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Identification
- Summary
Vilanterol is a long-acting beta2-adrenergic agonist used in combination with other bronchodilators for the management of chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema.
- Brand Names
- Anoro, Anoro Ellipta, Breo Ellipta, Trelegy Ellipta
- Generic Name
- Vilanterol
- DrugBank Accession Number
- DB09082
- Background
Vilanterol is a selective long-acting β2-adrenergic agonist (LABA) with inherent 24-hour activity for the once-daily treatment of COPD and asthma.1 This is in response to the need for longer-acting β2-adrenergic agonists to overcome poor patient compliance (due to the frequency of dosing regimens or complexities of drug administration).3 Vilanterol was designed based on the salmeterol molecular scaffold, particularly as a antedrug analog of salmeterol modification by modifying the salmeterol molecule to create homochiral compounds with the (R)-configuration.3 Vilanterol is 1000 and 400 fold more selective for β2 than β1 and β3 adrenoceptors, respectively, with a faster onset of action than salmeterol.4 Additionally, vilanterol demonstrated a significantly longer duration of action than salmeterol, with the bronchodilator effect still apparent at 22h.4 Vilanterol's 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 the relaxation of bronchial smooth muscle and inhibition of the release of hypersensitivity mediators from mast cells in the lungs.2,3
Vilanterol is approved for use in several combination products such as with fluticasone furoate under the tradename BREO ELLIPTA, with [umeclidinium bromide] as ANORO ELLIPTA, and with both fluticasone furoate and [umeclidinium bromide] under the trade name TRELEGY ELLIPTA.8,7,6 BREO ELLIPTA is the first vilanterol-containing product to be approved by the FDA in May 2013, followed by ANORO ELLIPTA in December 2013 and TRELEGY ELLIPTA in September 2020.10,11,12 Although all 3 products are approved for the maintenance treatment of chronic obstructive pulmonary disease (COPD), only TRELEGY ELLIPTA and BREO ELLIPTA are approved for maintenance treatments of asthma in patients aged 18 years and older and 5 years and older respectively.8,7,6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Vilanterol (DB09082)
- Weight
- Average: 486.43
Monoisotopic: 485.1735786 - Chemical Formula
- C24H33Cl2NO5
- Synonyms
- Vilantérol
- Vilanterol
- Vilanterolum
- External IDs
- GW 642444M
- GW 642444X
- GW-642444
- GW-642444M
- GW-642444X
- GW642444
- GW642444M
- GW642444X
Pharmacology
- Indication
Vilanterol is approved for use in several combination products such as with fluticasone furoate under the tradename Breo Ellipta,5 in combination with umeclidinium bromide as Anoro Ellipta,7 and in combination with both fluticasone furoate and umeclidinium under the tradename Trelegy Ellipta.6
Approved by the FDA in 2013, the 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, as well as the once-daily maintenance treatment of asthma in patients aged 18 or older with reversible obstructive airways disease. Anoro Ellipta is indicated for the maintenance treatment of patients with COPD7, and Trelegy Ellipta is indicated for the maintenance treatment of patients with COPD as well as the maintenance treatment of asthma in patients aged 18 years and older.6
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Asthma Combination Product in combination with: Fluticasone furoate (DB08906) •••••••••••• •••••• Used in combination to manage Asthma Combination Product in combination with: Fluticasone furoate (DB08906), Umeclidinium (DB09076) •••••••••••• •••••• Used in combination to manage Chronic obstructive pulmonary disease Combination Product in combination with: Umeclidinium (DB09076) •••••••••••• •••••• Used in combination to manage Chronic obstructive pulmonary disease Combination Product in combination with: Fluticasone furoate (DB08906) •••••••••••• •••••• Used in combination to manage Chronic obstructive pulmonary disease (copd) Combination Product in combination with: Umeclidinium (DB09076), Fluticasone furoate (DB08906) •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Vilanterol is a selective long-acting beta2-adrenergic agonist. Its pharmacological effect is attributable to stimulation of intracellular adenylyl cyclase which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cAMP). Increases in cyclic AMP are associated with relaxation of bronchial smooth muscle and inhibition of release of hypersensitivity mediators from mast cells in the lungs.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - Absorption
Vilanterol plasma levels may not predict therapeutic effects. Following inhaled administration of vilanterol in healthy subjects, Cmax occurred at 5 to 15 minutes. Vilanterol is mostly absorbed from the lung after inhaled doses with negligible contribution from oral absorption.7 Following repeat dosing of inhaled vilanterol, the steady state was achieved within 14 days with up to 1.7-fold accumulation.6
The absolute bioavailability of vilanterol when administered by inhalation was 27.3%, primarily due to absorption of the inhaled portion of the dose delivered to the lung. Oral bioavailability from the swallowed portion of the dose of vilanterol is low (<2%) due to extensive first-pass metabolism. Systemic exposure (AUC) in patients with COPD was 24% higher than observed in healthy subjects. Systemic exposure (AUC) in patients with asthma was 21% lower than observed in healthy subjects.8
- Volume of distribution
Following intravenous administration to healthy subjects, the mean volume of distribution at steady-state was 165 L.7
- Protein binding
In vitro plasma protein binding in human plasma was on average 94%.7
- Metabolism
Vilanterol is principally metabolized by cytochrome p450 3A4 (CYP3A4) to a range of metabolites with significantly reduced beta1- and beta2-agonist activity. The major route of metabolism was via O-dealkylation, with up to 78% of the recovered dose eliminated as O-dealkylated metabolites while N-Dealkylation and C-dealkylation were minor pathways, representing 5% of the recovered dose.
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- Route of elimination
Following oral administration of radiolabeled vilanterol, mass balance showed 70% of the radiolabel in the urine and 30% in the feces.7
- Half-life
The effective half-life for vilanterol, as determined from inhalation administration of multiple doses, is 11 hours.7 The plasma elimination half-life, as determined from inhalation administration of multiple doses of vilanterol 25 mcg, is 21.3 hours in patients with COPD and 16.0 hours in patients with asthma.8 For a single dose inhaled administration, the plasma elimination phase half-life averaged 2.5 hour.9
- Clearance
Following intravenous administration, the pharmacokinetics of vilanterol showed a high plasma clearance of 108 L/hour.9
- Adverse Effects
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In separate embryofetal developmental studies, pregnant rats and rabbits received vilanterol during the period of organogenesis at doses up to approximately 13,000 and 450 times, respectively, the maximum recommended human daily inhaled dose (MRHDID) (on an mcg/m2 basis at maternal inhalation doses up to 33,700 mcg/kg/day in rats and on an AUC basis at maternal inhaled doses up to 5,740 mcg/kg/day in rabbits). No evidence of structural abnormalities was observed at any dose in rats or in rabbits up to approximately 70 times the MRHDID (on an AUC basis at maternal doses up to 591 mcg/kg/day in rabbits). However, fetal skeletal variations were observed in rabbits at approximately 450 times the MRHDID (on an AUC basis at maternal inhaled or subcutaneous doses of 5,740 or 300 mcg/kg/day, respectively). The skeletal variations included decreased or absent ossification in the cervical vertebral centrum and metacarpals.7
In a perinatal and postnatal developmental study in rats, dams received vilanterol during late gestation and the lactation periods at doses up to approximately 3,900 times the MRHDID (on an mcg/m2 basis at maternal oral doses up to 10,000 mcg/kg/day). No evidence of effects on offspring development was observed.7
The expected signs and symptoms with overdosage of vilanterol are those of excessive beta-adrenergic stimulation and/or occurrence or exaggeration of any of the signs and symptoms of beta-adrenergic stimulation (e.g., seizures, angina, hypertension or hypotension, tachycardia with rates up to 200 beats/min, arrhythmias, nervousness, headache, tremor, muscle cramps, dry mouth, palpitation, nausea, dizziness, fatigue, malaise, insomnia, hyperglycemia, hypokalemia, metabolic acidosis). As with all inhaled sympathomimetic medicines, cardiac arrest, and even death may be associated with an overdose of vilanterol.7
In a 2-year carcinogenicity study in mice, vilanterol caused a statistically significant increase in ovarian tubulostromal adenomas in females at an inhaled dose of 29,500 mcg/kg/day (approximately 7,800 times the MRHDID for adults on an AUC basis). No increase in tumors was seen at an inhaled dose of 615 mcg/kg/day (approximately 210 times the MRHDID for adults on an AUC basis).7
In a 2-year carcinogenicity study in rats, vilanterol caused statistically significant increases in mesovarian leiomyomas in females and a shortening of the latency of pituitary tumors at inhaled doses greater than or equal to 84.4 mcg/kg/day (greater than or equal to approximately 20 times the MRHDID for adults on an AUC basis). No tumors were seen at an inhaled dose of 10.5 mcg/kg/day (approximately equal to the MRHDID for adults on an AUC basis).7
These tumor findings in rodents are similar to those reported previously for other beta-adrenergic agonist drugs. The relevance of these findings to human use is unknown.7
Vilanterol tested negative in the following genotoxicity assays: the in vitro Ames assay, in vivo rat bone marrow micronucleus assay, in vivo rat unscheduled DNA synthesis (UDS) assay, and in vitro Syrian hamster embryo (SHE) cell assay. Vilanterol tested equivocal in the in vitro mouse lymphoma assay.7
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Vilanterol which could result in a higher serum level. Abametapir The serum concentration of Vilanterol can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Vilanterol. Acebutolol The therapeutic efficacy of Vilanterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Vilanterol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Region Image Anoro Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxosmithkline Inc 2016-09-08 Not applicable EU 
Anoro Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxosmithkline Inc 2016-09-08 Not applicable EU Anoro Vilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms) Powder, metered Respiratory (inhalation) Glaxosmithkline Inc 2016-09-08 Not applicable EU Anoro Ellipta Vilanterol trifenatate (25 mcg / act) + Umeclidinium bromide (62.5 mcg / act) Powder Respiratory (inhalation) Glaxosmithkline Inc 2014-03-14 Not applicable Canada 
Anoro Ellipta Vilanterol trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1) Powder Respiratory (inhalation) Glaxosmithkline Inc 2014-01-31 Not applicable US 
Categories
- ATC Codes
- R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoate
- R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03AK — Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Benzene Derivatives
- Benzyl Compounds
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs for Obstructive Airway Diseases
- Drugs that are Mainly Renally Excreted
- Hydrocarbons, Chlorinated
- Hydrocarbons, Halogenated
- Immunosuppressive Agents
- Long-acting beta-adrenoceptor agonists
- P-glycoprotein substrates
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzylethers
- Direct Parent
- Benzylethers
- Alternative Parents
- Dichlorobenzenes / Benzyl alcohols / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Dialkyl ethers / Primary alcohols show 4 more
- Substituents
- 1,2-aminoalcohol / 1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide show 19 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, benzyl alcohols, secondary amino compound, ether, dichlorobenzene (CHEBI:75037)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 028LZY775B
- CAS number
- 503068-34-6
- InChI Key
- DAFYYTQWSAWIGS-DEOSSOPVSA-N
- InChI
- InChI=1S/C24H33Cl2NO5/c25-21-6-5-7-22(26)20(21)17-32-13-12-31-11-4-2-1-3-10-27-15-24(30)18-8-9-23(29)19(14-18)16-28/h5-9,14,24,27-30H,1-4,10-13,15-17H2/t24-/m0/s1
- IUPAC Name
- 4-[(1R)-2-[(6-{2-[(2,6-dichlorophenyl)methoxy]ethoxy}hexyl)amino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol
- SMILES
- OCC1=C(O)C=CC(=C1)[C@@H](O)CNCCCCCCOCCOCC1=C(Cl)C=CC=C1Cl
References
- General References
- Harrell AW, Siederer SK, Bal J, Patel NH, Young GC, Felgate CC, Pearce SJ, Roberts AD, Beaumont C, Emmons AJ, Pereira AI, Kempsford RD: Metabolism and disposition of vilanterol, a long-acting beta(2)-adrenoceptor agonist for inhalation use in humans. Drug Metab Dispos. 2013 Jan;41(1):89-100. doi: 10.1124/dmd.112.048603. Epub 2012 Oct 4. [Article]
- Spyratos D, Sichletidis L: Umeclidinium bromide/vilanterol combination in the treatment of chronic obstructive pulmonary disease: a review. Ther Clin Risk Manag. 2015 Mar 25;11:481-7. doi: 10.2147/TCRM.S67491. eCollection 2015. [Article]
- Malerba M, Radaeli A, Montuschi P, Morjaria JB: Vilanterol trifenatate for the treatment of COPD. Expert Rev Respir Med. 2016 Jul;10(7):719-31. doi: 10.1080/17476348.2016.1184976. Epub 2016 May 25. [Article]
- Kempsford R, Norris V, Siederer S: Vilanterol trifenatate, a novel inhaled long-acting beta2 adrenoceptor agonist, is well tolerated in healthy subjects and demonstrates prolonged bronchodilation in subjects with asthma and COPD. Pulm Pharmacol Ther. 2013 Apr;26(2):256-64. doi: 10.1016/j.pupt.2012.12.001. Epub 2012 Dec 8. [Article]
- FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation [Link]
- FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation (December 2022) [Link]
- FDA Approved Drug Products: ANORO ELLIPTA (umeclidinium and vilanterol inhalation powder) for oral inhalation use [Link]
- FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation (May 2023) [Link]
- Health Canada Approved Drug Proucts: BREO ELLIPTA (fluticasone furoate/vilantero) dry powder for oral inhalation [Link]
- FDA approves BREO® ELLIPTA® for the treatment of adults with asthma in the US [Link]
- FDA approves Anoro Ellipta to treat chronic obstructive pulmonary disease [Link]
- FDA approves Trelegy Ellipta as the first once-daily single inhaler triple therapy for the treatment of both asthma and COPD in the US [Link]
- External Links
- KEGG Drug
- D09696
- PubChem Compound
- 10184665
- PubChem Substance
- 347827825
- ChemSpider
- 8360167
- BindingDB
- 50416060
- 1424884
- ChEBI
- 75037
- ChEMBL
- CHEMBL1198857
- ZINC
- ZINC000003991624
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vilanterol
- FDA label
- Download (12.2 MB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Chronic Obstructive Pulmonary Disease (COPD) 4 somestatus stop reason just information to hide Not Available Recruiting Basic Science Exercise Performance 2 somestatus stop reason just information to hide 4 Completed Basic Science Chronic Obstructive Pulmonary Disease (COPD) 2 somestatus stop reason just information to hide 4 Completed Treatment Asthma 2 somestatus stop reason just information to hide 4 Completed Treatment Asthma in Children 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, metered Respiratory (inhalation) 62.5 mcg Powder Oral; Respiratory (inhalation) 55 mcg Powder Respiratory (inhalation) Aerosol, powder Respiratory (inhalation) Powder, metered Respiratory (inhalation) Powder Oral; Respiratory (inhalation) Powder Buccal Powder Respiratory (inhalation) 25 mcg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5873360 Yes 1999-02-23 2016-08-23 US US7101866 No 2006-09-05 2021-08-03 US US7439393 Yes 2008-10-21 2025-11-21 US US6759398 No 2004-07-06 2021-08-03 US USRE44874 No 2014-04-29 2023-03-23 US US6537983 No 2003-03-25 2021-08-03 US US8511304 Yes 2013-08-20 2027-12-14 US US7629335 No 2009-12-08 2021-08-03 US US8161968 Yes 2012-04-24 2028-08-05 US US8746242 Yes 2014-06-10 2031-04-11 US US8113199 Yes 2012-02-14 2028-04-23 US US7776895 No 2010-08-17 2022-09-11 US US8534281 Yes 2013-09-17 2030-09-08 US US6878698 No 2005-04-12 2021-08-03 US US8309572 No 2012-11-13 2025-04-27 US US8183257 No 2012-05-22 2025-07-27 US US7488827 No 2009-02-10 2025-04-27 US US7498440 No 2009-03-03 2025-04-27 US US9333310 Yes 2016-05-10 2028-04-02 US US9750726 No 2017-09-05 2030-11-29 US US9750762 No 2017-09-05 2030-11-29 US US11116721 Yes 2021-09-14 2029-08-26 US US11090294 No 2021-08-17 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 53.67 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uy0-0001900000-1ada0b83dd1e561a2b46 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0770900000-716b2a17d135a23fb5aa Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pvr-0315900000-6479a41d7d46a8b832e7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001r-6842900000-552fad2cfc3e3b67c7af Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-0912100000-03822d0379f975b30b9b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9821600000-af9563f9f3044b398c85 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 210.49532 predictedDeepCCS 1.0 (2019) [M+H]+ 212.97693 predictedDeepCCS 1.0 (2019) [M+Na]+ 219.68214 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- FDA Approved Drug Products: ANORO ELLIPTA (umeclidinium and vilanterol inhalation powder) for oral inhalation use [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- FDA Approved Drug Products: ANORO ELLIPTA (umeclidinium and vilanterol inhalation powder) for oral inhalation use [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- FDA Approved Drug Products: ANORO ELLIPTA (umeclidinium and vilanterol inhalation powder) for oral inhalation use [Link]
Drug created at August 31, 2015 17:12 / Updated at October 30, 2024 23:03