Vilanterol

Identification

Name

Vilanterol

Accession Number

DB09082

Description

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.

Type

Small Molecule

Groups

Approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Vilanterol (DB09082)

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Weight

Average: 486.43
Monoisotopic: 485.1735786

Chemical Formula

C₂₄H₃₃Cl₂NO₅

Synonyms

• Vilantérol
• Vilanterol
• Vilanterolum

External IDs

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

Pharmacology

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Indication

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.

Associated Conditions

• Asthma
• Chronic Obstructive Pulmonary Disease (COPD)

Contraindications & Blackbox Warnings

Contraindications & Blackbox Warnings

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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

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.

Hover over products below to view reaction partners

• Vilanterol
  • M29 (GW630200)
  • M33 (GSK932009)

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

Adverse Effects

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Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Abametapir	The serum concentration of Vilanterol can be increased when it is combined with Abametapir.
Abatacept	The risk or severity of adverse effects can be increased when Abatacept is combined with Vilanterol.
Acebutolol	The therapeutic efficacy of Vilanterol can be decreased when used in combination with Acebutolol.
Aceclofenac	Aceclofenac may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Vilanterol which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Aclidinium	Aclidinium may decrease the excretion rate of Vilanterol which could result in a higher serum level.

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Food Interactions

No interactions found.

Products

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Product Ingredients

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

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Anoro	Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2016-09-08	Not applicable
Anoro	Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2016-09-08	Not applicable
Anoro	Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)	Powder, metered	Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2016-09-08	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
Anoro Ellipta	Vilanterol (25 mcg) + Umeclidinium (62.5 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2014-03-14	Not applicable
Breo Ellipta	Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2015-04-30	Not applicable
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 (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)	REMEDYREPACK INC.	2019-04-17	Not applicable

Categories

ATC Codes

R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoate

• R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

R03AK10 — Vilanterol and fluticasone furoate

• R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

R03AL03 — Vilanterol and umeclidinium bromide

• R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

Drug Categories

• Adrenergic Agonists
• Adrenergic beta-2 Receptor Agonists
• Adrenergic beta-Agonists
• Adrenergics, Inhalants
• Agents producing tachycardia
• Agents that produce hypertension
• Agents to Treat Airway Disease
• Alcohols
• Benzene Derivatives
• Benzyl Compounds
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Substrates
• Drugs for Obstructive Airway Diseases
• Drugs that are Mainly Renally Excreted
• Hydrocarbons, Chlorinated
• Hydrocarbons, Halogenated
• Immunosuppressive Agents
• Potential QTc-Prolonging Agents
• QTc Prolonging Agents

Chemical TaxonomyProvided by Classyfire

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 / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Aromatic alcohols

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Substituents

1,2-aminoalcohol / 1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzyl alcohol / Benzylether / Chlorobenzene / Dialkyl ether / Ether / Halobenzene / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organochloride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenol / Primary alcohol / Secondary alcohol / Secondary aliphatic amine / Secondary amine

show 19 more

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols, benzyl alcohols, secondary amino compound, ether, dichlorobenzene (CHEBI:75037)

Chemical Identifiers

UNII

028LZY775B

CAS number

503068-34-6

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

References

General References

1. 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]
2. 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

RxNav

1424884

ChEBI

75037

ChEMBL

CHEMBL1198857

ZINC

ZINC000003991624

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Vilanterol

FDA label

Download (12.2 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Chronic Obstructive Pulmonary Disease (COPD)	2
4	Completed	Treatment	Asthma	2
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Not Yet Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Not Yet Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Heart Failure	1
4	Recruiting	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Withdrawn	Treatment	Asthma	1
4	Withdrawn	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Completed	Other	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)	55 µg
Aerosol, powder	Respiratory (inhalation)	55 mcg
Powder	Respiratory (inhalation)	62.5 mcg
Powder	Oral; Respiratory (inhalation)	55 mcg
Powder	Respiratory (inhalation)
Powder	Respiratory (inhalation)	92 MCG
Aerosol, powder	Respiratory (inhalation)	62.5 mcg
Powder, metered	Respiratory (inhalation)	184 MICROGRAMMI
Powder, metered	Respiratory (inhalation)	92 MICROGRAMMI
Aerosol, powder	Respiratory (inhalation)	100 mcg
Powder, metered	Respiratory (inhalation)	100 mcg
Powder	Respiratory (inhalation)	184 µg
Aerosol, powder	Respiratory (inhalation)	200 mcg
Powder, metered	Respiratory (inhalation)	200 mcg
Powder	Respiratory (inhalation)	92 µg
Powder	Respiratory (inhalation)	184 mcg
Powder	Oral; Respiratory (inhalation)	100 cg
Powder	Respiratory (inhalation)	184 MICROGRAMMI
Powder	Respiratory (inhalation)	92 MICROGRAMMI
Powder	Respiratory (inhalation)	25 mcg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
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

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

Targets

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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

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Drug created on August 31, 2015 17:12 / Updated on February 21, 2021 18:52