Vilanterol - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (1)

Targets (1)Enzymes (1)Biointeractions (2)

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

MOL SDF PDB SMILES InChI

Synonyms

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

vilantérol

External IDs

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

Product Ingredients

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

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Anoro	Umeclidinium Vilanterol	Powder, metered	Respiratory (inhalation)	Glaxo Group Limited	2014-05-08	Not applicable	EU
Anoro Ellipta	Umeclidinium Vilanterol	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2014-03-14	Not applicable	Canada
Breo Ellipta	Fluticasone furoate Vilanterol	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2013-11-29	Not applicable	Canada

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

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

Pharmacology

Indication

Structured Indications

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Beta-2 adrenergic receptor	Protein	yes	agonist	Human	P07550	details

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.

Substrate	Enzymes	Product
Vilanterol	Not Available	M29 (GW630200)	Details
Vilanterol	Not Available	M33 (GSK932009)	Details

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	Drug group
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.	Experimental
Acebutolol	Acebutolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Alprenolol	Alprenolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Withdrawn
Amineptine	The risk or severity of adverse effects can be increased when Amineptine is combined with Vilanterol.	Illicit, Withdrawn
Amiodarone	The metabolism of Vilanterol can be decreased when combined with Amiodarone.	Approved, Investigational
Amitriptyline	The risk or severity of adverse effects can be increased when Amitriptyline is combined with Vilanterol.	Approved
Anagrelide	Vilanterol may increase the QTc-prolonging activities of Anagrelide.	Approved
Aprepitant	The serum concentration of Vilanterol can be increased when it is combined with Aprepitant.	Approved, Investigational
Arsenic trioxide	Vilanterol may increase the QTc-prolonging activities of Arsenic trioxide.	Approved, Investigational
Artemether	Vilanterol may increase the QTc-prolonging activities of Artemether.	Approved
Asenapine	Vilanterol may increase the QTc-prolonging activities of Asenapine.	Approved
Atazanavir	The metabolism of Vilanterol can be decreased when combined with Atazanavir.	Approved, Investigational
Atenolol	Atenolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Atomoxetine	Atomoxetine may increase the tachycardic activities of Vilanterol.	Approved
Azithromycin	Vilanterol may increase the QTc-prolonging activities of Azithromycin.	Approved
BCG vaccine	The therapeutic efficacy of Bcg can be decreased when used in combination with Vilanterol.	Investigational
Bedaquiline	Vilanterol may increase the QTc-prolonging activities of Bedaquiline.	Approved
Bendroflumethiazide	Vilanterol may increase the hypokalemic activities of Bendroflumethiazide.	Approved
Benmoxin	The risk or severity of adverse effects can be increased when Benmoxin is combined with Vilanterol.	Withdrawn
Betahistine	The therapeutic efficacy of Vilanterol can be decreased when used in combination with Betahistine.	Approved
Betaxolol	Betaxolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Bexarotene	The serum concentration of Vilanterol can be decreased when it is combined with Bexarotene.	Approved, Investigational
Bisoprolol	Bisoprolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Boceprevir	The metabolism of Vilanterol can be decreased when combined with Boceprevir.	Withdrawn
Bopindolol	Bopindolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Bortezomib	The metabolism of Vilanterol can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Vilanterol can be decreased when it is combined with Bosentan.	Approved, Investigational
Bumetanide	Vilanterol may increase the hypokalemic activities of Bumetanide.	Approved
Bupranolol	Bupranolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Carbamazepine	The metabolism of Vilanterol can be increased when combined with Carbamazepine.	Approved, Investigational
Caroxazone	The risk or severity of adverse effects can be increased when Caroxazone is combined with Vilanterol.	Withdrawn
Carteolol	Carteolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Celiprolol	Celiprolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Investigational
Ceritinib	The serum concentration of Vilanterol can be increased when it is combined with Ceritinib.	Approved
Chloroquine	Vilanterol may increase the QTc-prolonging activities of Chloroquine.	Approved, Vet Approved
Chlorothiazide	Vilanterol may increase the hypokalemic activities of Chlorothiazide.	Approved, Vet Approved
Chlorpromazine	Vilanterol may increase the QTc-prolonging activities of Chlorpromazine.	Approved, Vet Approved
Chlorthalidone	Vilanterol may increase the hypokalemic activities of Chlorthalidone.	Approved
Ciprofloxacin	Vilanterol may increase the QTc-prolonging activities of Ciprofloxacin.	Approved, Investigational
Cisapride	Vilanterol may increase the QTc-prolonging activities of Cisapride.	Approved, Investigational, Withdrawn
Citalopram	Vilanterol may increase the QTc-prolonging activities of Citalopram.	Approved
Clarithromycin	The metabolism of Vilanterol can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Vilanterol can be decreased when combined with Clemastine.	Approved
Clomipramine	The risk or severity of adverse effects can be increased when Clomipramine is combined with Vilanterol.	Approved, Vet Approved
Clotrimazole	The metabolism of Vilanterol can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Clozapine	Vilanterol may increase the QTc-prolonging activities of Clozapine.	Approved
Cobicistat	The metabolism of Vilanterol can be decreased when combined with Cobicistat.	Approved
Conivaptan	The serum concentration of Vilanterol can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	Vilanterol may increase the QTc-prolonging activities of Crizotinib.	Approved
Cyclobenzaprine	The risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Vilanterol.	Approved
Cyclosporine	The metabolism of Vilanterol can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabrafenib	The serum concentration of Vilanterol can be decreased when it is combined with Dabrafenib.	Approved
Darunavir	The metabolism of Vilanterol can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Vilanterol can be increased when it is combined with Dasatinib.	Approved, Investigational
Deferasirox	The serum concentration of Vilanterol can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Vilanterol can be decreased when combined with Delavirdine.	Approved
Denosumab	The risk or severity of adverse effects can be increased when Denosumab is combined with Vilanterol.	Approved
Desipramine	The risk or severity of adverse effects can be increased when Desipramine is combined with Vilanterol.	Approved
Dexamethasone	The serum concentration of Vilanterol can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dihydroergotamine	The metabolism of Vilanterol can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	The metabolism of Vilanterol can be decreased when combined with Diltiazem.	Approved
Disopyramide	Vilanterol may increase the QTc-prolonging activities of Disopyramide.	Approved
Dofetilide	Vilanterol may increase the QTc-prolonging activities of Dofetilide.	Approved
Dolasetron	Vilanterol may increase the QTc-prolonging activities of Dolasetron.	Approved
Domperidone	Vilanterol may increase the QTc-prolonging activities of Domperidone.	Approved, Investigational, Vet Approved
Dosulepin	The risk or severity of adverse effects can be increased when Dosulepin is combined with Vilanterol.	Approved
Doxepin	The risk or severity of adverse effects can be increased when Doxepin is combined with Vilanterol.	Approved
Doxycycline	The metabolism of Vilanterol can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	Vilanterol may increase the QTc-prolonging activities of Dronedarone.	Approved
Droperidol	Vilanterol may increase the QTc-prolonging activities of Droperidol.	Approved, Vet Approved
Efavirenz	The serum concentration of Vilanterol can be decreased when it is combined with Efavirenz.	Approved, Investigational
Eliglustat	Vilanterol may increase the QTc-prolonging activities of Eliglustat.	Approved
