Identification
- Name
- Vilanterol
- Accession Number
- DB09082 (DB06577)
- Type
- Small Molecule
- Groups
- Approved
- 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.
- Structure
Structure for Vilanterol (DB09082)
- Synonyms
- Vilantérol
- Vilanterol
- 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 Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAnoro Powder, metered Respiratory (inhalation) Glaxo Smith Kline (Ireland) Limited 2014-05-08 Not applicable EU 
Anoro Powder, metered Respiratory (inhalation) Glaxo Smith Kline (Ireland) Limited 2014-05-08 Not applicable EU Anoro Powder, metered Respiratory (inhalation) Glaxo Smith Kline (Ireland) Limited 2014-05-08 Not applicable EU Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- 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 Canada 
Anoro Ellipta Vilanterol trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2014-01-31 Not applicable US 
Breo Ellipta Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1) Powder Respiratory (inhalation) A-S Medication Solutions 2015-04-30 Not applicable US Breo Ellipta Vilanterol (25 mcg) + Fluticasone furoate (200 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 2015-10-02 Not applicable Canada Breo Ellipta Vilanterol (25 mcg) + Fluticasone furoate (100 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 2013-11-29 Not applicable Canada Breo Ellipta Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2015-04-30 Not applicable US Breo Ellipta Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1) Powder Respiratory (inhalation) GlaxoSmithKline LLC 2013-08-26 Not applicable US 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 US 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 US Breo Ellipta Vilanterol trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1) Powder Respiratory (inhalation) REMEDYREPACK INC. 2019-04-17 Not applicable US - 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
- 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
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
- 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 agonistHumans - 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
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured 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.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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.
Drug Interaction Unlock Additional Data1-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. 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-Methoxyamphetamine The risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Vilanterol. 5-methoxy-N,N-dimethyltryptamine The risk or severity of hypertension can be increased when Vilanterol is combined with 5-methoxy-N,N-dimethyltryptamine. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Vilanterol. 9-(N-methyl-L-isoleucine)-cyclosporin A The risk or severity of adverse effects can be increased when Vilanterol is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A. Abacavir Abacavir may decrease the excretion rate of Vilanterol which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
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
- RxNav
- 1424884
- ChEBI
- 75037
- ChEMBL
- CHEMBL1198857
- ZINC
- ZINC000003991624
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vilanterol
- 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
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- FDA label
- Download (12.2 MB)
Clinical Trials
- Clinical Trials
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 DataUS5873360 Yes 1999-02-23 2016-08-23 US US7101866 No 2006-09-05 2021-08-03 US US7439393 No 2008-10-21 2022-09-11 US US6759398 No 2004-07-06 2021-08-03 US USRE44874 No 2014-04-29 2023-03-23 US US6537983 No 2003-03-25 2021-08-03 US US8511304 No 2013-08-20 2027-06-14 US US7629335 No 2009-12-08 2021-08-03 US US8161968 No 2012-04-24 2028-02-05 US US8746242 No 2014-06-10 2030-10-11 US US8113199 No 2012-02-14 2027-10-23 US US7776895 No 2010-08-17 2022-09-11 US US8534281 No 2013-09-17 2029-08-10 US US6878698 No 2005-04-12 2021-08-03 US US8309572 No 2012-11-13 2025-04-27 US US8183257 No 2012-05-22 2025-07-27 US US7488827 No 2009-02-10 2025-04-27 US US7498440 No 2009-03-03 2025-04-27 US US9333310 No 2016-05-10 2027-10-02 US US9750726 No 2017-09-05 2030-11-29 US US9750762 No 2017-09-05 2030-11-29 US Additional Data Available- Filed On
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 show 4 more
- Substituents
- Benzylether / Benzyl alcohol / 1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Chlorobenzene / Phenol / Halobenzene / Aryl chloride / Aryl halide show 19 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, benzyl alcohols, secondary amino compound, ether, dichlorobenzene (CHEBI:75037)
Targets
- 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 11:12 / Updated on June 12, 2020 11:42
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