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
Thumb
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
IngredientUNIICASInChI Key
Vilanterol Trifenatate40AHO2C6DG503070-58-4KLOLZALDXGTNQE-JIDHJSLPSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AnoroVilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
AnoroVilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
AnoroVilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
Anoro ElliptaVilanterol (25 mcg) + Umeclidinium (62.5 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2014-03-14Not applicableCanada
Anoro ElliptaVilanterol Trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2014-01-31Not applicableUs
Breo ElliptaVilanterol (25 mcg) + Fluticasone furoate (100 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2013-11-29Not applicableCanada
Breo ElliptaVilanterol Trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2013-08-26Not applicableUs
Breo ElliptaVilanterol Trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2015-04-30Not applicableUs
Breo ElliptaVilanterol Trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1)PowderRespiratory (inhalation)A S Medication Solutions2015-04-302017-06-20Us
Breo ElliptaVilanterol (25 mcg) + Fluticasone furoate (200 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2015-10-02Not applicableCanada
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][[email protected]](O)(CNCCCCCCOCCOCC1=C(Cl)C=CC=C1Cl)C1=CC(CO)=C(O)C=C1

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.

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.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Human
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
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Vilanterol.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Vilanterol.Approved
AlprenololAlprenolol may decrease the bronchodilatory activities of Vilanterol.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Vilanterol.Illicit, Withdrawn
AmiodaroneThe metabolism of Vilanterol can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Vilanterol.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Vilanterol.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Vilanterol.Approved, Illicit
AnagrelideVilanterol may increase the QTc-prolonging activities of Anagrelide.Approved
AprepitantThe serum concentration of Vilanterol can be increased when it is combined with Aprepitant.Approved, Investigational
Arsenic trioxideVilanterol may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherVilanterol may increase the QTc-prolonging activities of Artemether.Approved
AsenapineVilanterol may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirThe metabolism of Vilanterol can be decreased when combined with Atazanavir.Approved, Investigational
AtenololAtenolol may decrease the bronchodilatory activities of Vilanterol.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Vilanterol.Approved
AtosibanThe risk or severity of adverse effects can be increased when Vilanterol is combined with Atosiban.Approved, Investigational
AzithromycinVilanterol may increase the QTc-prolonging activities of Azithromycin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Vilanterol.Investigational
BedaquilineVilanterol may increase the QTc-prolonging activities of Bedaquiline.Approved
BendroflumethiazideVilanterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Vilanterol.Withdrawn
BetahistineThe therapeutic efficacy of Vilanterol can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Vilanterol.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Vilanterol.Approved
BoceprevirThe metabolism of Vilanterol can be decreased when combined with Boceprevir.Approved, Withdrawn
BopindololBopindolol may decrease the bronchodilatory activities of Vilanterol.Approved
BortezomibThe metabolism of Vilanterol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Vilanterol can be decreased when it is combined with Bosentan.Approved, Investigational
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Vilanterol.Experimental
BumetanideVilanterol may increase the hypokalemic activities of Bumetanide.Approved
BupranololBupranolol may decrease the bronchodilatory activities of Vilanterol.Approved
CarbamazepineThe metabolism of Vilanterol can be increased when combined with Carbamazepine.Approved, Investigational
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Vilanterol.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Vilanterol.Approved
CeliprololCeliprolol may decrease the bronchodilatory activities of Vilanterol.Approved, Investigational
CeritinibThe serum concentration of Vilanterol can be increased when it is combined with Ceritinib.Approved
ChloroquineVilanterol may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorothiazideVilanterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineVilanterol may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorthalidoneVilanterol may increase the hypokalemic activities of Chlorthalidone.Approved
CiprofloxacinVilanterol may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideVilanterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramVilanterol may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinThe metabolism of Vilanterol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Vilanterol can be decreased when combined with Clemastine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Vilanterol.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Vilanterol.Experimental
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Vilanterol.Approved
ClotrimazoleThe metabolism of Vilanterol can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineVilanterol may increase the QTc-prolonging activities of Clozapine.Approved
CobicistatThe metabolism of Vilanterol can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Vilanterol can be increased when it is combined with Conivaptan.Approved, Investigational
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with Vilanterol.Approved
CrizotinibVilanterol may increase the QTc-prolonging activities of Crizotinib.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Vilanterol.Approved
CyclopenthiazideVilanterol may increase the hypokalemic activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Vilanterol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Vilanterol can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Vilanterol can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Vilanterol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Vilanterol can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Vilanterol can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Vilanterol.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Vilanterol.Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Vilanterol.Experimental
DihydroergotamineThe metabolism of Vilanterol can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Vilanterol can be decreased when combined with Diltiazem.Approved
