Vilanterol

Identification

Summary

Vilanterol is a long-acting beta2-adrenergic agonist used in combination with other bronchodilators for the management of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema.

Brand Names
Anoro, Anoro Ellipta, Breo Ellipta, Trelegy Ellipta
Generic Name
Vilanterol
DrugBank Accession Number
DB09082
Background

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
Thumb
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

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
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.

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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
Medicalerrors
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Toxicity

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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AbametapirThe serum concentration of Vilanterol can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Vilanterol.
AcebutololThe therapeutic efficacy of Vilanterol can be decreased when used in combination with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Vilanterol which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Vilanterol which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Vilanterol trifenatate40AHO2C6DG503070-58-4KLOLZALDXGTNQE-JIDHJSLPSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
Anoro ElliptaVilanterol trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2014-01-31Not applicableUS flag
Anoro ElliptaVilanterol (25 mcg / act) + Umeclidinium (62.5 mcg / act)PowderRespiratory (inhalation)Glaxosmithkline Inc2014-03-14Not applicableCanada flag
ANORO ELLIPTAVilanterol trifenatate (40 MCG) + Umeclidinium bromide (74.2 MCG)PowderRespiratory (inhalation)บริษัท แกล็กโซสมิทไคล์น (ประเทศไทย) จำกัด2017-08-11Not applicableThailand flag
ANORO ELLIPTA 62.5/25 MCG KULLANIMA HAZIR INHALASYON TOZU ,3 X 30 DOZVilanterol trifenatate (22 mcg) + Umeclidinium bromide (55 mcg)Aerosol, powderRespiratory (inhalation)GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ANORO ELLIPTA 62.5/25 MCG KULLANIMA HAZIR INHALASYON TOZU ,30 DOZVilanterol trifenatate (22 mcg) + Umeclidinium bromide (55 mcg)Aerosol, powderRespiratory (inhalation)GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Breo ElliptaVilanterol (25 mcg / act) + Fluticasone furoate (200 mcg / act)PowderRespiratory (inhalation)Glaxosmithkline Inc2015-10-02Not applicableCanada flag
Breo ElliptaVilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2013-08-26Not applicableUS flag

Categories

ATC Codes
R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoateR03AK10 — Vilanterol and fluticasone furoateR03AL03 — Vilanterol and umeclidinium bromide
Drug Categories
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
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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
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, benzyl alcohols, secondary amino compound, ether, dichlorobenzene (CHEBI:75037)
Affected organisms
Not Available

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. [Article]
  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. [Article]
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
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2
4CompletedTreatmentAsthma2
4CompletedTreatmentAsthma in Children1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD) / Heart Failure1
4RecruitingOtherChronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4WithdrawnTreatmentAsthma1
4WithdrawnTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Aerosol, powderRespiratory (inhalation)
PowderOral; Respiratory (inhalation)55 mcg
PowderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
PowderOral; Respiratory (inhalation)
PowderRespiratory (inhalation)25 mcg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5873360Yes1999-02-232016-08-23US flag
US7101866No2006-09-052021-08-03US flag
US7439393No2008-10-212022-09-11US flag
US6759398No2004-07-062021-08-03US flag
USRE44874No2014-04-292023-03-23US flag
US6537983No2003-03-252021-08-03US flag
US8511304No2013-08-202027-06-14US flag
US7629335No2009-12-082021-08-03US flag
US8161968No2012-04-242028-02-05US flag
US8746242No2014-06-102030-10-11US flag
US8113199No2012-02-142027-10-23US flag
US7776895No2010-08-172022-09-11US flag
US8534281No2013-09-172029-08-10US flag
US6878698No2005-04-122021-08-03US flag
US8309572No2012-11-132025-04-27US flag
US8183257No2012-05-222025-07-27US flag
US7488827No2009-02-102025-04-27US flag
US7498440No2009-03-032025-04-27US flag
US9333310No2016-05-102027-10-02US flag
US9750726No2017-09-052030-11-29US flag
US9750762No2017-09-052030-11-29US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00118 mg/mLALOGPS
logP3.39ALOGPS
logP3.6ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)10.12ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area91.18 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity129.09 m3·mol-1ChemAxon
Polarizability53.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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

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 17:12 / Updated on May 07, 2021 21:34