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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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 DB09082 (Vilanterol)
- 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 Vilanterol Trifenatate 40AHO2C6DG 503070-58-4 KLOLZALDXGTNQE-JIDHJSLPSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Anoro Vilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxo Group Limited 2014-05-08 Not applicable EU 
Anoro Vilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxo Group Limited 2014-05-08 Not applicable EU Anoro Vilanterol Trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxo Group Limited 2014-05-08 Not applicable EU Anoro Ellipta Vilanterol Trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1) Powder Respiratory (inhalation) Glaxosmithkline Inc 2014-01-31 Not applicable US 
Anoro Ellipta Vilanterol (25 mcg) + Umeclidinium (62.5 mcg) Powder Respiratory (inhalation) Glaxosmithkline Inc 2014-03-14 Not applicable Canada 
Breo Ellipta Vilanterol Trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1) Powder Respiratory (inhalation) Remedy Repack 2016-04-04 2017-03-16 US Breo Ellipta Vilanterol Trifenatate (25 ug/1) + Fluticasone furoate (100 ug/1) Powder Respiratory (inhalation) Glaxosmithkline Inc 2013-08-26 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 Trifenatate (25 ug/1) + Fluticasone furoate (200 ug/1) Powder Respiratory (inhalation) Glaxosmithkline Inc 2015-04-30 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 2017-06-20 US - Categories
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics, Inhalants
- Agents to Treat Airway Disease
- Alcohols
- Benzene Derivatives
- Benzyl Compounds
- Drugs for Obstructive Airway Diseases
- 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
- [H][C@](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.
- 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 agonistHuman - 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
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, Investigational Acepromazine Acepromazine may decrease the vasoconstricting activities of Vilanterol. Approved, Vet Approved Acetyl sulfisoxazole The metabolism of Vilanterol can be decreased when combined with Acetyl sulfisoxazole. Approved, Vet Approved Alfuzosin Alfuzosin may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational 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 Amitriptylinoxide The risk or severity of adverse effects can be increased when Amitriptylinoxide is combined with Vilanterol. Approved, Investigational Amoxapine The therapeutic efficacy of Vilanterol can be decreased when used in combination with Amoxapine. Approved Amphetamine The risk or severity of adverse effects can be increased when Amphetamine is combined with Vilanterol. Approved, Illicit, Investigational Anagrelide Vilanterol may increase the QTc-prolonging activities of Anagrelide. Approved Anthrax immune globulin human The risk or severity of adverse effects can be increased when Vilanterol is combined with Anthrax immune globulin human. Approved Apalutamide The serum concentration of Vilanterol can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Vilanterol can be increased when it is combined with Aprepitant. Approved, Investigational Aripiprazole Aripiprazole may decrease the vasoconstricting activities of Vilanterol. 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 Atosiban The risk or severity of adverse effects can be increased when Vilanterol is combined with Atosiban. Approved, Investigational Azithromycin Vilanterol may increase the QTc-prolonging activities of Azithromycin. Approved Azosemide Vilanterol may increase the hypokalemic activities of Azosemide. Investigational Bacillus calmette-guerin substrain connaught live antigen The risk or severity of adverse effects can be increased when Vilanterol is combined with Bacillus calmette-guerin substrain connaught live antigen. Approved, Investigational Bacillus calmette-guerin substrain tice live antigen The risk or severity of adverse effects can be increased when Vilanterol is combined with Bacillus calmette-guerin substrain tice live antigen. Approved BCG vaccine The therapeutic efficacy of BCG vaccine 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 Benzthiazide Vilanterol may increase the hypokalemic activities of Benzthiazide. Approved Benzylpenicilloyl Polylysine Vilanterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent. Approved Betahistine The therapeutic efficacy of Vilanterol can be decreased when used in combination with Betahistine. Approved, Investigational Betaxolol Betaxolol may decrease the bronchodilatory activities of Vilanterol. Approved, Investigational Bevantolol Bevantolol may decrease the vasoconstricting activities of Vilanterol. Approved Bisoprolol Bisoprolol may decrease the bronchodilatory activities of Vilanterol. Approved Boceprevir The metabolism of Vilanterol can be decreased when combined with Boceprevir. Approved, 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 Brexpiprazole Brexpiprazole may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Brofaromine The risk or severity of adverse effects can be increased when Brofaromine is combined with Vilanterol. Experimental Bromocriptine Bromocriptine may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved, Investigational Bucindolol Bucindolol may decrease the vasoconstricting activities of Vilanterol. Investigational Bumetanide Vilanterol may increase the hypokalemic activities of Bumetanide. Approved Bunazosin Bunazosin may decrease the vasoconstricting activities of Vilanterol. Investigational Bupranolol Bupranolol may decrease the bronchodilatory activities of Vilanterol. Approved Butriptyline The risk or severity of adverse effects can be increased when Butriptyline is combined with Vilanterol. Approved Cabergoline Cabergoline may increase the hypertensive and vasoconstricting 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 Carvedilol Carvedilol may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational 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, Investigational, 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, Investigational, 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, Investigational Clomipramine The risk or severity of adverse effects can be increased when Clomipramine is combined with Vilanterol. Approved, Investigational, Vet Approved Cloranolol Cloranolol may decrease the bronchodilatory activities of Vilanterol. Experimental Clostridium tetani toxoid antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Vilanterol is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated). 