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
KEGG Drug
D09697
ChemSpider
24663012
ChEBI
75040
ChEMBL
CHEMBL1084172
Wikipedia
Vilanterol
Predicted Properties
PropertyValueSource
Water Solubility0.00118 mg/mLALOGPS
logP3.39ALOGPS
logP3.6Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)10.12Chemaxon
pKa (Strongest Basic)9.4Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area91.18 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity129.09 m3·mol-1Chemaxon
Polarizability53.69 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon