Vilanterol trifenatateProduct ingredient for Vilanterol
- Name
- Vilanterol trifenatate
- Drug Entry
- Vilanterol
Vilanterol is a selective long-acting β2-adrenergic agonist (LABA) with inherent 24-hour activity for the once-daily treatment of COPD and asthma.1 This is in response to the need for longer-acting β2-adrenergic agonists to overcome poor patient compliance (due to the frequency of dosing regimens or complexities of drug administration).3 Vilanterol was designed based on the salmeterol molecular scaffold, particularly as a antedrug analog of salmeterol modification by modifying the salmeterol molecule to create homochiral compounds with the (R)-configuration.3 Vilanterol is 1000 and 400 fold more selective for β2 than β1 and β3 adrenoceptors, respectively, with a faster onset of action than salmeterol.4 Additionally, vilanterol demonstrated a significantly longer duration of action than salmeterol, with the bronchodilator effect still apparent at 22h.4 Vilanterol's pharmacological effect is attributable to stimulation of intracellular adenylyl cyclase which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cAMP). Increases in cyclic AMP are associated with the relaxation of bronchial smooth muscle and inhibition of the release of hypersensitivity mediators from mast cells in the lungs.2,3
Vilanterol is approved for use in several combination products such as with fluticasone furoate under the tradename BREO ELLIPTA, with [umeclidinium bromide] as ANORO ELLIPTA, and with both fluticasone furoate and [umeclidinium bromide] under the trade name TRELEGY ELLIPTA.8,7,6 BREO ELLIPTA is the first vilanterol-containing product to be approved by the FDA in May 2013, followed by ANORO ELLIPTA in December 2013 and TRELEGY ELLIPTA in September 2020.10,11,12 Although all 3 products are approved for the maintenance treatment of chronic obstructive pulmonary disease (COPD), only TRELEGY ELLIPTA and BREO ELLIPTA are approved for maintenance treatments of asthma in patients aged 18 years and older and 5 years and older respectively.8,7,6
- Accession Number
- DBSALT001121
- Structure
- Synonyms
- Not Available
- UNII
- 40AHO2C6DG
- CAS Number
- 503070-58-4
- Weight
- Average: 774.78
Monoisotopic: 773.2886083 - Chemical Formula
- C44H49Cl2NO7
- InChI Key
- KLOLZALDXGTNQE-JIDHJSLPSA-N
- InChI
- InChI=1S/C24H33Cl2NO5.C20H16O2/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;21-19(22)20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h5-9,14,24,27-30H,1-4,10-13,15-17H2;1-15H,(H,21,22)/t24-;/m0./s1
- IUPAC Name
- 4-[(1R)-2-[(6-{2-[(2,6-dichlorophenyl)methoxy]ethoxy}hexyl)amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol; triphenylacetic acid
- SMILES
- OC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OCC1=C(O)C=CC(=C1)[C@@H](O)CNCCCCCCOCCOCC1=C(Cl)C=CC=C1Cl
- External Links
- KEGG Drug
- D09697
- ChemSpider
- 24663012
- ChEBI
- 75040
- ChEMBL
- CHEMBL1084172
- Wikipedia
- Vilanterol
- Predicted Properties
Property Value Source Water Solubility 0.00118 mg/mL ALOGPS logP 3.39 ALOGPS logP 3.6 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 10.12 Chemaxon pKa (Strongest Basic) 9.4 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 91.18 Å2 Chemaxon Rotatable Bond Count 20 Chemaxon Refractivity 129.09 m3·mol-1 Chemaxon Polarizability 53.69 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon