Vilanterol is a selective long-acting beta2-adrenergic agonist (LABA) with inherent 24-hour activity for once daily treatment of COPD and asthma. 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 approved for use in several combination products such as with fluticasone furoate under the tradename Breo Ellipta and in combination with umeclidinium bromide as Anoro Ellipta. Approved by the FDA in 2013, use of Breo Ellipta is indicated for the long-term, once-daily maintenance treatment of airflow obstruction in patients with COPD, including chronic bronchitis and emphysema. It is also indicated for once-daily maintenance treatment of asthma in patients aged 18 or older with reversible obstructive airways disease.

Structure

Similar Structures

Synonyms

Vilanterol
Vilantérol
Vilanterolum

External IDs

GW 642444M / GW 642444X / GW-642444 / GW-642444M / GW-642444X / GW642444 / GW642444M / GW642444X

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Vilanterol trifenatate	40AHO2C6DG	503070-58-4	KLOLZALDXGTNQE-JIDHJSLPSA-N

Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
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Anoro	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable
Anoro	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable
Anoro	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Anoro Ellipta	Vilanterol (25 mcg) + Umeclidinium (62.5 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2014-03-14	Not applicable
Anoro Ellipta	Vilanterol trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2014-01-31	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2013-08-26	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)	Powder	Respiratory (inhalation)	Glaxo Operations UK Ltd	2013-08-26	2018-01-08
Breo Ellipta	Vilanterol (25 mcg) + Fluticasone furoate (200 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2015-10-02	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)	Powder	Respiratory (inhalation)	Remedy Repack	2016-04-04	2016-04-05
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1)	Powder	Respiratory (inhalation)	A-S Medication Solutions	2015-04-30	Not applicable
Breo Ellipta	Vilanterol (25 mcg) + Fluticasone furoate (100 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2013-11-29	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)	Powder	Respiratory (inhalation)	REMEDYREPACK INC.	2019-04-17	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1)	Powder	Respiratory (inhalation)	Glaxo Operations UK Ltd	2015-04-30	2018-01-08

Categories

UNII

028LZY775B

CAS number

503068-34-6

Weight

Average: 486.43
Monoisotopic: 485.1735786

Chemical Formula

C₂₄H₃₃Cl₂NO₅

InChI Key

DAFYYTQWSAWIGS-DEOSSOPVSA-N

InChI

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

IUPAC Name

4-[(1R)-2-[(6-{2-[(2,6-dichlorophenyl)methoxy]ethoxy}hexyl)amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol

SMILES

OCC1=C(O)C=CC(=C1)[C@@H](O)CNCCCCCCOCCOCC1=C(Cl)C=CC=C1Cl

Pharmacology

Indication

Associated Conditions

Pharmacodynamics

Not Available

Mechanism of action

Vilanterol is a selective long-acting beta2-adrenergic agonist. 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.

Target	Actions	Organism
ABeta-2 adrenergic receptor	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Peak plasma concentrations are achieved within 10 minutes of inhalation. Absolute bioavailability was found to be 27.3% when administered by inhalation, whereas oral bioavailability was found to be less than 2% due to extensive first-pass metabolism. Systemic exposure is 24% higher in patients with COPD as compared to healthy subjects.

Volume of distribution

Following IV administration to healthy subjects, the mean volume of distribution at steady state was 661 L.

Protein binding

Binding to plasma protein was 93.9%.

Metabolism

Vilanterol is principally metabolized by cytochrome p450 3A4 (CYP3A4) to a range of metabolites with significantly reduced beta1- and beta2-agonist activity. The major route of metabolism was via O-dealkylation, with up to 78% of the recovered dose eliminated as O-dealkylated metabolites while N-Dealkylation and C-dealkylation were minor pathways, representing 5% of the recovered dose.

Route of elimination

Following oral administration, vilanterol is eliminated mainly by metabolism by CYP3A4 followed by excretion of metabolites in urine (70%) and feces (30%).

