Vilanterol Trifenatate Chemical Properties

Melting point:

131.9-134.2℃

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

Dichloromethane (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

Vilanterol Trifenatate Usage And Synthesis

Chemical Properties

Vilanterol trifenatate is a white powder with a molecular weight of 774.8, and the empirical formula is C24H33Cl2NO5.C20H16O2. It insoluble in water and slightly soluble in methanol, ethanol, acetonitrile and propan-2-ol. It is slightly hygroscopic. It is provided in a micronized form.

Uses

Vilanterol Trifenatate is a long-acting β2 adrenergic receptor Agonist with alonger than 24-hour activity in humans, and is being developed to be used in combination with FF. It is also highly selective for the β2-receptor, with over 1000-fold greater selectivity compared to β1-receptors. It demonstrates prolonged bronchodilation in subjects with asthma and COPD.

Preparation

Vilanterol trifenatate is synthesized by incorporation of an oxygen atom at the homobenzylic position of the right-hand side phenyl ring of (R)-salmeterol and has suitable chemical properties for inhaled administration. The combination in fluticasone furoate (FF) and vilanterol trifenatate (VI) in a single inhaler is the first once daily combination available on the market for the treatment of stable COPD.

Definition

ChEBI: Vilanterol Trifenatate is a triphenylacetate salt obtained by combining vilanterol with one equivalent of triphenylacetic acid. Used in combination with fluticasone furoate for treatment of bronchospasm associated with chronic obstructive pulmonary disease. It has a role as a beta-adrenergic agonist and a bronchodilator agent. It contains a vilanterol(1+).

Biological Activity

vilanterol trifenatate is a novel and selective agonist of β2-ar with a pec50 value of 10.37±0.05 [1].vilanterol trifenatate is a novel long-acting β2-ar agonist (laba) with 24h activity in development for inhaled once daily treatment. in the radioligand binding studies, vilanterol trifenatate has shown the binding affinity in the one-affinity site model with pkd values of 9.44±0.07 and 10.82±0.12 in the presence gpp(nh)p and absence gpp(nh)p, respectively. in dissociation studies, vilanterol trifenatate has been reported to bind from the β2-ar with a dissociation t1/2 value of 3.5 min in the presence of gpp(nh)p. vilanterol trifenatate has been found to have a good selectivity for β2-ar over the other β-ar receptor subtypes(β1and β3) with pec50 values of 10.37±0.05, 6.98±0.03 and 7.36±0.03, respectively. vilanterol trifenatate has exhibited at least 1000-fold selectivity over both β1-and β3-ar subtypes [1].

Dosage

The recommended and maximum dose is one inhalation of vilanterol trifenatate 25 micrograms once daily either morning or evening but at the same time every day.

Mode of action

Vilanterol Trifenatate is a selective long-acting beta2-receptor agonist (also referred to as a LABA). The pharmacologic effects of beta2-adrenoceptor agonist drugs, including vilanterol trifenatate, are at least in part attributable to stimulation of intracellular adenylate cyclase, the enzyme that catalyses the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

References

[1] slack rj1, barrett vj, morrison vs, sturton rg, emmons aj, ford aj, knowles rg.in vitro pharmacological characterization of vilanterol, a novel long-acting β2-adrenoceptor agonist with 24-hour duration of action.j pharmacol exp ther. 2013 jan; 344(1):218-30.

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