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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H33Cl2NO5.C20H16O2
Molecular Weight 774.768
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILANTEROL TRIFENATATE

SMILES

OC(=O)C(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.OCC4=C(O)C=CC(=C4)[C@@H](O)CNCCCCCCOCCOCC5=C(Cl)C=CC=C5Cl

InChI

InChIKey=KLOLZALDXGTNQE-JIDHJSLPSA-N
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

HIDE SMILES / InChI
Molecular Formula C24H33Cl2NO5
Molecular Weight 486.429
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C20H16O2
Molecular Weight 288.3398
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2013
596
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 9.42 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/25816315/
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
UMECLIDINIUM
 [NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
239 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/25816315/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23284643/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/25816315/
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
UMECLIDINIUM
 [NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
214 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/25816315/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23284643/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/25816315/
25 μg 1 times / day multiple, oral
dose: 25 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: UMECLIDINIUM
UMECLIDINIUM
 [NO STEREO] VILANTEROL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.42 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23284643/
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
Other AEs: Nasopharyngitis, Constipation...
Other AEs:
Nasopharyngitis (1 patient)
Constipation (1 patient)
Hot flush (1 patient)
Muscle twitching (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23232038
500 ug multiple, oral
Highest studied dose
Dose: 500 ug
Route: oral
Route: multiple
Dose: 500 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/23043183
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:
https://pubmed.ncbi.nlm.nih.gov/23043183
Sources:
https://pubmed.ncbi.nlm.nih.gov/23043183
100 ug multiple, respiratory
Highest studied dose
Dose: 100 ug
Route: respiratory
Route: multiple
Dose: 100 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
Other AEs: Application site rash...
Other AEs:
Application site rash (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
Application site rash 1 patient
100 ug multiple, respiratory
Highest studied dose
Dose: 100 ug
Route: respiratory
Route: multiple
Dose: 100 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/23232038
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:
https://pubmed.ncbi.nlm.nih.gov/23232038
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
substrate
1037

inhibitor
1767
inhibitor
1852

substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

P-gp
1461
P-gp
1537

CYP2C8
693

CYP2C19
991

CYP1A2
1054
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 no [Inhibition 100 uM]
CYP1A2
1692
 no
CYP2C19
1553
 no
CYP2C9
1819
 no
CYP3A4
1925
 yes [IC50 4 uM]
CYP2D6
1891
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1054
 minor
CYP2C19
991
 minor
CYP2C8
693
 minor
CYP2C9
1037
 minor
CYP2D6
1217
 minor
P-gp
1537
 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
CYP3A4
1737
 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
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:75037
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75037
ChemicalBook
CB22542797
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22542797
MolPort
MolPort-044-560-195
https://www.molport.com/shop/molecule-link/MolPort-044-560-195
ZINC
ZINC000003991624
http://zinc15.docking.org/substances/ZINC000003991624
PubMed

PubMed

TitleDatePubMed
Synthesis and structure-activity relationships of long-acting beta2 adrenergic receptor agonists incorporating metabolic inactivation: an antedrug approach.
2010 Jun 10
Patents

Patents

07361787
3
07439393
7
07776895
3
07982067
3
08198483
3
20040122014
6
20040167167
4
JP2013536800A
2

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:46:59 UTC 2023
Edited
by admin
on Fri Dec 15 19:46:59 UTC 2023
Record UNII
40AHO2C6DG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VILANTEROL TRIFENATATE
DASH   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
VILANTEROL TRIFENATATE [JAN]
Common Name English
TRIPHENYLACETIC ACID-4-((1R)-2-((6-(2-(2,6-DICHOLOROBENZYL)OXY)ETHOXY)HEXYL)AMINO)-1-HYDROXYETHYL)-2-(HYDROXYMETHYL)PHENOL (1:1)
Common Name English
VILANTEROL TRIFENATATE COMPONENT ANORO ELLIPTA
Common Name English
GW642444M
Code English
VILANTEROL TRIFENATATE [MI]
Common Name English
ANORO ELLIPTA COMPONENT VILANTEROL TRIFENATATE
Brand Name English
BREO ELLIPTA COMPONENT VILANTEROL TRIFENATATE
Brand Name English
VILANTEROL TRIFENATATE [USAN]
Common Name English
VILANTEROL (AS TRIFENATATE)
Common Name English
GW-642444M
Code English
Vilanterol trifenatate [WHO-DD]
Common Name English
VILANTEROL TRIFENATATE [ORANGE BOOK]
Common Name English
VILANTEROL TRIFENATATE COMPONENT OF TRELEGY ELLIPTA
Brand Name English
TRELEGY ELLIPTA COMPONENT VILANTEROL TRIFENATATE
Brand Name English
TRIPHENYLACETIC ACID-4-((1R)-2-((6-(2-((2,6-DICHLOROBENZYL)OXY)ETHOXY)HEXYL)AMINO)-1-HYDROXYETHYL)-2-(HYDROXYMETHYL)PHENOL (1:1)
Common Name English
VILANTEROL TRIFENATATE COMPONENT OF BREO ELLIPTA
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
EMA ASSESSMENT REPORTS REVINITY ELLIPTA (AUTHORIZED: ASTHMA)
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
EMA ASSESSMENT REPORTS ANORO (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
Code System Code Type Description
MERCK INDEX
m11713
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
SMS_ID
100000128871
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL1198857
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
CAS
503070-58-4
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID80659232
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
DAILYMED
40AHO2C6DG
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
EVMPD
SUB36527
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
NCI_THESAURUS
C152876
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
USAN
UU-67
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
CHEBI
75040
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
DRUG BANK
DBSALT001121
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
FDA UNII
40AHO2C6DG
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
PUBCHEM
44482554
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY
JAPANESE REVIEW
ANORO ELLIPTA
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY APPROVED JULY 2014
RXCUI
1424883
Created by admin on Fri Dec 15 19:46:59 UTC 2023 , Edited by admin on Fri Dec 15 19:46:59 UTC 2023
PRIMARY RxNorm
Related Record Type Details
Structure of VINCRISTINE
SUBSTRATE -> TRANSPORTER
Structure of VILANTEROL
PARENT -> SALT/SOLVATE
Structure of VINORELBINE
SUBSTRATE -> TRANSPORTER
Related Record Type Details
Structure of VILANTEROL
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