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 774.7699
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILANTEROL TRIFENATATE

SMILES

C(CCCOCCOCc1c(cccc1Cl)Cl)CCNC[C@@]([H])(c2ccc(c(c2)CO)O)O.c1ccc(cc1)C(c2ccccc2)(c3ccccc3)C(=O)O

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 C20H16O2
Molecular Weight 288.3406
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H33Cl2NO5
Molecular Weight 486.4293
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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
9.41999999999999993 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

1387324800000
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)
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
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)
Health Status: healthy
Age Group: 33.1 years (range: 19–47 years)
Sex: M
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)
Health Status: unhealthy
Age Group: 36.9 years (range: 21-60 years)
Sex: M
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)
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
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)
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
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)
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
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)
Health Status: healthy
Age Group: 29.1 years (range: 21-53 years)
Sex: M
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)
Health Status: unhealthy
Age Group: 36.9 years (range: 21-60 years)
Sex: M
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
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
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

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:37:16 UTC 2021
Edited
by admin
on Sat Jun 26 09:37:16 UTC 2021
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
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 [WHO-DD]
Common Name English
VILANTEROL TRIFENATATE [USAN]
Common Name English
VILANTEROL (AS TRIFENATATE)
Common Name English
GW-642444M
Code 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 Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
EMA ASSESSMENT REPORTS REVINITY ELLIPTA (AUTHORIZED: ASTHMA)
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
NCI_THESAURUS C319
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
EMA ASSESSMENT REPORTS ANORO (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
Code System Code Type Description
MERCK INDEX
M11713
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL1198857
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
CAS
503070-58-4
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
EPA CompTox
503070-58-4
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
EVMPD
SUB36527
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
NCI_THESAURUS
C152876
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
DRUG BANK
DBSALT001121
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
FDA UNII
40AHO2C6DG
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
PUBCHEM
44482554
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY
JAPANESE REVIEW
ANORO ELLIPTA
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY APPROVED JULY 2014
RXCUI
1424883
Created by admin on Sat Jun 26 09:37:16 UTC 2021 , Edited by admin on Sat Jun 26 09:37:16 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SUBSTRATE -> TRANSPORTER
PARENT -> SALT/SOLVATE
SUBSTRATE -> TRANSPORTER
Related Record Type Details
ACTIVE MOIETY