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 Conivaptan can be increased when it is combined with Vilanterol. Approved, Investigational Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Vilanterol is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated). Approved Crizotinib The metabolism of Vilanterol can be decreased when combined with Crizotinib. Approved Curcumin The metabolism of Vilanterol can be decreased when combined with Curcumin. Approved, Investigational Cyclopenthiazide Vilanterol may increase the hypokalemic activities of Cyclopenthiazide. Experimental 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, Investigational Dapiprazole Dapiprazole may decrease the vasoconstricting activities of Vilanterol. 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, Investigational Desvenlafaxine Desvenlafaxine may increase the tachycardic activities of Vilanterol. Approved, Investigational Dextroamphetamine Dextroamphetamine may decrease the vasoconstricting activities of Vilanterol. Approved, Illicit Dibenzepin The risk or severity of adverse effects can be increased when Dibenzepin is combined with Vilanterol. Experimental Dihydroergotamine Dihydroergotamine may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved, Investigational Diltiazem The metabolism of Vilanterol can be decreased when combined with Diltiazem. Approved, Investigational Dimetacrine The risk or severity of adverse effects can be increased when Dimetacrine is combined with Vilanterol. Approved, Withdrawn Disopyramide Vilanterol may increase the QTc-prolonging activities of Disopyramide. Approved Dofetilide Vilanterol may increase the QTc-prolonging activities of Dofetilide. Approved, Investigational Dolasetron Vilanterol may increase the QTc-prolonging activities of Dolasetron. Approved, Investigational 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 Doxazosin Doxazosin may decrease the vasoconstricting activities of Vilanterol. Approved Doxepin The risk or severity of adverse effects can be increased when Doxepin is combined with Vilanterol. Approved, Investigational Doxofylline The risk or severity of adverse effects can be increased when Doxofylline is combined with Vilanterol. Approved, Investigational 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 Duloxetine Duloxetine may increase the tachycardic activities of Vilanterol. Approved 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 Epinephrine Epinephrine may decrease the vasoconstricting activities of Vilanterol. Approved, Vet Approved Epitizide Vilanterol may increase the hypokalemic activities of Epitizide. Experimental Ergoloid mesylate Ergoloid mesylate may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved Ergonovine Ergonovine may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved Ergotamine Ergotamine may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved Erythromycin The metabolism of Vilanterol can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Escitalopram Vilanterol may increase the QTc-prolonging activities of Escitalopram. Approved, Investigational Esmolol Esmolol may decrease the bronchodilatory activities of Vilanterol. Approved Etacrynic acid Vilanterol may increase the hypokalemic activities of Etacrynic acid. Approved, Investigational 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, Investigational Fluoxetine Vilanterol may increase the QTc-prolonging activities of Fluoxetine. Approved, Vet Approved Flupentixol Vilanterol may increase the QTc-prolonging activities of Flupentixol. Approved, Investigational, 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, Investigational Furazolidone The risk or severity of adverse effects can be increased when Furazolidone is combined with Vilanterol. Approved, Investigational, 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, Investigational 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, Investigational Gemifloxacin Vilanterol may increase the QTc-prolonging activities of Gemifloxacin. Approved, Investigational GI-5005 The risk or severity of adverse effects can be increased when Vilanterol is combined with GI-5005. 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 Harmaline The risk or severity of adverse effects can be increased when Harmaline is combined with Vilanterol. Experimental Hepatitis A Vaccine The risk or severity of adverse effects can be increased when Vilanterol is combined with Hepatitis A Vaccine. Approved Hepatitis B Vaccine (Recombinant) The risk or severity of adverse effects can be increased when Vilanterol is combined with Hepatitis B Vaccine (Recombinant). Approved, Withdrawn Human rabies virus immune globulin The risk or severity of adverse effects can be increased when Vilanterol is combined with Human rabies virus immune globulin. 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, Investigational Ibutilide Vilanterol may increase the QTc-prolonging activities of Ibutilide. Approved Idelalisib The metabolism of Vilanterol can be decreased when 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 Indoramin Indoramin may decrease the vasoconstricting activities of Vilanterol. Withdrawn 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 Iprindole The risk or severity of adverse effects can be increased when Iprindole is combined with Vilanterol. Experimental 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 Isavuconazole The serum concentration of Vilanterol can be increased when it is combined with Isavuconazole. Approved, Investigational 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, Investigational 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 Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Vilanterol is combined with Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated). Approved Ketoconazole The metabolism of Vilanterol can be decreased when combined with Ketoconazole. Approved, Investigational Labetalol Labetalol may decrease the vasoconstricting activities of Vilanterol. Approved 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, Investigational Leuprolide Vilanterol may increase the QTc-prolonging activities of Leuprolide. Approved, Investigational Levofloxacin Vilanterol may increase the QTc-prolonging activities of Levofloxacin. Approved, Investigational Levomilnacipran Levomilnacipran may increase the tachycardic activities of Vilanterol. Approved, Investigational Lisdexamfetamine Lisdexamfetamine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Lofepramine The risk or severity of adverse effects can be increased when Lofepramine is combined with Vilanterol. Experimental Lopinavir The metabolism of Vilanterol can be decreased when combined with Lopinavir. Approved Lorpiprazole The serum concentration of Vilanterol can be increased when it is combined with Lorpiprazole. Approved Lovastatin The metabolism of Vilanterol can be decreased when combined with Lovastatin. Approved, Investigational Loxapine The therapeutic efficacy of Vilanterol can be decreased when used in combination 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 Melitracen The risk or severity of adverse effects can be increased when Melitracen is combined with Vilanterol. Experimental, Investigational Mepindolol Mepindolol may decrease the bronchodilatory activities of Vilanterol. Experimental Methadone Vilanterol may increase the QTc-prolonging activities of Methadone. Approved Methotrimeprazine Methotrimeprazine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational 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. Approved, Investigational Methylergometrine Methylergometrine may increase the hypertensive and vasoconstricting activities of Vilanterol. Approved Metolazone Vilanterol may increase the hypokalemic activities of Metolazone. Approved Metoprolol Metoprolol may decrease the bronchodilatory activities of Vilanterol. Approved, Investigational Mifepristone The serum concentration of Vilanterol can be increased when it is combined with Mifepristone. Approved, Investigational Milnacipran Milnacipran may increase the tachycardic activities of Vilanterol. Approved, Investigational Minaprine The risk or severity of adverse effects can be increased when Minaprine 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, Investigational Moxifloxacin Vilanterol may increase the QTc-prolonging activities of Moxifloxacin. Approved, Investigational Nadolol Nadolol may decrease the bronchodilatory activities of Vilanterol. 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, Investigational 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 Nicardipine Nicardipine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Nicergoline Nicergoline may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Niguldipine Niguldipine may decrease the vasoconstricting activities of Vilanterol. Experimental 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 Ocrelizumab Ocrelizumab may increase the immunosuppressive activities of Vilanterol. Approved, Investigational 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 Olanzapine Olanzapine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational 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, Investigational 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, Investigational Pentobarbital The metabolism of Vilanterol can be increased when combined with Pentobarbital. Approved, Investigational, 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, Investigational Phenoxybenzamine Phenoxybenzamine may decrease the vasoconstricting activities of Vilanterol. Approved Phenoxypropazine The risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Vilanterol. Withdrawn Phentolamine Phentolamine may decrease the vasoconstricting activities of Vilanterol. Approved 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, Investigational Piretanide Vilanterol may increase the hypokalemic activities of Piretanide. Approved Pirlindole The risk or severity of adverse effects can be increased when Pirlindole is combined with Vilanterol. Approved Pitolisant The serum concentration of Vilanterol can be decreased when it is combined with Pitolisant. Approved, Investigational Pivhydrazine The risk or severity of adverse effects can be increased when Pivhydrazine is combined with Vilanterol. Withdrawn Pizotifen Pizotifen may decrease the vasoconstricting activities of Vilanterol. Approved 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 Prazosin Prazosin may decrease the vasoconstricting activities of Vilanterol. 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 Procaine The risk or severity of adverse effects can be increased when Procaine is combined with Vilanterol. Approved, Investigational, Vet Approved Procarbazine The risk or severity of adverse effects can be increased when Procarbazine is combined with Vilanterol. Approved, Investigational Promazine Vilanterol may increase the QTc-prolonging activities of Promazine. Approved, Vet Approved Propafenone Vilanterol may increase the QTc-prolonging activities of Propafenone. Approved Propericiazine Propericiazine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Propiomazine Propiomazine may decrease the vasoconstricting activities of Vilanterol. Approved Propiverine Propiverine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational 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, Investigational Quinine Vilanterol may increase the QTc-prolonging activities of Quinine. Approved Rabies virus inactivated antigen, A The risk or severity of adverse effects can be increased when Vilanterol is combined with Rabies virus inactivated antigen, A. Approved, Investigational Rabies virus inactivated antigen, A The therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Vilanterol. Approved, Investigational Racepinephrine Racepinephrine may decrease the vasoconstricting activities of Vilanterol. 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, Investigational 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, Investigational Rindopepimut The risk or severity of adverse effects can be increased when Vilanterol is combined with Rindopepimut. Investigational Risperidone Risperidone may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Roflumilast Roflumilast may increase the immunosuppressive activities of Vilanterol. Approved Rotavirus Vaccine The risk or severity of adverse effects can be increased when Vilanterol is combined with Rotavirus Vaccine. Approved Rubella virus vaccine The risk or severity of adverse effects can be increased when Vilanterol is combined with Rubella virus vaccine. Approved, Investigational Rucaparib The metabolism of Vilanterol can be decreased when combined with Rucaparib. Approved, Investigational Safrazine The risk or severity of adverse effects can be increased when Safrazine is combined with Vilanterol. Withdrawn Salmonella typhi ty2 vi polysaccharide antigen The risk or severity of adverse effects can be increased when Vilanterol is combined with Salmonella typhi ty2 vi polysaccharide antigen. Approved Salmonella typhi ty21a live antigen The risk or severity of adverse effects can be increased when Vilanterol is combined with Salmonella typhi ty21a live antigen. Approved Saquinavir The metabolism of Vilanterol can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Vilanterol can be decreased when used in combination with Sarilumab. 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 Silodosin Silodosin may decrease the vasoconstricting activities of Vilanterol. Approved Siltuximab The serum concentration of Vilanterol can be decreased when it is combined with Siltuximab. Approved, Investigational 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, Investigational Sotalol Sotalol may decrease the bronchodilatory activities of Vilanterol. Approved Spironolactone Spironolactone may decrease the vasoconstricting 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. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Vilanterol can be increased when it is combined with Stiripentol. Approved Sulfisoxazole The metabolism of Vilanterol can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Tacrolimus Tacrolimus may increase the immunosuppressive activities of Vilanterol. Approved, Investigational Tamsulosin Tamsulosin may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Tecemotide The risk or severity of adverse effects can be increased when Vilanterol is combined with Tecemotide. Investigational Telaprevir The metabolism of Vilanterol can be decreased when combined with Telaprevir. Approved, 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 Terazosin Terazosin may decrease the vasoconstricting activities of Vilanterol. Approved Tertatolol Tertatolol may decrease the bronchodilatory activities of Vilanterol. Experimental Tetrabenazine Vilanterol may increase the QTc-prolonging activities of Tetrabenazine. Approved, Investigational TG4010 The risk or severity of adverse effects can be increased when Vilanterol is combined with TG4010. Investigational Thioproperazine Thioproperazine may decrease the vasoconstricting activities of Vilanterol. Approved Thioridazine Vilanterol may increase the QTc-prolonging activities of Thioridazine. Approved, Withdrawn Tianeptine The risk or severity of adverse effects can be increased when Tianeptine is combined with Vilanterol. Approved, Investigational 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 Tolazoline Tolazoline may decrease the vasoconstricting activities of Vilanterol. Approved, Vet Approved 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 Tranylcypromine The risk or severity of adverse effects can be increased when Tranylcypromine is combined with Vilanterol. Approved, Investigational Trastuzumab Trastuzumab may increase the neutropenic activities of Vilanterol. Approved, Investigational Trazodone Trazodone may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Trichlormethiazide Vilanterol may increase the hypokalemic activities of Trichlormethiazide. Approved, Vet Approved Trifluoperazine Trifluoperazine may decrease the vasoconstricting activities of Vilanterol. Approved, Investigational Trimazosin Trimazosin may decrease the vasoconstricting activities of Vilanterol. Experimental Trimipramine The risk or severity of adverse effects can be increased when Trimipramine is combined with Vilanterol. Approved Typhoid Vaccine The risk or severity of adverse effects can be increased when Vilanterol is combined with Typhoid Vaccine. Approved Urapidil Urapidil may decrease the vasoconstricting activities of Vilanterol. Investigational Vandetanib Vilanterol may increase the QTc-prolonging activities of Vandetanib. Approved Varicella Zoster Vaccine (Live/Attenuated) The risk or severity of adverse effects can be increased when Vilanterol is combined with Varicella Zoster Vaccine (Live/Attenuated). Approved Vemurafenib The risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Vilanterol. Approved Venlafaxine Venlafaxine may increase the tachycardic activities of Vilanterol. 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 Yellow Fever Vaccine The risk or severity of adverse effects can be increased when Vilanterol is combined with Yellow Fever Vaccine. 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
- 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
- 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 furoate
- 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) 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 US9750726 No 2010-11-29 2030-11-29 US US9750762 No 2010-11-29 2030-11-29 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 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
- 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 July 02, 2018 20:41