Half life

21.3 hr

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The metabolism of Vilanterol can be decreased when combined with (R)-warfarin.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Vilanterol.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Vilanterol.
1-benzylimidazole	The risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Vilanterol.
2-Methoxyethanol	The risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Vilanterol.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Vilanterol.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of hypertension can be increased when Vilanterol is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Vilanterol.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Vilanterol.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Vilanterol.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

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Action

Evidence Level

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

General References

Harrell AW, Siederer SK, Bal J, Patel NH, Young GC, Felgate CC, Pearce SJ, Roberts AD, Beaumont C, Emmons AJ, Pereira AI, Kempsford RD: Metabolism and disposition of vilanterol, a long-acting beta(2)-adrenoceptor agonist for inhalation use in humans. Drug Metab Dispos. 2013 Jan;41(1):89-100. doi: 10.1124/dmd.112.048603. Epub 2012 Oct 4. [PubMed:23043183]
Spyratos D, Sichletidis L: Umeclidinium bromide/vilanterol combination in the treatment of chronic obstructive pulmonary disease: a review. Ther Clin Risk Manag. 2015 Mar 25;11:481-7. doi: 10.2147/TCRM.S67491. eCollection 2015. [PubMed:25848294]

External Links

KEGG Drug: D09696
PubChem Compound: 10184665
PubChem Substance: 347827825
ChemSpider: 8360167
BindingDB: 50416060
ChEBI: 75037
ChEMBL: CHEMBL1198857
Wikipedia: Vilanterol

ATC Codes

R03AK10 — Vilanterol and fluticasone furoate

R03AL03 — Vilanterol and umeclidinium bromide

R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoate

FDA label

Download (12.2 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Asthma Bronchial	1
1	Completed	Not Available	Chronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers	1
1	Completed	Basic Science	Asthma Bronchial	1
1	Completed	Other	Asthma Bronchial	1
1	Completed	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
1	Completed	Prevention	Chronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers	1
1	Completed	Treatment	Asthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)	2
1	Completed	Treatment	Asthma Bronchial / Healthy Volunteers	2
1	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	4
1	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Healthy Volunteers	2
1, 2	Completed	Treatment	Asthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)	1
2	Active Not Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
2	Completed	Treatment	Asthma Bronchial	6
2	Completed	Treatment	Asthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)	2
2	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	7
2	Recruiting	Diagnostic	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Completed	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Completed	Treatment	Asthma Bronchial	5
3	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	18
4	Completed	Treatment	Asthma Bronchial	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Powder, metered	Respiratory (inhalation)
Powder	Respiratory (inhalation)

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US5873360	Yes	1999-02-23	2016-08-23
US7101866	No	2006-09-05	2021-08-03
US7439393	No	2008-10-21	2022-09-11
US6759398	No	2004-07-06	2021-08-03
USRE44874	No	2014-04-29	2023-03-23
US6537983	No	2003-03-25	2021-08-03
US8511304	No	2013-08-20	2027-06-14
US7629335	No	2009-12-08	2021-08-03
US8161968	No	2012-04-24	2028-02-05
US8746242	No	2014-06-10	2030-10-11
US8113199	No	2012-02-14	2027-10-23
US7776895	No	2010-08-17	2022-09-11
US8534281	No	2013-09-17	2029-08-10
US6878698	No	2005-04-12	2021-08-03
US8309572	No	2012-11-13	2025-04-27
US8183257	No	2012-05-22	2025-07-27
US7488827	No	2009-02-10	2025-04-27
US7498440	No	2009-03-03	2025-04-27
US9333310	No	2016-05-10	2027-10-02
US9750726	No	2017-09-05	2030-11-29
US9750762	No	2017-09-05	2030-11-29

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00118 mg/mL	ALOGPS
logP	3.39	ALOGPS
logP	3.6	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	91.18 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	129.09 m³·mol^-1	ChemAxon
Polarizability	53.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Benzylethers
Direct Parent: Benzylethers
Alternative Parents: Dichlorobenzenes / Benzyl alcohols / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Primary alcohols
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Substituents: Benzylether / Benzyl alcohol / 1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Chlorobenzene / Phenol / Halobenzene / Aryl chloride / Aryl halide
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Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: phenols, benzyl alcohols, secondary amino compound, ether, dichlorobenzene (CHEBI:75037)

Targets

Details1. Beta-2 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

Drug created on August 31, 2015 11:12 / Updated on May 01, 2019 13:06

Vilanterol

Identification

Structure for Vilanterol (DB09082)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

Enzymes