VILANTEROL

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

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

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Description

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

Primary Target	Pharmacology	Condition	Potency
adrenoceptor beta 2, surface 2	Agonist 2,752		9.42 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 175	Secondary		Approved 8,583	ANORO ELLIPTA

C_max

Value	Dose	Co-administered	Analyte	Population
495.9 pg/mL	50 μg single, oral		[NO STEREO] VILANTEROL plasma	Homo sapiens
239 pg/mL	25 μg 1 times / day multiple, oral		[NO STEREO] VILANTEROL plasma	Homo sapiens
205 pg/mL	25 μg 1 times / day multiple, oral	UMECLIDINIUM	[NO STEREO] VILANTEROL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
251.4 pg × h/mL	50 μg single, oral		[NO STEREO] VILANTEROL plasma	Homo sapiens
214 pg × h/mL	25 μg 1 times / day multiple, oral		[NO STEREO] VILANTEROL plasma	Homo sapiens
118 pg × h/mL	25 μg 1 times / day multiple, oral	UMECLIDINIUM	[NO STEREO] VILANTEROL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.42 h	50 μg single, oral		[NO STEREO] VILANTEROL plasma	Homo sapiens
1.84 h	25 μg 1 times / day multiple, oral	UMECLIDINIUM	[NO STEREO] VILANTEROL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
100 ug 1 times / day multiple, respiratory Highest studied dose	healthy, 29.1 years (range: 21-53 years)	Other AEs: Nasopharyngitis, Constipation...
500 ug multiple, oral Highest studied dose	healthy, 33.1 years (range: 19–47 years)
100 ug multiple, respiratory Highest studied dose	unhealthy, 36.9 years (range: 21-60 years)	Other AEs: Application site rash...

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AEs

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AE	Significance	Dose	Population
Constipation	1 patient	100 ug 1 times / day multiple, respiratory Highest studied dose	healthy, 29.1 years (range: 21-53 years)
Hot flush	1 patient	100 ug 1 times / day multiple, respiratory Highest studied dose	healthy, 29.1 years (range: 21-53 years)
Muscle twitching	1 patient	100 ug 1 times / day multiple, respiratory Highest studied dose	healthy, 29.1 years (range: 21-53 years)
Nasopharyngitis	1 patient	100 ug 1 times / day multiple, respiratory Highest studied dose	healthy, 29.1 years (range: 21-53 years)
Application site rash	1 patient	100 ug multiple, respiratory Highest studied dose	unhealthy, 36.9 years (range: 21-60 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	substrate 1,193 inhibitor 2,438	inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 P-gp 1,741	P-gp 2,052 CYP2C8 810 CYP2C19 1,119 CYP1A2 1,197

Drug as perpetrator

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Target	Modality	Activity
P-gp 1,932	inhibitor 4,027	no [Inhibition 100 uM]
CYP1A2 2,333	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no
CYP3A4 2,633	inhibitor 4,027	yes [IC50 4 uM]

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Drug as victim

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Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	minor
CYP2C19 1,119	substrate 4,014	minor
CYP2C8 810	substrate 4,014	minor
CYP2C9 1,193	substrate 4,014	minor
CYP2D6 1,388	substrate 4,014	minor

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Synthesis and structure-activity relationships of long-acting beta2 adrenergic receptor agonists incorporating metabolic inactivation: an antedrug approach.	2010 Jun 10	20462258

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Patents

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.

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Name

Type

Language

GW-642444

Preferred Name

English

VILANTEROL

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

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Classification Tree

Code System

Code

LUNG DISEASES, OBSTRUCTIVE

EMA ASSESSMENT REPORTS

LAVENTAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)

Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids

WHO-ATC

R03AL08

Established Pharmacologic Class

NDF-RT

N0000175779

Adrenergics in combination with anticholinergics

WHO-VATC

QR03AL03

Adrenergic Agonist

NCI_THESAURUS

C48149

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Code System

Code

Type

Description

IUPHAR

7353

PRIMARY

RXCUI

1424884

PRIMARY

RxNorm

SMS_ID

100000138094

PRIMARY

LACTMED

Vilanterol

PRIMARY

CAS

503068-34-6

PRIMARY

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ACTIVE MOIETY


					028LZY775B

VILANTEROL

METABOLITE (PARENT)


					BUJ94A3L43

5-((1R)-2-((6-(2-((2,6-DICHLOROPHENYL)METHOXY)ETHOXY)HEXYL)AMINO)-1-HYDROXYETHYL)-2-HYDROXYBENZOIC ACID

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator