Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H33Cl2NO5 |
Molecular Weight | 486.429 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=C(O)C=CC(=C1)[C@@H](O)CNCCCCCCOCCOCC2=C(Cl)C=CC=C2Cl
InChI
InChIKey=DAFYYTQWSAWIGS-DEOSSOPVSA-N
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
Molecular Formula | C24H33Cl2NO5 |
Molecular Weight | 486.429 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB09082
Curator's Comment: description was created based on several sources, including
http://www.drugbank.ca/drugs/DB09082
Vilanterol (INN, USAN) is an ultra-long-acting β2 adrenoreceptor agonist (ultra-LABA), which was approved in May 2013 in combination with fluticasone furoate for sale as Breo Ellipta by GlaxoSmithKline for the treatment of chronic obstructive pulmonary disease (COPD). 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 available in following combinations: a) with inhaled corticosteroid fluticasone furoate — fluticasone furoate/vilanterol (trade names Breo Ellipta , Relvar Ellipta; b) with muscarinic antagonist umeclidinium bromide — umeclidinium bromide/vilanterol (trade name Anoro Ellipta).
Originator
Sources: https://us.gsk.com/en-us/media/press-releases/2014/anoro-ellipta-now-available-in-the-us-for-treatment-of-copd/
Curator's Comment: http://www.ncbi.nlm.nih.gov/pubmed/?term=20462258
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P07550 Gene Symbol: ADRB2 |
9.42 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | ANORO ELLIPTA Approved UseANORO ELLIPTA is a combination of umeclidinium, an anticholinergic, and vilanterol, a long-acting beta2-adrenergic agonist (LABA), indicated for the long-term, once-daily, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD). Not indicated for relief of acute bronchospasm or for the treatment of asthma. Launch Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
205 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25816315/ |
25 μg 1 times / day multiple, oral dose: 25 μg route of administration: Oral experiment type: MULTIPLE co-administered: UMECLIDINIUM |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
239 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25816315/ |
25 μg 1 times / day multiple, oral dose: 25 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
495.9 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23284643/ |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
118 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25816315/ |
25 μg 1 times / day multiple, oral dose: 25 μg route of administration: Oral experiment type: MULTIPLE co-administered: UMECLIDINIUM |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
214 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25816315/ |
25 μg 1 times / day multiple, oral dose: 25 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
251.4 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23284643/ |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25816315/ |
25 μg 1 times / day multiple, oral dose: 25 μg route of administration: Oral experiment type: MULTIPLE co-administered: UMECLIDINIUM |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23284643/ |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] VILANTEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 ug 1 times / day multiple, respiratory Highest studied dose Dose: 100 ug, 1 times / day Route: respiratory Route: multiple Dose: 100 ug, 1 times / day Sources: |
healthy, 29.1 years (range: 21-53 years) n = 9 Health Status: healthy Age Group: 29.1 years (range: 21-53 years) Sex: M Population Size: 9 Sources: |
Other AEs: Nasopharyngitis, Constipation... Other AEs: Nasopharyngitis (1 patient) Sources: Constipation (1 patient) Hot flush (1 patient) Muscle twitching (1 patient) |
500 ug multiple, oral Highest studied dose |
healthy, 33.1 years (range: 19–47 years) n = 9 Health Status: healthy Age Group: 33.1 years (range: 19–47 years) Sex: M Population Size: 9 Sources: |
|
100 ug multiple, respiratory Highest studied dose Dose: 100 ug Route: respiratory Route: multiple Dose: 100 ug Sources: |
unhealthy, 36.9 years (range: 21-60 years) n = 22 Health Status: unhealthy Condition: asthma Age Group: 36.9 years (range: 21-60 years) Sex: M Population Size: 22 Sources: |
Other AEs: Application site rash... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Constipation | 1 patient | 100 ug 1 times / day multiple, respiratory Highest studied dose Dose: 100 ug, 1 times / day Route: respiratory Route: multiple Dose: 100 ug, 1 times / day Sources: |
healthy, 29.1 years (range: 21-53 years) n = 9 Health Status: healthy Age Group: 29.1 years (range: 21-53 years) Sex: M Population Size: 9 Sources: |
Hot flush | 1 patient | 100 ug 1 times / day multiple, respiratory Highest studied dose Dose: 100 ug, 1 times / day Route: respiratory Route: multiple Dose: 100 ug, 1 times / day Sources: |
healthy, 29.1 years (range: 21-53 years) n = 9 Health Status: healthy Age Group: 29.1 years (range: 21-53 years) Sex: M Population Size: 9 Sources: |
Muscle twitching | 1 patient | 100 ug 1 times / day multiple, respiratory Highest studied dose Dose: 100 ug, 1 times / day Route: respiratory Route: multiple Dose: 100 ug, 1 times / day Sources: |
healthy, 29.1 years (range: 21-53 years) n = 9 Health Status: healthy Age Group: 29.1 years (range: 21-53 years) Sex: M Population Size: 9 Sources: |
Nasopharyngitis | 1 patient | 100 ug 1 times / day multiple, respiratory Highest studied dose Dose: 100 ug, 1 times / day Route: respiratory Route: multiple Dose: 100 ug, 1 times / day Sources: |
healthy, 29.1 years (range: 21-53 years) n = 9 Health Status: healthy Age Group: 29.1 years (range: 21-53 years) Sex: M Population Size: 9 Sources: |