Enzalutamide	The serum concentration of Vilanterol can be decreased when it is combined with Enzalutamide.	Approved
Erythromycin	Vilanterol may increase the QTc-prolonging activities of Erythromycin.	Approved, Vet Approved
Escitalopram	Vilanterol may increase the QTc-prolonging activities of Escitalopram.	Approved, Investigational
Eslicarbazepine acetate	The serum concentration of Vilanterol can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Esmirtazapine	The risk or severity of adverse effects can be increased when Esmirtazapine is combined with Vilanterol.	Investigational
Esmolol	Esmolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Etacrynic acid	Vilanterol may increase the hypokalemic activities of Etacrynic acid.	Approved
Etravirine	The serum concentration of Vilanterol can be decreased when it is combined with Etravirine.	Approved
Fingolimod	Vilanterol may increase the immunosuppressive activities of Fingolimod.	Approved, Investigational
Flecainide	Vilanterol may increase the QTc-prolonging activities of Flecainide.	Approved, Withdrawn
Fluconazole	The metabolism of Vilanterol can be decreased when combined with Fluconazole.	Approved
Fluoxetine	Vilanterol may increase the QTc-prolonging activities of Fluoxetine.	Approved, Vet Approved
Flupentixol	Vilanterol may increase the QTc-prolonging activities of Flupentixol.	Approved, Withdrawn
Fluvoxamine	The metabolism of Vilanterol can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Vilanterol can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Vilanterol can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Vilanterol can be increased when combined with Fosphenytoin.	Approved
Furazolidone	The risk or severity of adverse effects can be increased when Furazolidone is combined with Vilanterol.	Approved, Vet Approved
Furosemide	Vilanterol may increase the hypokalemic activities of Furosemide.	Approved, Vet Approved
Fusidic Acid	The serum concentration of Vilanterol can be increased when it is combined with Fusidic Acid.	Approved
G17DT	The risk or severity of adverse effects can be increased when Vilanterol is combined with G17DT.	Investigational
Gadobenic acid	Vilanterol may increase the QTc-prolonging activities of Gadobenic acid.	Approved
Gemifloxacin	Vilanterol may increase the QTc-prolonging activities of Gemifloxacin.	Approved, Investigational
Goserelin	Vilanterol may increase the QTc-prolonging activities of Goserelin.	Approved
Granisetron	Vilanterol may increase the QTc-prolonging activities of Granisetron.	Approved, Investigational
Haloperidol	Vilanterol may increase the QTc-prolonging activities of Haloperidol.	Approved
Hydracarbazine	The risk or severity of adverse effects can be increased when Hydracarbazine is combined with Vilanterol.	Experimental
Hydrochlorothiazide	Vilanterol may increase the hypokalemic activities of Hydrochlorothiazide.	Approved, Vet Approved
Hydroflumethiazide	Vilanterol may increase the hypokalemic activities of Hydroflumethiazide.	Approved
Ibutilide	Vilanterol may increase the QTc-prolonging activities of Ibutilide.	Approved
Idelalisib	The serum concentration of Vilanterol can be increased when it is combined with Idelalisib.	Approved
Iloperidone	Vilanterol may increase the QTc-prolonging activities of Iloperidone.	Approved
Imatinib	The metabolism of Vilanterol can be decreased when combined with Imatinib.	Approved
Imipramine	The risk or severity of adverse effects can be increased when Imipramine is combined with Vilanterol.	Approved
Indapamide	Vilanterol may increase the hypokalemic activities of Indapamide.	Approved
Indinavir	The metabolism of Vilanterol can be decreased when combined with Indinavir.	Approved
INGN 201	The risk or severity of adverse effects can be increased when Vilanterol is combined with INGN 201.	Investigational
INGN 225	The risk or severity of adverse effects can be increased when Vilanterol is combined with INGN 225.	Investigational
Iproclozide	The risk or severity of adverse effects can be increased when Iproclozide is combined with Vilanterol.	Withdrawn
Iproniazid	The risk or severity of adverse effects can be increased when Iproniazid is combined with Vilanterol.	Withdrawn
Isavuconazonium	The metabolism of Vilanterol can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isocarboxazid	The risk or severity of adverse effects can be increased when Isocarboxazid is combined with Vilanterol.	Approved
Isradipine	The metabolism of Vilanterol can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Vilanterol can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Vilanterol can be increased when it is combined with Ivacaftor.	Approved
Ketoconazole	The metabolism of Vilanterol can be decreased when combined with Ketoconazole.	Approved, Investigational
Leflunomide	The risk or severity of adverse effects can be increased when Vilanterol is combined with Leflunomide.	Approved, Investigational
Lenvatinib	Vilanterol may increase the QTc-prolonging activities of Lenvatinib.	Approved
Leuprolide	Vilanterol may increase the QTc-prolonging activities of Leuprolide.	Approved, Investigational
Levofloxacin	Vilanterol may increase the QTc-prolonging activities of Levofloxacin.	Approved, Investigational
Lopinavir	The metabolism of Vilanterol can be decreased when combined with Lopinavir.	Approved
Lovastatin	The metabolism of Vilanterol can be decreased when combined with Lovastatin.	Approved, Investigational
Loxapine	The risk or severity of adverse effects can be increased when Vilanterol is combined with Loxapine.	Approved
Luliconazole	The serum concentration of Vilanterol can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Vilanterol can be increased when combined with Lumacaftor.	Approved
Lumefantrine	Vilanterol may increase the QTc-prolonging activities of Lumefantrine.	Approved
Mebanazine	The risk or severity of adverse effects can be increased when Mebanazine is combined with Vilanterol.	Withdrawn
Methadone	Vilanterol may increase the QTc-prolonging activities of Methadone.	Approved
Methyclothiazide	Vilanterol may increase the hypokalemic activities of Methyclothiazide.	Approved
Methylene blue	The risk or severity of adverse effects can be increased when Methylene blue is combined with Vilanterol.	Investigational
Metolazone	Vilanterol may increase the hypokalemic activities of Metolazone.	Approved
Metoprolol	Metoprolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Investigational
Mifepristone	Mifepristone may increase the QTc-prolonging activities of Vilanterol.	Approved, Investigational
Minaprine	The risk or severity of adverse effects can be increased when Minaprine is combined with Vilanterol.	Approved
Mirtazapine	The risk or severity of adverse effects can be increased when Mirtazapine is combined with Vilanterol.	Approved
Mitotane	The serum concentration of Vilanterol can be decreased when it is combined with Mitotane.	Approved
Moclobemide	The risk or severity of adverse effects can be increased when Moclobemide is combined with Vilanterol.	Approved
Modafinil	The serum concentration of Vilanterol can be decreased when it is combined with Modafinil.	Approved, Investigational
Moxifloxacin	Vilanterol may increase the QTc-prolonging activities of Moxifloxacin.	Approved, Investigational
Nadolol	Nadolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Nafcillin	The serum concentration of Vilanterol can be decreased when it is combined with Nafcillin.	Approved
Natalizumab	The risk or severity of adverse effects can be increased when Vilanterol is combined with Natalizumab.	Approved, Investigational
Nebivolol	Nebivolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Investigational
Nefazodone	The metabolism of Vilanterol can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Vilanterol can be decreased when combined with Nelfinavir.	Approved
Netupitant	The serum concentration of Vilanterol can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Vilanterol can be increased when combined with Nevirapine.	Approved
Nialamide	The risk or severity of adverse effects can be increased when Nialamide is combined with Vilanterol.	Withdrawn
Nilotinib	Vilanterol may increase the QTc-prolonging activities of Nilotinib.	Approved, Investigational
Nortriptyline	The risk or severity of adverse effects can be increased when Nortriptyline is combined with Vilanterol.	Approved
Octamoxin	The risk or severity of adverse effects can be increased when Octamoxin is combined with Vilanterol.	Withdrawn
Ofloxacin	Vilanterol may increase the QTc-prolonging activities of Ofloxacin.	Approved
Olaparib	The metabolism of Vilanterol can be decreased when combined with Olaparib.	Approved
Ondansetron	Vilanterol may increase the QTc-prolonging activities of Ondansetron.	Approved
Opipramol	The risk or severity of adverse effects can be increased when Opipramol is combined with Vilanterol.	Investigational
Osimertinib	The serum concentration of Vilanterol can be increased when it is combined with Osimertinib.	Approved
Oxprenolol	Oxprenolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Palbociclib	The serum concentration of Vilanterol can be increased when it is combined with Palbociclib.	Approved
Paliperidone	Vilanterol may increase the QTc-prolonging activities of Paliperidone.	Approved
Panobinostat	Vilanterol may increase the QTc-prolonging activities of Panobinostat.	Approved, Investigational
Pargyline	The risk or severity of adverse effects can be increased when Pargyline is combined with Vilanterol.	Approved
Pazopanib	Vilanterol may increase the QTc-prolonging activities of Pazopanib.	Approved
Penbutolol	Penbutolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Investigational
Pentamidine	Vilanterol may increase the QTc-prolonging activities of Pentamidine.	Approved
Pentobarbital	The metabolism of Vilanterol can be increased when combined with Pentobarbital.	Approved, Vet Approved
Perflutren	Vilanterol may increase the QTc-prolonging activities of Perflutren.	Approved
Phenelzine	The risk or severity of adverse effects can be increased when Phenelzine is combined with Vilanterol.	Approved
Pheniprazine	The risk or severity of adverse effects can be increased when Pheniprazine is combined with Vilanterol.	Withdrawn
Phenobarbital	The metabolism of Vilanterol can be increased when combined with Phenobarbital.	Approved
Phenoxypropazine	The risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Vilanterol.	Withdrawn
Phenytoin	The metabolism of Vilanterol can be increased when combined with Phenytoin.	Approved, Vet Approved
Pimecrolimus	The risk or severity of adverse effects can be increased when Pimecrolimus is combined with Vilanterol.	Approved, Investigational
Pimozide	Vilanterol may increase the QTc-prolonging activities of Pimozide.	Approved
Pindolol	Pindolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Piretanide	Vilanterol may increase the hypokalemic activities of Piretanide.	Experimental
Pirlindole	The risk or severity of adverse effects can be increased when Pirlindole is combined with Vilanterol.	Approved
Pivhydrazine	The risk or severity of adverse effects can be increased when Pivhydrazine is combined with Vilanterol.	Withdrawn
Polythiazide	Vilanterol may increase the hypokalemic activities of Polythiazide.	Approved
Posaconazole	The metabolism of Vilanterol can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Primaquine	Vilanterol may increase the QTc-prolonging activities of Primaquine.	Approved
Primidone	The metabolism of Vilanterol can be increased when combined with Primidone.	Approved, Vet Approved
Procainamide	Vilanterol may increase the QTc-prolonging activities of Procainamide.	Approved
Promazine	Vilanterol may increase the QTc-prolonging activities of Promazine.	Approved, Vet Approved
Propafenone	Vilanterol may increase the QTc-prolonging activities of Propafenone.	Approved
Propranolol	Propranolol may decrease the bronchodilatory activities of Vilanterol.	Approved, Investigational
Protriptyline	The risk or severity of adverse effects can be increased when Protriptyline is combined with Vilanterol.	Approved
Quetiapine	Vilanterol may increase the QTc-prolonging activities of Quetiapine.	Approved
Quinethazone	Vilanterol may increase the hypokalemic activities of Quinethazone.	Approved
Quinidine	Vilanterol may increase the QTc-prolonging activities of Quinidine.	Approved
Quinine	Vilanterol may increase the QTc-prolonging activities of Quinine.	Approved
Ranolazine	The metabolism of Vilanterol can be decreased when combined with Ranolazine.	Approved, Investigational
Rasagiline	The risk or severity of adverse effects can be increased when Rasagiline is combined with Vilanterol.	Approved
Rifabutin	The metabolism of Vilanterol can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Vilanterol can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Vilanterol can be increased when combined with Rifapentine.	Approved
