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| | Vilanterol Trifenatate Basic information |
| Product Name: | Vilanterol Trifenatate | | Synonyms: | Vilanterol triphenylacetate;GW642444M; GW 642444M; GW-642444M;Benzeneacetic acid, α,α-diphenyl-, coMpd. with (α1R)-α1-[[[6-[2-[(2,6-dichlorophenyl)Methoxy]ethoxy]hexyl]aMino]Methyl]-4-hydroxy-1,3-benzenediMethanol (1:1);vilanterol trifenatate;GW 642444M;GW642444M;GW-642444M;Vilanterol Trifenatate (API) | | CAS: | 503070-58-4 | | MF: | C44H49Cl2NO7 | | MW: | 774.78 | | EINECS: | 638-763-2 | | Product Categories: | Intermediate;503070-58-4 | | Mol File: | 503070-58-4.mol |  |
| | 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. |
| | Vilanterol Trifenatate Preparation Products And Raw materials |
| Raw materials | 4H-1,3-Benzodioxin, 6-[(1R)-2-bromo-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-2,2-dimethyl--->(1R)-2-[[6-[2-[(2,6-Dichlorobenzyl)oxy]ethoxy]hexyl]aMino]-1-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)ethanol-->Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)--->2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)--->Vilanterol-->Triphenylacetic acid |
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