Application site rash | 1 patient | 100 ug multiple, respiratory Highest studied dose Dose: 100 ug Route: respiratory Route: multiple Dose: 100 ug Sources: |
unhealthy, 36.9 years (range: 21-60 years) n = 22 Health Status: unhealthy Condition: asthma Age Group: 36.9 years (range: 21-60 years) Sex: M Population Size: 22 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=108 Page: 108.0 |
no [Inhibition 100 uM] | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=107 Page: 107.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=107 Page: 107.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=107 Page: 107.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=40 Page: 40.0 |
yes [IC50 4 uM] | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=40 Page: 40.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=106 Page: 106.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=106 Page: 106.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=106 Page: 106.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=106 Page: 106.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=106 Page: 106.0 |
minor | |||
yes | unlikely Comment: VI pharmacokinetics was not affected by P-gp inhibition. Drug interaction trials with a specific P-gp inhibitor and fluticasone furoate have not been conducted. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=9 Page: 9.0 |
|||
yes | yes (co-administration study) Comment: Co-administration with strong CYP3A4 and potent P-gp inhibitor ketoconazole, resulted in modest increases in mean FF AUC(0-24) and Cmax (by 36% and 33%, respectively) and mean VI AUC(0-t) and Cmax (by 65% and 22%, respectively) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203975Orig1s000ClinPharmR.pdf#page=9 Page: 9.0 |
Sample Use Guides
ANORO ELLIPTA (umeclidinium/vilanterol 62.5 mcg/25 mcg) should be administered as 1 inhalation once daily by the orally inhaled route only. ANORO ELLIPTA should be used at the same time every day. Do not use ANORO ELLIPTA more than 1 time every 24 hours.
Route of Administration:
Respiratory
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=23131596
Vilanterol (taken at 1nM) caused concentration related bronchodilation of human small airways when precontracted with histamine or carbachol and exhibited a comparable EC50 and efficacy (maximum percentage bronchodilation) within each spasmogen tested. EC50 value was 0.6 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:40:33 GMT 2023
by
admin
on
Fri Dec 15 17:40:33 GMT 2023
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Record UNII |
028LZY775B
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Record Status |
Validated (UNII)
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Record Version |
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EMA ASSESSMENT REPORTS |
LAVENTAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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WHO-ATC |
R03AL08
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NDF-RT |
N0000175779
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WHO-VATC |
QR03AL03
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NCI_THESAURUS |
C48149
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WHO-ATC |
R03AL03
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EMA ASSESSMENT REPORTS |
RELVAR ELLIPTA (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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NCI_THESAURUS |
C319
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WHO-ATC |
R03AK10
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WHO-VATC |
QR03AK10
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7353
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1424884
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100000138094
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Vilanterol
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503068-34-6
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UU-68
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028LZY775B
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DTXSID80198318
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DB09082
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CHEMBL1198857
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9198
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10184665
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C550468
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C152875
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4799
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75037
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Vilanterol
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028LZY775B
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SUB77409
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> AGONIST |
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> SUBSTRATE |
However, because of low oral bioavailability, inhibition of P-gp is unlikely to have an impact on the overall bioavailability of vilanterol.
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL; PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
human beta-2 cAMP LANCE assay (n=7-24), a value is mean pEC50 (-logEC50); Vilanterol's beta-2 activity is 10.4 (pEC50)
IN-VITRO
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
FECAL; PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
human beta-1 cAMP LANCE assay (n=7-24), a value is mean pEC50 (-logEC50); Vilanterol's beta-1 activity is 7.0 (pEC50)
IN-VITRO
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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blood-to-plasma ratio | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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