Rindopepimut	The risk or severity of adverse effects can be increased when Vilanterol is combined with CDX-110.	Investigational
Ritonavir	The metabolism of Vilanterol can be decreased when combined with Ritonavir.	Approved, Investigational
Roflumilast	Roflumilast may increase the immunosuppressive activities of Vilanterol.	Approved
Safrazine	The risk or severity of adverse effects can be increased when Safrazine is combined with Vilanterol.	Withdrawn
Saquinavir	The metabolism of Vilanterol can be decreased when combined with Saquinavir.	Approved, Investigational
Selegiline	The risk or severity of adverse effects can be increased when Selegiline is combined with Vilanterol.	Approved, Investigational, Vet Approved
Sildenafil	The metabolism of Vilanterol can be decreased when combined with Sildenafil.	Approved, Investigational
Siltuximab	The serum concentration of Vilanterol can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Vilanterol can be increased when it is combined with Simeprevir.	Approved
Sipuleucel-T	The therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Vilanterol.	Approved
Sotalol	Sotalol may decrease the bronchodilatory activities of Vilanterol.	Approved
SRP 299	The risk or severity of adverse effects can be increased when Vilanterol is combined with SRP 299.	Investigational
St. John's Wort	The serum concentration of Vilanterol can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Vilanterol can be increased when it is combined with Stiripentol.	Approved
Sulfisoxazole	Vilanterol may increase the QTc-prolonging activities of Sulfisoxazole.	Approved, Vet Approved
Tacrolimus	The risk or severity of adverse effects can be increased when Tacrolimus is combined with Vilanterol.	Approved, Investigational
Telaprevir	The metabolism of Vilanterol can be decreased when combined with Telaprevir.	Withdrawn
Telavancin	Vilanterol may increase the QTc-prolonging activities of Telavancin.	Approved
Telithromycin	The metabolism of Vilanterol can be decreased when combined with Telithromycin.	Approved
Tetrabenazine	Vilanterol may increase the QTc-prolonging activities of Tetrabenazine.	Approved
Thioridazine	Vilanterol may increase the QTc-prolonging activities of Thioridazine.	Withdrawn
Tianeptine	The risk or severity of adverse effects can be increased when Tianeptine is combined with Vilanterol.	Approved
Ticlopidine	The metabolism of Vilanterol can be decreased when combined with Ticlopidine.	Approved
Timolol	Timolol may decrease the bronchodilatory activities of Vilanterol.	Approved
Tocilizumab	The serum concentration of Vilanterol can be decreased when it is combined with Tocilizumab.	Approved
Tofacitinib	Vilanterol may increase the immunosuppressive activities of Tofacitinib.	Approved, Investigational
Toloxatone	The risk or severity of adverse effects can be increased when Toloxatone is combined with Vilanterol.	Approved
Torasemide	Vilanterol may increase the hypokalemic activities of Torasemide.	Approved
Toremifene	Vilanterol may increase the QTc-prolonging activities of Toremifene.	Approved, Investigational
Trans-2-Phenylcyclopropylamine	The risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Vilanterol.	Experimental
Tranylcypromine	The risk or severity of adverse effects can be increased when Tranylcypromine is combined with Vilanterol.	Approved
Trastuzumab	Trastuzumab may increase the neutropenic activities of Vilanterol.	Approved, Investigational
Trichlormethiazide	Vilanterol may increase the hypokalemic activities of Trichlormethiazide.	Approved, Vet Approved
Trimipramine	The risk or severity of adverse effects can be increased when Trimipramine is combined with Vilanterol.	Approved
Vandetanib	Vilanterol may increase the QTc-prolonging activities of Vandetanib.	Approved
Vemurafenib	Vilanterol may increase the QTc-prolonging activities of Vemurafenib.	Approved
Venlafaxine	The metabolism of Vilanterol can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Vilanterol can be decreased when combined with Verapamil.	Approved
Voriconazole	The metabolism of Vilanterol can be decreased when combined with Voriconazole.	Approved, Investigational
Ziprasidone	Vilanterol may increase the QTc-prolonging activities of Ziprasidone.	Approved
Zuclopenthixol	Vilanterol may increase the QTc-prolonging activities of Zuclopenthixol.	Approved, Investigational

