vilanterol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
bronchodilators, phenethylamine derivatives 4799 503068-34-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • GW642444X
  • vilanterol
  • Breo Ellipta
  • vilanterol trifenatate
  • GW642444M
Vilanterol is a long-acting beta2-adrenergic agonist. The clinical relevance of this in vitro finding is unknown. Although beta2-receptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-receptors are the predominant receptors in the heart, there are also beta2-receptors in the human heart comprising 10% to 50% of the total beta-adrenergic receptors. The precise function of these receptors has not been established, but they raise the possibility that even highly selective beta2-agonists may have cardiac effects. The pharmacologic effects of beta2-adrenergic agonist drugs, including vilanterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
  • Molecular weight: 486.43
  • Formula: C24H33Cl2NO5
  • CLOGP: 3.19
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 4
  • TPSA: 91.18
  • ALOGS: -5.61
  • ROTB: 16

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 2.38 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 25.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.06 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 10, 2013 FDA GLAXO GRP LTD

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Asthma 805.05 14.66 495 19482 91047 46575038
Wheezing 343.78 14.66 238 19739 53148 46612937
Obstructive airways disorder 342.50 14.66 149 19828 13263 46652822
Chronic obstructive pulmonary disease 304.80 14.66 228 19749 57405 46608680
Dyspnoea 222.57 14.66 598 19379 514950 46151135
Blood count abnormal 196.51 14.66 112 19865 17766 46648319
Therapeutic product effect incomplete 167.19 14.66 186 19791 77967 46588118
Cough 161.51 14.66 324 19653 229925 46436160
Nasal polyps 137.58 14.66 47 19930 2163 46663922
Productive cough 130.14 14.66 133 19844 50582 46615503
Sleep disorder due to a general medical condition 96.25 14.66 41 19936 3458 46662627
Respiratory symptom 87.30 14.66 33 19944 2037 46664048
Dyspnoea exertional 81.54 14.66 104 19873 50185 46615900
Embolism venous 81.17 14.66 33 19944 2474 46663611
Chest discomfort 69.06 14.66 132 19845 90137 46575948
Sputum increased 63.38 14.66 25 19952 1731 46664354
Pneumonia 60.04 14.66 318 19659 376002 46290083
Emphysema 57.29 14.66 40 19937 9014 46657071
Sinusitis fungal 55.93 14.66 19 19958 859 46665226
Asthma-chronic obstructive pulmonary disease overlap syndrome 53.61 14.66 16 19961 473 46665612
Salpingo-oophorectomy unilateral 52.88 14.66 15 19962 369 46665716
Dysphonia 52.35 14.66 73 19904 38341 46627744
Toxicity to various agents 50.62 14.66 14 19963 211752 46454333
Total lung capacity increased 50.29 14.66 17 19960 757 46665328
Chronic sinusitis 48.58 14.66 29 19948 5004 46661081
Sleep apnoea syndrome 47.66 14.66 53 19924 22148 46643937
Gastrooesophageal reflux disease 47.62 14.66 101 19876 74243 46591842
Antinuclear antibody negative 45.24 14.66 12 19965 228 46665857
Sputum discoloured 43.12 14.66 39 19938 12739 46653346
Rheumatoid arthritis 41.20 14.66 26 19951 240189 46425896
Herpes simplex reactivation 40.42 14.66 12 19965 348 46665737
Idiopathic intracranial hypertension 39.58 14.66 20 19957 2489 46663596
Coombs positive haemolytic anaemia 39.48 14.66 12 19965 378 46665707
Subclavian vein thrombosis 39.07 14.66 18 19959 1828 46664257
Small cell carcinoma 38.80 14.66 10 19967 169 46665916
Bronchitis 38.42 14.66 116 19861 105863 46560222
Female genital tract fistula 37.48 14.66 21 19956 3218 46662867
Nasal congestion 36.32 14.66 70 19907 48043 46618042
Anosmia 36.19 14.66 22 19955 3922 46662163
Forced expiratory volume decreased 33.35 14.66 23 19954 5081 46661004
Diastolic dysfunction 32.59 14.66 23 19954 5269 46660816
