U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H33Cl2NO5
Molecular Weight 486.429
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILANTEROL

SMILES

OCC1=C(O)C=CC(=C1)[C@@H](O)CNCCCCCCOCCOCC2=C(Cl)C=CC=C2Cl

InChI

InChIKey=DAFYYTQWSAWIGS-DEOSSOPVSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.drugbank.ca/drugs/DB09082

Vilanterol (INN, USAN) is an ultra-long-acting β2 adrenoreceptor agonist (ultra-LABA), which was approved in May 2013 in combination with fluticasone furoate for sale as Breo Ellipta by GlaxoSmithKline for the treatment of chronic obstructive pulmonary disease (COPD). Its 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 relaxation of bronchial smooth muscle and inhibition of release of hypersensitivity mediators from mast cells in the lungs. Vilanterol is available in following combinations: a) with inhaled corticosteroid fluticasone furoate — fluticasone furoate/vilanterol (trade names Breo Ellipta , Relvar Ellipta; b) with muscarinic antagonist umeclidinium bromide — umeclidinium bromide/vilanterol (trade name Anoro Ellipta).

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.42 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
ANORO ELLIPTA

Approved Use

ANORO ELLIPTA is a combination of umeclidinium, an anticholinergic, and vilanterol, a long-acting beta2-adrenergic agonist (LABA), indicated for the long-term, once-daily, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD). Not indicated for relief of acute bronchospasm or for the treatment of asthma.

Launch Date

1.38732477E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
205 pg/mL
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
239 pg/mL
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
495.9 pg/mL
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
118 pg × h/mL
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
214 pg × h/mL
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
251.4 pg × h/mL
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.84 h
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.42 h
50 μg single, oral
dose: 50 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
[NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 100 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 100 ug, 1 times / day
Sources:
healthy, 29.1 years (range: 21-53 years)
n = 9
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
Population Size: 9
Sources:
Other AEs: Nasopharyngitis, Constipation...
Other AEs:
Nasopharyngitis (1 patient)
Constipation (1 patient)
Hot flush (1 patient)
Muscle twitching (1 patient)
Sources:
500 ug multiple, oral
Highest studied dose
Dose: 500 ug
Route: oral
Route: multiple
Dose: 500 ug
Sources:
healthy, 33.1 years (range: 19–47 years)
n = 9
Health Status: healthy
Age Group: 33.1 years (range: 19–47 years)
Sex: M
Population Size: 9
Sources:
100 ug multiple, respiratory
Highest studied dose
Dose: 100 ug
Route: respiratory
Route: multiple
Dose: 100 ug
Sources:
unhealthy, 36.9 years (range: 21-60 years)
n = 22
Health Status: unhealthy
Condition: asthma
Age Group: 36.9 years (range: 21-60 years)
Sex: M
Population Size: 22
Sources:
Other AEs: Application site rash...
Other AEs:
Application site rash (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Constipation 1 patient
100 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 100 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 100 ug, 1 times / day
Sources:
healthy, 29.1 years (range: 21-53 years)
n = 9
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
Population Size: 9
Sources:
Hot flush 1 patient
100 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 100 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 100 ug, 1 times / day
Sources:
healthy, 29.1 years (range: 21-53 years)
n = 9
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
Population Size: 9
Sources:
Muscle twitching 1 patient
100 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 100 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 100 ug, 1 times / day
Sources:
healthy, 29.1 years (range: 21-53 years)
n = 9
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
Population Size: 9
Sources:
Nasopharyngitis 1 patient
100 ug 1 times / day multiple, respiratory
Highest studied dose
Dose: 100 ug, 1 times / day
Route: respiratory
Route: multiple
Dose: 100 ug, 1 times / day
Sources:
healthy, 29.1 years (range: 21-53 years)
n = 9
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
Population Size: 9
Sources:
Application site rash 1 patient
100 ug multiple, respiratory
Highest studied dose
Dose: 100 ug
Route: respiratory
Route: multiple
Dose: 100 ug
Sources:
unhealthy, 36.9 years (range: 21-60 years)
n = 22
Health Status: unhealthy
Condition: asthma
Age Group: 36.9 years (range: 21-60 years)
Sex: M
Population Size: 22
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor
minor
minor
minor
minor
yes
unlikely
Comment: VI pharmacokinetics was not affected by P-gp inhibition. Drug interaction trials with a specific P-gp inhibitor and fluticasone furoate have not been conducted.
Page: 9.0
yes
yes (co-administration study)
Comment: Co-administration with strong CYP3A4 and potent P-gp inhibitor ketoconazole, resulted in modest increases in mean FF AUC(0-24) and Cmax (by 36% and 33%, respectively) and mean VI AUC(0-t) and Cmax (by 65% and 22%, respectively)
Page: 9.0

Sample Use Guides

ANORO ELLIPTA (umeclidinium/vilanterol 62.5 mcg/25 mcg) should be administered as 1 inhalation once daily by the orally inhaled route only. ANORO ELLIPTA should be used at the same time every day. Do not use ANORO ELLIPTA more than 1 time every 24 hours.
Route of Administration: Respiratory
Vilanterol (taken at 1nM) caused concentration related bronchodilation of human small airways when precontracted with histamine or carbachol and exhibited a comparable EC50 and efficacy (maximum percentage bronchodilation) within each spasmogen tested. EC50 value was 0.6 nM.
Name Type Language
VILANTEROL
INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
VILANTEROL [USAN]
Common Name English
1,3-BENZENEDIMETHANOL, .ALPHA.1-(((6-(2-((2,6-DICHLOROPHENYL)METHOXY)ETHOXY)HEXYL)AMINO)METHYL)-4-HYDROXY-, (.ALPHA.1R)-
Common Name English
VILANTEROL [VANDF]
Common Name English
GW642444
Code English
vilanterol [INN]
Common Name English
GW-642444
Code English
Vilanterol [WHO-DD]
Common Name English
GW642444X
Code English
GW-642444X
Code English
4-{(1R)-2-[(6-{2-[(2,6-Dichlorophenyl)methoxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol
Systematic Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS LAVENTAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
WHO-ATC R03AL08
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
NDF-RT N0000175779
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
WHO-VATC QR03AL03
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
WHO-ATC R03AL03
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
EMA ASSESSMENT REPORTS RELVAR ELLIPTA (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
WHO-ATC R03AK10
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
WHO-VATC QR03AK10
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
Code System Code Type Description
IUPHAR
7353
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
RXCUI
1424884
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY RxNorm
SMS_ID
100000138094
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
LACTMED
Vilanterol
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
CAS
503068-34-6
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
USAN
UU-68
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
DAILYMED
028LZY775B
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID80198318
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
DRUG BANK
DB09082
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1198857
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
INN
9198
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
PUBCHEM
10184665
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
MESH
C550468
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
NCI_THESAURUS
C152875
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
DRUG CENTRAL
4799
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
CHEBI
75037
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
WIKIPEDIA
Vilanterol
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
FDA UNII
028LZY775B
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY
EVMPD
SUB77409
Created by admin on Fri Dec 15 17:40:33 UTC 2023 , Edited by admin on Fri Dec 15 17:40:33 UTC 2023
PRIMARY