Food Interactions

Not Available

References

Synthesis Reference

Not Available

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

Resource	Link
KEGG Drug	D10501
ChemSpider	8360167
BindingDB	50416060
ChEBI	75037
ChEMBL	CHEMBL1198857
Drug Product Database	22120
RxList	http://www.rxlist.com/breo-ellipta-drug.htm
Drugs.com	http://www.drugs.com/breo-ellipta.html
Wikipedia	Vilanterol

ATC Codes

R03AK10 — Vilanterol and fluticasone furoate

R03AL03 — Vilanterol and umeclidinium bromide

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (12.2 MB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Asthma Bronchial	1
1	Completed	Not Available	Healthy Volunteers / Pulmonary Disease, Chronic Obstructive	1
1	Completed	Basic Science	Asthma Bronchial	1
1	Completed	Other	Asthma Bronchial	1
1	Completed	Other	Pulmonary Disease, Chronic Obstructive	1
1	Completed	Prevention	Healthy Volunteers / Pulmonary Disease, Chronic Obstructive	1
1	Completed	Treatment	Asthma Bronchial / Healthy Volunteers	2
1	Completed	Treatment	Asthma Bronchial / Pulmonary Disease, Chronic Obstructive	2
1	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive	1
1	Completed	Treatment	Healthy Volunteers / Pulmonary Disease, Chronic Obstructive	2
1	Completed	Treatment	Pulmonary Disease, Chronic Obstructive	3
2	Completed	Treatment	Asthma Bronchial	6
2	Completed	Treatment	Asthma Bronchial / Pulmonary Disease, Chronic Obstructive	2
2	Completed	Treatment	Pulmonary Disease, Chronic Obstructive	7
2	Recruiting	Diagnostic	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Active Not Recruiting	Treatment	Pulmonary Disease, Chronic Obstructive	1
3	Completed	Not Available	Pulmonary Disease, Chronic Obstructive	1
3	Completed	Treatment	Asthma Bronchial	4
3	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	3
3	Completed	Treatment	Pulmonary Disease, Chronic Obstructive	13
3	Recruiting	Treatment	Asthma Bronchial	1
3	Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Active Not Recruiting	Treatment	Pulmonary Disease, Chronic Obstructive	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)
US5873360	Yes	1996-08-23	2016-08-23	US
US7101866	No	2001-08-03	2021-08-03	US
US7439393	No	2002-09-11	2022-09-11	US
US6759398	No	2001-08-03	2021-08-03	US
USRE44874	No	2003-03-23	2023-03-23	US
US6537983	No	2001-08-03	2021-08-03	US
US8511304	No	2007-06-14	2027-06-14	US
US7629335	No	2001-08-03	2021-08-03	US
US8161968	No	2008-02-05	2028-02-05	US
US8746242	No	2010-10-11	2030-10-11	US
US8113199	No	2007-10-23	2027-10-23	US
US7776895	No	2002-09-11	2022-09-11	US
US8534281	No	2009-08-10	2029-08-10	US
US6878698	No	2001-08-03	2021-08-03	US
US8309572	No	2005-04-27	2025-04-27	US
US8183257	No	2005-07-27	2025-07-27	US
US7488827	No	2005-04-27	2025-04-27	US
US7498440	No	2005-04-27	2025-04-27	US
US9333310	No	2007-10-02	2027-10-02	US

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	53.12 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 Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	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 / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Primary alcohols / Organochlorides

Substituents

Benzylether / Benzyl alcohol / 1,3-dichlorobenzene / Aralkylamine / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / 1,2-aminoalcohol / Secondary alcohol

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

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

Targets

Details

1. Beta-2 adrenergic receptor

Kind: Protein
Organism: Human
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 30-fold greater affinity than it does norepinephrine.
Gene Name:: ADRB2
Uniprot ID:: P07550
Uniprot Name:: Beta-2 adrenergic receptor
Molecular Weight:: 46458.32 Da

Enzymes

Details

1. Cytochrome P450 3A4

Kind: Protein
Organism: Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
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 August 08, 2017 11:11

Structure for DB09082 (Vilanterol)

Targets

Enzymes