Vilanterol

β2-AR agonist CAS# 503068-34-6

Vilanterol

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Chemical structure

Vilanterol

3D structure

Chemical Properties of Vilanterol

Cas No. 503068-34-6 SDF Download SDF
PubChem ID 10184665 Appearance Powder
Formula C24H33Cl2NO5 M.Wt 486.43
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (205.58 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 4-[(1R)-2-[6-[2-[(2,6-dichlorophenyl)methoxy]ethoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol
SMILES C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O)Cl
Standard InChIKey DAFYYTQWSAWIGS-DEOSSOPVSA-N
Standard InChI InChI=1S/C24H33Cl2NO5/c25-21-6-5-7-22(26)20(21)17-32-13-12-31-11-4-2-1-3-10-27-15-24(30)18-8-9-23(29)19(14-18)16-28/h5-9,14,24,27-30H,1-4,10-13,15-17H2/t24-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Vilanterol Dilution Calculator

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Vilanterol Molarity Calculator

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Preparing Stock Solutions of Vilanterol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0558 mL 10.279 mL 20.5579 mL 41.1159 mL 51.3949 mL
5 mM 0.4112 mL 2.0558 mL 4.1116 mL 8.2232 mL 10.279 mL
10 mM 0.2056 mL 1.0279 mL 2.0558 mL 4.1116 mL 5.1395 mL
50 mM 0.0411 mL 0.2056 mL 0.4112 mL 0.8223 mL 1.0279 mL
100 mM 0.0206 mL 0.1028 mL 0.2056 mL 0.4112 mL 0.5139 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Vilanterol

Vilanterol is a novel and selective agonist of β2-AR with a PEC50 value of 10.37±0.05 [1].

Vilanterol 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 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 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 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 has exhibited at least 1000-fold selectivity over both β1-and β3-AR subtypes [1].

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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References on Vilanterol

A randomised, phase III trial of once-daily fluticasone furoate/vilanterol 100/25 mug versus once-daily vilanterol 25 mug to evaluate the contribution on lung function of fluticasone furoate in the combination in patients with COPD.[Pubmed:28137501]

Respir Med. 2017 Feb;123:8-17.

BACKGROUND: The contribution of fluticasone furoate (FF) on lung function in the FF/Vilanterol (VI) 100/25 mug combination has been demonstrated numerically, but not statistically. METHODS: This multicentre, randomised, double-blind, controlled trial (GlaxoSmithKline study number 200820; clinicaltrials.gov NCT02105974) enrolled >/=40-year-old patients with chronic obstructive pulmonary disease (COPD), a >/=10-pack-year smoking history, a post-bronchodilator forced expiratory volume in 1 s (FEV1) 30-70% of the predicted value, a FEV1/forced vital capacity ratio of /=1 COPD exacerbation in the previous 12 months requiring corticosteroids, antibiotics and/or hospitalisation, and current COPD symptoms. Participants received FF/VI 100/25 mug or VI 25 mug once daily. The primary endpoint was the change from baseline in trough FEV1 at day 84. FINDINGS: 1620 patients were randomised and received at least one dose of FF/VI 100/25 mug (n = 806) or VI 25 mug (n = 814). At day 84, the FF/VI 100/25 mug group showed an adjusted mean treatment difference of 34 mL over VI 25 mug in change from baseline trough FEV1 (95% confidence interval [CI] 14-55; p = 0.001). There was no significant difference between the groups in the percentage of rescue medication-free 24-h periods. The FF/VI 100/25 mug group demonstrated a 42% risk reduction compared with the VI 25 mug group in time to first moderate/severe COPD exacerbation (95% CI 22-57; nominal p < 0.001). The incidence of on-treatment adverse events was similar between the groups. INTERPRETATION: The contribution of FF in the FF/VI 100/25 mug combination on lung function in COPD was statistically significant. FUNDING: GlaxoSmithKline.

Umeclidinium/vilanterol as step-up therapy from tiotropium in patients with moderate COPD: a randomized, parallel-group, 12-week study.[Pubmed:28280319]

Int J Chron Obstruct Pulmon Dis. 2017 Feb 24;12:745-755.

INTRODUCTION: Patients with COPD who remain symptomatic on long-acting bronchodilator monotherapy may benefit from step-up therapy to a long-acting bronchodilator combination. This study evaluated the efficacy and safety of umeclidinium (UMEC)/Vilanterol (VI) in patients with moderate COPD who remained symptomatic on tiotropium (TIO). METHODS: In this randomized, blinded, double-dummy, parallel-group study (NCT01899742), patients (N=494) who were prescribed TIO for >/=3 months at screening (forced expiratory volume in 1 s [FEV1]: 50%-70% of predicted; modified Medical Research Council [mMRC] score >/=1) and completed a 4-week run-in with TIO were randomized to UMEC/VI 62.5/25 microg or TIO 18 microg for 12 weeks. Efficacy assessments included trough FEV1 at Day 85 (primary end point), 0-3 h serial FEV1, rescue medication use, Transition Dyspnea Index (TDI), St George's Respiratory Questionnaire (SGRQ), and COPD Assessment Test (CAT). Safety evaluations included adverse events (AEs). RESULTS: Compared with TIO, UMEC/VI produced greater improvements in trough FEV1 (least squares [LS] mean difference: 88 mL at Day 85 [95% confidence interval {CI}: 45-131]; P<0.001) and FEV1 after 5 min on Day 1 (50 mL [95% CI: 27-72]; P<0.001). Reductions in rescue medication use over 12 weeks were greater with UMEC/VI versus TIO (LS mean change: -0.1 puffs/d [95% CI: -0.2-0.0]; P/=1 unit) with UMEC/VI (63%) versus TIO (49%; odds ratio at Day 84=1.78 [95% CI: 1.21-2.64]; P

A randomized trial of once-daily fluticasone furoate/vilanterol or vilanterol versus placebo to determine effects on arterial stiffness in COPD.[Pubmed:28176907]

Int J Chron Obstruct Pulmon Dis. 2017 Jan 19;12:351-365.

INTRODUCTION: Chronic obstructive pulmonary disease (COPD) is associated with increased cardiovascular morbidity and mortality. Elevated arterial stiffness, measured by aortic pulse wave velocity (aPWV), is a cardiovascular risk surrogate and is potentially modifiable by inhaled corticosteroid/long-acting beta2-agonist combinations in patients with COPD. MATERIALS AND METHODS: The effects of once-daily inhaled fluticasone furoate/Vilanterol (FF/VI) 100/25 microg, VI 25 microg, versus placebo on arterial stiffness in patients with COPD and baseline aPWV >/=11.0 m/s were investigated in a 24-week, multicenter, double-blind, randomized, stratified (by COPD exacerbation history), parallel-group, placebo-controlled trial. Eligible patients were >/=40 years old, with >/=10 pack-year smoking history, forced expiratory volume in 1 s (FEV1)/forced vital capacity

Description

Vilanterol (GW642444) is a long-acting β2-adrenoceptor (β2-AR) agonist with 24 h activity. The pEC50s for β2-AR,β1-AR and β3-AR is 10.37±0.05, 6.98±0.03 and 7.36±0.03, respectively.

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