluticasone furoate is used as an anti-inflammatory agent for the treatment of seasonal allergic rhinitis. Its high receptor affinity and lipophilicity contribute to its effectiveness in reducing inflammation and alleviating symptoms associated with allergic rhinitis.
Used in Respiratory Treatment:
Fluticasone furoate is used as a corticosteroid in combination with vilanterol trifenate for the treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD). Its potent anti-inflammatory properties help in managing COPD symptoms and improving lung function.
Used in Allergy Treatment:
Fluticasone furoate is used as a nasal spray for the treatment of perennial allergic rhinitis, providing relief from nasal symptoms such as sneezing, itching, and congestion.
Used in Nasal Polyp Treatment:
Fluticasone furoate is used in reducing inflammation in patient-derived nasal polyp tissue, decreasing the levels of various inflammatory cytokines, such as IFN-γ, IL-2, IL-5, IL-17, and TNF-α.
Used in Allergic Inflammation Treatment:
Fluticasone furoate is used in reducing eosinophil infiltration in bronchoalveolar lavage fluid (BALF) in a rat model of allergic inflammation, demonstrating its potential in treating allergic conditions.
Synthesis
The synthesis of fluticasone on large scale was
disclosed in the patent literature. The starting 6α ,9α-
difluoro-11β-17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-
diene-17β-carboxylic acid 35 was converted to the
analogous carbothioic acid 36 in 95% yield via activation
with carbonyl diimidazole, followed by reaction with hydrogen
sulfide gas. Conversion of the carbothioic
acid to fluticasone was completed through a three-step sequence
in a one pot process in 99% overall yield. Carbothioic
acid 36 and DMAP were dissolved in MEK. Tripropylamine
(TPA) was then added to the mixture at -8 to -5°C.
Neat furoyl chloride was then added dropwise over 2-3 minutes
and the resulting mixture was then stirred at -5 to 0°C
for 15 minutes generating a mixture of desired ester 37 and
thioanhydride 38. A solution of N-methylpiperazine in water
was then added dropwise over 2-3 minutes at -5 to 0°C to the crude reaction mixture and stirred for 10 minutes, which
enabled the conversion of thioanhydride 38 to the ester 37. A
solution of bromofluoromethane in MEK was then added
rapidly at 0°C and the resulting solution was stirred at 20°C
for 5 hours. After a simple work-up, fluticasone furoate (V)
was obtained in 99% overall yield from 36 with 97% purity.
Check Digit Verification of cas no
The CAS Registry Mumber 397864-44-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,9,7,8,6 and 4 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 397864-44:
(8*3)+(7*9)+(6*7)+(5*8)+(4*6)+(3*4)+(2*4)+(1*4)=217
217 % 10 = 7
So 397864-44-7 is a valid CAS Registry Number.
397864-44-7Relevant articles and documents
X-ray crystal structure of the novel enhanced-affinity glucocorticoid agonist fluticasone furoate in the glucocorticoid receptor-ligand binding domain
Biggadike, Keith,Bledsoe, Randy K.,Hassell, Anne M.,Kirk, Barrie E.,McLay, Iain M.,Shewchuk, Lisa M.,Stewart, Eugene L.
, p. 3349 - 3352 (2008)
An X-ray crystal structure is reported for the novel enhanced-affinity glucocorticoid agonist fluticasone furoate (FF) in the ligand binding domain of the glucocorticoid receptor. Comparison of this structure with those of dexamethasone and fluticasone pr
Preparation method of fluticasone furoate
-
Paragraph 0059; 0060; 0061; 0062; 0063, (2017/04/29)
The invention relates to a preparation method of fluticasone furoate, especially preparation and purification of an intermediate 6alpha, 9alpha-difluoro-17alpha-[(2-furylcarbonyl)oxy]-11beta-hydroxy-16alpha-methyl-3-oxo-androstane-1,4-diene-17beta-thiocarboxylic acid. The preparation method comprises the following steps: in the presence of alkali and alcoholic solvent, a compound as shown in the formula VIII is converted into a mixture containing the compound of formula II; the mixture containing the compound of formula II is mixed with an aqueous solution of inorganic base and an ester solvent; a water phase is separated; pH value of the water phase is regulated by the use of acid until a solid is precipitated out; and the solid is separated. The invention provides a preparation method capable of remarkably raising purity of fluticasone furoate. Safety of drug application is guaranteed.
Method for the Production of Fluoromethyl Esters of Androstan-17 beta Carboxylic Acids
-
, (2014/07/23)
Described herein are processes for the preparation of monofluoromethylated organic biologically active compounds, starting from protected intermediates and/or reagents to obtain compounds such as fluticasone propionate and fluticasone furoate, in presence of decarboxylating reagents XeF2 and BrF3, or using FCH2SH as a reagent.
