Vilanterol

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAsthmaCombination Product in combination with: Fluticasone furoate (DB08906)••••••••••••••••••
Used in combination to manageAsthmaCombination Product in combination with: Fluticasone furoate (DB08906), Umeclidinium (DB09076)••••••••••••••••••
Used in combination to manageChronic obstructive pulmonary diseaseCombination Product in combination with: Umeclidinium (DB09076)••••••••••••••••••
Used in combination to manageChronic obstructive pulmonary diseaseCombination Product in combination with: Fluticasone furoate (DB08906)••••••••••••••••••
Used in combination to manageChronic obstructive pulmonary disease (copd)Combination Product in combination with: Umeclidinium (DB09076), Fluticasone furoate (DB08906)••••••••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
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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Toxicity

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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Vilanterol which could result in a higher serum level.
AbametapirThe serum concentration of Vilanterol can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Vilanterol.
AcebutololThe therapeutic efficacy of Vilanterol can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Vilanterol.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Vilanterol trifenatate40AHO2C6DG503070-58-4KLOLZALDXGTNQE-JIDHJSLPSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
AnoroVilanterol trifenatate (22 micrograms) + Umeclidinium bromide (55 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Smith Kline (Ireland) Limited2016-09-08Not applicableEU flag
ANORO ELLIPTAVilanterol (22 µg) + Umeclidinium (55 µg)PowderRespiratory (inhalation)Glaxosmithkline (Ireland) Limited2014-10-03Not applicableItaly flag
Anoro ElliptaVilanterol trifenatate (25 ug/1) + Umeclidinium bromide (62.5 ug/1)PowderRespiratory (inhalation)GlaxoSmithKline LLC2014-01-31Not applicableUS flag

Categories

ATC Codes
R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoateR03AK10 — Vilanterol and fluticasone furoateR03AL03 — Vilanterol and umeclidinium bromide
Drug Categories
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
  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. [Article]
  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. [Article]
  3. 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]
  4. 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]
  5. FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation [Link]
  6. FDA Approved Drug Products: Trelegy Ellipta (fluticasone furoate, umeclidinium, and vilanterol) powder for inhalation (December 2022) [Link]
  7. FDA Approved Drug Products: ANORO ELLIPTA (umeclidinium and vilanterol inhalation powder) for oral inhalation use [Link]
  8. FDA Approved Drug Products: Breo Ellipta (fluticasone furoate/vilanterol) powder for inhalation (May 2023) [Link]
  9. Health Canada Approved Drug Proucts: BREO ELLIPTA (fluticasone furoate/vilantero) dry powder for oral inhalation [Link]
  10. FDA approves BREO® ELLIPTA® for the treatment of adults with asthma in the US [Link]
  11. FDA approves Anoro Ellipta to treat chronic obstructive pulmonary disease [Link]
  12. 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]
KEGG Drug
D09696
PubChem Compound
10184665
PubChem Substance
347827825
ChemSpider
8360167
BindingDB
50416060
RxNav
1424884
ChEBI
75037
ChEMBL
CHEMBL1198857
ZINC
ZINC000003991624
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vilanterol
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
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)2somestatusstop reasonjust information to hide
4CompletedTreatmentAsthma2somestatusstop reasonjust information to hide
4CompletedTreatmentAsthma in Children1somestatusstop reasonjust information to hide
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)4somestatusstop reasonjust information to hide
4Not Yet RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder, meteredRespiratory (inhalation)62.5 mcg
PowderOral; Respiratory (inhalation)55 mcg
PowderRespiratory (inhalation)
Aerosol, powderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)
PowderOral; Respiratory (inhalation)
PowderBuccal
PowderRespiratory (inhalation)25 mcg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5873360Yes1999-02-232016-08-23US flag
US7101866No2006-09-052021-08-03US flag
US7439393Yes2008-10-212025-11-21US flag
US6759398No2004-07-062021-08-03US flag
USRE44874No2014-04-292023-03-23US flag
US6537983No2003-03-252021-08-03US flag
US8511304Yes2013-08-202027-12-14US flag
US7629335No2009-12-082021-08-03US flag
US8161968Yes2012-04-242028-08-05US flag
US8746242Yes2014-06-102031-04-11US flag
US8113199Yes2012-02-142028-04-23US flag
US7776895No2010-08-172022-09-11US flag
US8534281Yes2013-09-172030-09-08US flag
US6878698No2005-04-122021-08-03US flag
US8309572No2012-11-132025-04-27US flag
US8183257No2012-05-222025-07-27US flag
US7488827No2009-02-102025-04-27US flag
US7498440No2009-03-032025-04-27US flag
US9333310Yes2016-05-102028-04-02US flag
US9750726No2017-09-052030-11-29US flag
US9750762No2017-09-052030-11-29US flag
US11116721Yes2021-09-142029-08-26US flag
US11090294No2021-08-172030-11-29US flag

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
Polarizability53.67 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/MSsplash10-0uy0-0001900000-1ada0b83dd1e561a2b46
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0770900000-716b2a17d135a23fb5aa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pvr-0315900000-6479a41d7d46a8b832e7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001r-6842900000-552fad2cfc3e3b67c7af
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0912100000-03822d0379f975b30b9b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9821600000-af9563f9f3044b398c85
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-210.49532
predicted
DeepCCS 1.0 (2019)
[M+H]+212.97693
predicted
DeepCCS 1.0 (2019)
[M+Na]+219.68214
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. 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
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
References
  1. 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
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. 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 May 03, 2024 10:14