DisopyramideVilanterol may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideVilanterol may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronVilanterol may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneVilanterol may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Vilanterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Vilanterol.Approved
DoxycyclineThe metabolism of Vilanterol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneVilanterol may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolVilanterol may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
EliglustatVilanterol may increase the QTc-prolonging activities of Eliglustat.Approved
EnzalutamideThe serum concentration of Vilanterol can be decreased when it is combined with Enzalutamide.Approved
ErythromycinVilanterol may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramVilanterol may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Vilanterol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Vilanterol.Approved
Etacrynic acidVilanterol may increase the hypokalemic activities of Etacrynic acid.Approved
FingolimodVilanterol may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FlecainideVilanterol may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluconazoleThe metabolism of Vilanterol can be decreased when combined with Fluconazole.Approved
FluoxetineVilanterol may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolVilanterol may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvoxamineThe metabolism of Vilanterol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Vilanterol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Vilanterol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Vilanterol can be increased when combined with Fosphenytoin.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Vilanterol.Approved, Investigational, Vet Approved
FurosemideVilanterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Vilanterol can be increased when it is combined with Fusidic Acid.Approved
G17DTThe therapeutic efficacy of G17DT can be decreased when used in combination with Vilanterol.Investigational
Gadobenic acidVilanterol may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemifloxacinVilanterol may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with Vilanterol.Investigational
GoserelinVilanterol may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronVilanterol may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolVilanterol may increase the QTc-prolonging activities of Haloperidol.Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Vilanterol.Experimental
Hepatitis A VaccineThe therapeutic efficacy of Hepatitis A Vaccine can be decreased when used in combination with Vilanterol.Approved
Hepatitis B Vaccine (Recombinant)The therapeutic efficacy of Hepatitis B Vaccine (Recombinant) can be decreased when used in combination with Vilanterol.Approved, Withdrawn
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Vilanterol.Experimental
HydrochlorothiazideVilanterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideVilanterol may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
IbutilideVilanterol may increase the QTc-prolonging activities of Ibutilide.Approved
IloperidoneVilanterol may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Vilanterol can be decreased when combined with Imatinib.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Vilanterol.Approved
IndapamideVilanterol may increase the hypokalemic activities of Indapamide.Approved
IndinavirThe metabolism of Vilanterol can be decreased when combined with Indinavir.Approved
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with Vilanterol.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with Vilanterol.Investigational
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Vilanterol.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Vilanterol.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Vilanterol.Withdrawn
IsavuconazoniumThe metabolism of Vilanterol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Vilanterol.Approved
IsradipineThe metabolism of Vilanterol can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Vilanterol can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Vilanterol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Vilanterol can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Vilanterol is combined with Leflunomide.Approved, Investigational
LenvatinibVilanterol may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideVilanterol may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinVilanterol may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Vilanterol.Experimental
LopinavirThe metabolism of Vilanterol can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Vilanterol can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Vilanterol is combined with Loxapine.Approved
LuliconazoleThe serum concentration of Vilanterol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Vilanterol can be increased when combined with Lumacaftor.Approved
LumefantrineVilanterol may increase the QTc-prolonging activities of Lumefantrine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Vilanterol.Withdrawn
MepindololMepindolol may decrease the bronchodilatory activities of Vilanterol.Experimental
MethadoneVilanterol may increase the QTc-prolonging activities of Methadone.Approved
MethyclothiazideVilanterol may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Vilanterol.Approved, Investigational
MetolazoneVilanterol may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Vilanterol.Approved, Investigational
MifepristoneMifepristone may increase the QTc-prolonging activities of Vilanterol.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Vilanterol.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Vilanterol.Approved
MitotaneThe serum concentration of Vilanterol can be decreased when it is combined with Mitotane.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Vilanterol.Approved
MoxifloxacinVilanterol may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Vilanterol is combined with Natalizumab.Approved, Investigational
NebivololNebivolol may decrease the bronchodilatory activities of Vilanterol.Approved, Investigational
NefazodoneThe metabolism of Vilanterol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Vilanterol can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Vilanterol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Vilanterol can be increased when combined with Nevirapine.Approved
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Vilanterol.Withdrawn
NilotinibVilanterol may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Vilanterol.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Vilanterol.Withdrawn
OfloxacinVilanterol may increase the QTc-prolonging activities of Ofloxacin.Approved
OlaparibThe metabolism of Vilanterol can be decreased when combined with Olaparib.Approved
OndansetronVilanterol may increase the QTc-prolonging activities of Ondansetron.Approved
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Vilanterol.Investigational
OsimertinibThe serum concentration of Vilanterol can be increased when it is combined with Osimertinib.Approved
OxprenololOxprenolol may decrease the bronchodilatory activities of Vilanterol.Approved
PalbociclibThe serum concentration of Vilanterol can be increased when it is combined with Palbociclib.Approved
PaliperidoneVilanterol may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatVilanterol may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Vilanterol.Approved
PazopanibVilanterol may increase the QTc-prolonging activities of Pazopanib.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Vilanterol.Approved, Investigational
PentamidineVilanterol may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe metabolism of Vilanterol can be increased when combined with Pentobarbital.Approved, Vet Approved
PerflutrenVilanterol may increase the QTc-prolonging activities of Perflutren.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Vilanterol.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Vilanterol.Withdrawn
PhenobarbitalThe metabolism of Vilanterol can be increased when combined with Phenobarbital.Approved
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Vilanterol.Withdrawn
PhenytoinThe metabolism of Vilanterol can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Vilanterol.Approved, Investigational
PimozideVilanterol may increase the QTc-prolonging activities of Pimozide.Approved
PiretanideVilanterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Vilanterol.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Vilanterol.Withdrawn
PolythiazideVilanterol may increase the hypokalemic activities of Polythiazide.Approved
PosaconazoleThe metabolism of Vilanterol can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimaquineVilanterol may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Vilanterol can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideVilanterol may increase the QTc-prolonging activities of Procainamide.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Vilanterol.Approved
PromazineVilanterol may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneVilanterol may increase the QTc-prolonging activities of Propafenone.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Vilanterol.Approved
QuetiapineVilanterol may increase the QTc-prolonging activities of Quetiapine.Approved
QuinethazoneVilanterol may increase the hypokalemic activities of Quinethazone.Approved
QuinidineVilanterol may increase the QTc-prolonging activities of Quinidine.Approved
QuinineVilanterol may increase the QTc-prolonging activities of Quinine.Approved
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when Vilanterol is combined with Rabies virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Vilanterol.Approved
RanolazineThe metabolism of Vilanterol can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Vilanterol.Approved
RifabutinThe metabolism of Vilanterol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Vilanterol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Vilanterol can be increased when combined with Rifapentine.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with Vilanterol.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Vilanterol.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with Vilanterol.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Vilanterol.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Vilanterol.Withdrawn
Salmonella typhi ty21a live antigenThe therapeutic efficacy of Salmonella typhi ty21a live antigen can be decreased when used in combination with Vilanterol.Approved
SaquinavirThe metabolism of Vilanterol can be decreased when combined with Saquinavir.Approved, Investigational
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Vilanterol.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Vilanterol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Vilanterol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Vilanterol can be increased when it is combined with Simeprevir.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Vilanterol.Approved
SotalolVilanterol may increase the QTc-prolonging activities of Sotalol.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with Vilanterol.Investigational
St. John's WortThe serum concentration of Vilanterol can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Vilanterol can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleVilanterol may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Vilanterol.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with Vilanterol.Investigational
TelaprevirThe metabolism of Vilanterol can be decreased when combined with Telaprevir.Approved, Withdrawn
TelavancinVilanterol may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinThe metabolism of Vilanterol can be decreased when combined with Telithromycin.Approved
TertatololTertatolol may decrease the bronchodilatory activities of Vilanterol.Experimental
TetrabenazineVilanterol may increase the QTc-prolonging activities of Tetrabenazine.Approved
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with Vilanterol.Investigational
ThioridazineVilanterol may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Vilanterol.Approved, Investigational
TiclopidineThe metabolism of Vilanterol can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Vilanterol can be decreased when it is combined with Tocilizumab.Approved
TofacitinibVilanterol may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Vilanterol.Approved
TorasemideVilanterol may increase the hypokalemic activities of Torasemide.Approved
ToremifeneVilanterol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Vilanterol.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Vilanterol.Approved
TrastuzumabTrastuzumab may increase the neutropenic activities of Vilanterol.Approved, Investigational
TrichlormethiazideVilanterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Vilanterol.Approved
VandetanibVilanterol may increase the QTc-prolonging activities of Vandetanib.Approved
Varicella Zoster Vaccine (Live/Attenuated)The therapeutic efficacy of Zoster vaccine can be decreased when used in combination with Vilanterol.Approved
VemurafenibVilanterol may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineThe metabolism of Vilanterol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Vilanterol can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Vilanterol can be decreased when combined with Voriconazole.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with Vilanterol.Approved
ZiprasidoneVilanterol may increase the QTc-prolonging activities of Ziprasidone.Approved
ZuclopenthixolVilanterol may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

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
D10501
PubChem Compound
10184665
PubChem Substance
347827825
ChemSpider
8360167
BindingDB
50416060
ChEBI
75037
ChEMBL
CHEMBL1198857
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vilanterol
ATC Codes
R03AK10 — Vilanterol and fluticasone furoateR03AL03 — Vilanterol and umeclidinium bromide
FDA label
Download (12.2 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableAsthma Bronchial1
1CompletedNot AvailableHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
1CompletedBasic ScienceAsthma Bronchial1
1CompletedOtherAsthma Bronchial1
1CompletedOtherPulmonary Disease, Chronic Obstructive1
1CompletedPreventionHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentAsthma Bronchial / Healthy Volunteers2
1CompletedTreatmentAsthma Bronchial / Pulmonary Disease, Chronic Obstructive2
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentHealthy Volunteers / Pulmonary Disease, Chronic Obstructive2
1CompletedTreatmentPulmonary Disease, Chronic Obstructive3
2CompletedTreatmentAsthma Bronchial6
2CompletedTreatmentAsthma Bronchial / Pulmonary Disease, Chronic Obstructive2
2CompletedTreatmentPulmonary Disease, Chronic Obstructive7
2RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedOtherPulmonary Disease, Chronic Obstructive1
3CompletedTreatmentAsthma Bronchial5
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)3
3CompletedTreatmentPulmonary Disease, Chronic Obstructive14
4Active Not RecruitingTreatmentPulmonary Disease, Chronic Obstructive1
4RecruitingTreatmentAsthma Bronchial1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Powder, meteredRespiratory (inhalation)
PowderRespiratory (inhalation)
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5873360Yes1996-08-232016-08-23Us
US7101866No2001-08-032021-08-03Us
US7439393No2002-09-112022-09-11Us
US6759398No2001-08-032021-08-03Us
USRE44874No2003-03-232023-03-23Us
US6537983No2001-08-032021-08-03Us
US8511304No2007-06-142027-06-14Us
US7629335No2001-08-032021-08-03Us
US8161968No2008-02-052028-02-05Us
US8746242No2010-10-112030-10-11Us
US8113199No2007-10-232027-10-23Us
US7776895No2002-09-112022-09-11Us
US8534281No2009-08-102029-08-10Us
US6878698No2001-08-032021-08-03Us
US8309572No2005-04-272025-04-27Us
US8183257No2005-07-272025-07-27Us
US7488827No2005-04-272025-04-27Us
US7498440No2005-04-272025-04-27Us
US9333310No2007-10-022027-10-02Us
US9750726No2010-11-292030-11-29Us
US9750762No2010-11-292030-11-29Us

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
Polarizability53.12 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

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
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da

Enzymes

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 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 December 01, 2017 17:20