Death 31.95 14.66 249 19728 335299 46330786
Reversible airways obstruction 31.41 14.66 11 19966 545 46665540
Lower respiratory tract infection 30.91 14.66 71 19906 55018 46611067
Rhinitis allergic 29.23 14.66 24 19953 6884 46659201
Oesophageal spasm 28.90 14.66 15 19962 1974 46664111
Bronchiectasis 28.65 14.66 27 19950 9289 46656796
Malaise 28.38 14.66 240 19737 330992 46335093
Bronchial obstruction 28.32 14.66 13 19964 1309 46664776
Oesophageal pain 28.10 14.66 16 19961 2527 46663558
Completed suicide 27.57 14.66 14 19963 145906 46520179
Product dose omission issue 27.14 14.66 143 19834 168377 46497708
Lung neoplasm malignant 26.62 14.66 33 19944 15456 46650629
Lactose intolerance 26.20 14.66 15 19962 2394 46663691
Drug hypersensitivity 26.09 14.66 40 19937 243785 46422300
Gastritis haemorrhagic 25.19 14.66 12 19965 1314 46664771
Eye pruritus 24.84 14.66 28 19949 11870 46654215
Eosinophil count increased 24.58 14.66 23 19954 7843 46658242
Treatment failure 24.49 14.66 5 19972 93082 46573003
Eosinophilic granulomatosis with polyangiitis 24.27 14.66 13 19964 1823 46664262
Upper airway obstruction 24.19 14.66 9 19968 531 46665554
Parotid gland enlargement 24.16 14.66 10 19967 784 46665301
Candida infection 24.15 14.66 38 19939 22202 46643883
Sputum purulent 23.57 14.66 10 19967 834 46665251
Hospitalisation 23.54 14.66 70 19907 63315 46602770
Hyperplastic cholecystopathy 23.25 14.66 6 19971 102 46665983
Febrile neutropenia 23.07 14.66 6 19971 94621 46571464
Staphylococcus test positive 23.06 14.66 16 19961 3568 46662517
Neutropenia 22.53 14.66 17 19960 143187 46522898
Eosinophilia 22.50 14.66 34 19943 19183 46646902
Maternal exposure during pregnancy 22.30 14.66 8 19969 102541 46563544
Antiphospholipid syndrome 22.29 14.66 12 19965 1700 46664385
Haemoptysis 22.12 14.66 40 19937 26149 46639936
Contraindicated product administered 21.65 14.66 4 19973 79943 46586142
Diverticulum 21.09 14.66 25 19952 11181 46654904
Middle insomnia 20.91 14.66 23 19954 9492 46656593
Complex regional pain syndrome 20.19 14.66 12 19965 2054 46664031
Loss of personal independence in daily activities 20.15 14.66 62 19915 57121 46608964
Sarcoidosis 19.92 14.66 17 19960 5142 46660943
Atopy 19.86 14.66 6 19971 185 46665900
Secretion discharge 19.76 14.66 22 19955 9197 46656888
Product dispensing error 19.74 14.66 22 19955 9211 46656874
Eosinophilic oesophagitis 19.27 14.66 6 19971 205 46665880
Respiratory gas exchange disorder 19.22 14.66 7 19970 389 46665696
Tooth injury 19.01 14.66 9 19968 972 46665113
Alopecia 18.99 14.66 25 19952 162389 46503696
Influenza 18.89 14.66 82 19895 89188 46576897
Tricuspid valve incompetence 18.58 14.66 26 19951 13691 46652394
Bronchospasm paradoxical 18.56 14.66 5 19972 101 46665984
Sneezing 18.53 14.66 25 19952 12716 46653369
Hiatus hernia 18.14 14.66 30 19947 18272 46647813
Vascular parkinsonism 18.11 14.66 5 19972 111 46665974
Overdose 17.51 14.66 11 19966 101968 46564117
Ageusia 17.44 14.66 23 19954 11449 46654636
Aspartate aminotransferase increased 17.35 14.66 6 19971 78694 46587391
Nicotine dependence 17.33 14.66 7 19970 516 46665569
Aphonia 17.10 14.66 19 19958 7926 46658159
Disease recurrence 16.61 14.66 29 19948 18442 46647643
Anxiety disorder 16.56 14.66 13 19964 3498 46662587
Bronchospasm 15.91 14.66 26 19951 15681 46650404
Subclavian artery thrombosis 15.84 14.66 5 19972 179 46665906
Catarrh 15.83 14.66 6 19971 373 46665712
Eczema 15.78 14.66 30 19947 20370 46645715
C-reactive protein increased 15.71 14.66 3 19974 58587 46607498
Throat clearing 15.29 14.66 6 19971 410 46665675
Adenoma benign 15.19 14.66 7 19970 711 46665374
Drug ineffective 15.17 14.66 202 19775 677636 45988449
Pleuritic pain 14.95 14.66 16 19961 6400 46659685
Venous pressure jugular increased 14.80 14.66 6 19971 446 46665639
Lung hyperinflation 14.68 14.66 8 19969 1161 46664924

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Asthma 623.91 17.52 302 12082 35872 29904222
Chronic obstructive pulmonary disease 510.41 17.52 286 12098 45840 29894254
Wheezing 325.93 17.52 186 12198 30752 29909342
Obstructive airways disorder 300.33 17.52 120 12264 8939 29931155
Therapeutic product effect incomplete 259.57 17.52 166 12218 33668 29906426
Dyspnoea 204.14 17.52 433 11951 332862 29607232
Blood count abnormal 190.42 17.52 94 12290 11558 29928536
Cough 147.74 17.52 218 12166 125424 29814670
Asthma-chronic obstructive pulmonary disease overlap syndrome 139.60 17.52 36 12348 633 29939461
Sputum discoloured 133.91 17.52 62 12322 6606 29933488
Sinus pain 119.32 17.52 32 12352 659 29939435
Nasal obstruction 115.02 17.52 31 12353 651 29939443
Bronchiectasis 112.69 17.52 51 12333 5153 29934941
Bronchial obstruction 111.45 17.52 36 12348 1440 29938654
Nasal congestion 110.73 17.52 78 12306 18488 29921606
Lung consolidation 93.09 17.52 44 12340 4908 29935186
Pneumonia 90.79 17.52 323 12061 333983 29606111
Chest discomfort 81.19 17.52 97 12287 45383 29894711
Pulmonary function test decreased 80.24 17.52 38 12346 4257 29935837
Throat irritation 78.23 17.52 47 12337 8501 29931593
Pulmonary mass 70.29 17.52 48 12336 10814 29929280
Mycobacterium avium complex infection 69.77 17.52 30 12354 2681 29937413
Emphysema 66.72 17.52 44 12340 9358 29930736
Forced expiratory volume decreased 64.55 17.52 30 12354 3220 29936874
Death 64.12 17.52 304 12080 356979 29583115
Productive cough 63.76 17.52 70 12314 29883 29910211
Appendicolith 63.65 17.52 21 12363 898 29939196
Osteopenia 62.79 17.52 33 12351 4615 29935479
Lymph node calcification 57.39 17.52 14 12370 194 29939900
Foetal malformation 56.39 17.52 13 12371 139 29939955
Vocal cord dysfunction 54.56 17.52 13 12371 162 29939932
Trisomy 18 50.32 17.52 13 12371 230 29939864
Sleep disorder due to a general medical condition 50.02 17.52 20 12364 1487 29938607
Toxicity to various agents 50.00 17.52 7 12377 177176 29762918
Blood immunoglobulin E increased 44.04 17.52 19 12365 1711 29938383
Eosinophil count 42.32 17.52 10 12374 120 29939974
Middle insomnia 40.91 17.52 27 12357 5746 29934348
Failure to anastomose 40.28 17.52 11 12373 243 29939851
Lower respiratory tract infection 39.68 17.52 52 12332 26662 29913432
Respiratory disorder 37.41 17.52 41 12343 17453 29922641
Bronchial disorder 36.96 17.52 14 12370 900 29939194
Forced vital capacity decreased 35.52 17.52 13 12371 759 29939335
Total lung capacity abnormal 33.48 17.52 9 12375 187 29939907
Bronchial hyperreactivity 33.29 17.52 14 12370 1184 29938910
Dyspnoea exertional 32.48 17.52 55 12329 35375 29904719
Blood test abnormal 32.42 17.52 23 12361 5502 29934592
Suffocation feeling 31.65 17.52 11 12373 552 29939542
Hospitalisation 30.76 17.52 61 12323 44258 29895836
Lung hyperinflation 30.73 17.52 12 12372 838 29939256
Lung disorder 30.38 17.52 50 12334 31419 29908675
Secretion discharge 30.06 17.52 19 12365 3756 29936338
Bronchial wall thickening 29.99 17.52 10 12374 442 29939652
Nasal polyps 28.23 17.52 13 12371 1366 29938728
Appendicitis 28.05 17.52 22 12362 6122 29933972
Perfume sensitivity 27.93 17.52 7 12377 109 29939985
Rhinorrhoea 27.16 17.52 38 12346 20716 29919378
Rhinitis 26.80 17.52 19 12365 4540 29935554
Loss of personal independence in daily activities 24.64 17.52 37 12347 21498 29918596
Gastrooesophageal reflux disease 24.34 17.52 46 12338 32209 29907885
Nasal oedema 24.32 17.52 8 12376 339 29939755
Vital capacity decreased 23.10 17.52 8 12376 397 29939697
Eosinophil count increased 22.35 17.52 21 12363 7452 29932642
Panic reaction 21.80 17.52 11 12373 1412 29938682
Sputum increased 21.76 17.52 12 12372 1845 29938249
Drug abuse 21.42 17.52 4 12380 82068 29858026
Choking 21.06 17.52 17 12367 4929 29935165
Neutropenia 20.53 17.52 14 12370 128526 29811568
Pancytopenia 20.45 17.52 5 12379 85047 29855047
Lung opacity 20.31 17.52 9 12375 864 29939230
Meralgia paraesthetica 20.25 17.52 6 12378 179 29939915
Oxygen consumption increased 19.86 17.52 10 12374 1278 29938816
Bronchitis 19.35 17.52 47 12337 39078 29901016
Breath sounds abnormal 19.00 17.52 16 12368 4919 29935175
Nasal inflammation 18.74 17.52 6 12378 233 29939861
Dermatitis atopic 18.61 17.52 9 12375 1055 29939039
Oropharyngeal pain 18.31 17.52 38 12346 28458 29911636
Nasal disorder 17.79 17.52 9 12375 1162 29938932
Apnoeic attack 17.62 17.52 6 12378 283 29939811
Upper-airway cough syndrome 17.58 17.52 12 12372 2698 29937396

Pharmacologic Action:

SourceCodeDescription
ATC R03AK10 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
ATC R03AL03 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
ATC R03AL08 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
FDA MoA N0000009922 Adrenergic beta2-Agonists
FDA EPC N0000175779 beta2-Adrenergic Agonist
CHEBI has role CHEBI:35522 beta-adrenergic receptor agonist
CHEBI has role CHEBI:35523 bronchodilator agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chronic obstructive lung disease indication 13645005 DOID:3083
Chronic bronchitis indication 63480004 DOID:6132
Pulmonary emphysema indication 87433001
Asthma indication 195967001 DOID:2841

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.07 acidic
pKa2 9.28 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.1MG/INH;EQ 0.0625MG BASE/INH;EQ 0.025MG BASE/INH TRELEGY ELLIPTA GLAXOSMITHKLINE N209482 Sept. 18, 2017 RX POWDER INHALATION April 24, 2021 REVISED INDICATION FOR FIXED-DOSE COMBINULLTION OF FLUTICASONE FUROATE, UMECLIDINIUM, AND VILANTEROL TO TREAT AIRFLOW OBSTRUCTION IN CHRONIC OBSTRUCTIVE PULMONULLRY DISEASE (COPD) AND TO REDUCE COPD EXACERBATIONS IN PTS WITH HISTORY OF EXACERBATIONS
EQ 0.0625MG BASE/INH;EQ 0.025MG BASE/INH ANORO ELLIPTA GLAXOSMITHKLINE N203975 Dec. 18, 2013 RX POWDER INHALATION June 9, 2022 ADDITIONULLL INFORMATION ADDED TO THE LABELING BASED ON SAFETY AND EFFICACY DATA FROM THE IMPACT TRIAL
0.1MG/INH;EQ 0.0625MG BASE/INH;EQ 0.025MG BASE/INH TRELEGY ELLIPTA GLAXOSMITHKLINE N209482 Sept. 18, 2017 RX POWDER INHALATION Sept. 9, 2023 MAINTENULLNCE TREATMENT OF ASTHMA IN PATIENTS AGED 18 YEARS AND OLDER
0.2MG/INH;EQ 0.0625MG BASE/INH;EQ 0.025MG BASE/INH TRELEGY ELLIPTA GLAXOSMITHKLINE N209482 Sept. 9, 2020 RX POWDER INHALATION Sept. 9, 2023 NEW STRENGTH

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-2 adrenergic receptor GPCR AGONIST EC50 9.40 WOMBAT-PK CHEMBL
Beta-3 adrenergic receptor GPCR EC50 6.10 WOMBAT-PK
Beta-1 adrenergic receptor GPCR EC50 6.40 WOMBAT-PK

External reference:

IDSource
D09696 KEGG_DRUG
4032565 VUID
N0000188266 NUI
503070-58-4 SECONDARY_CAS_RN
4032565 VANDF
C3644425 UMLSCUI
CHEBI:75040 CHEBI
CHEMBL1084172 ChEMBL_ID
CHEMBL1198857 ChEMBL_ID
CHEMBL1084647 ChEMBL_ID
71306415 PUBCHEM_CID
C550468 MESH_SUPPLEMENTAL_RECORD_UI
9198 INN_ID
028LZY775B UNII
7353 IUPHAR_LIGAND_ID
DB09082 DRUGBANK_ID
1424883 RXNORM
203032 MMSL
29456 MMSL
d08099 MMSL
015022 NDDF
015023 NDDF
702408004 SNOMEDCT_US
702409007 SNOMEDCT_US
720194004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Breo Ellipta HUMAN PRESCRIPTION DRUG LABEL 2 0173-0859 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections
Anoro Ellipta HUMAN PRESCRIPTION DRUG LABEL 2 0173-0869 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections
Breo Ellipta HUMAN PRESCRIPTION DRUG LABEL 2 0173-0882 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections
Trelegy Ellipta HUMAN PRESCRIPTION DRUG LABEL 3 0173-0887 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections
Trelegy Ellipta HUMAN PRESCRIPTION DRUG LABEL 3 0173-0893 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections
Breo Ellipta HUMAN PRESCRIPTION DRUG LABEL 2 70518-2028 POWDER 25 ug RESPIRATORY (INHALATION) NDA 27 sections