Structure via PubChem · Public domain (PubChem)
vilanterol
Sign in to saveAlso known as GW642444X, GW-642444x, vilantérol, 4-{(1R)-2-[(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol
Vilanterol is an ultra-long-acting β2-adrenoceptor agonist 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). The combination is also approved for the treatment of asthma in Canada, Europe, Japan and New Zealand.
Chemical data
- Formula
- C24H33Cl2NO5
- Molecular weight
- 486.4 g/mol
- IUPAC name
- 4-[(1R)-2-[6-[2-[(2,6-dichlorophenyl)methoxy]ethoxy]hexylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol
- SMILES
- C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNC[C@@H](C2=CC(=C(C=C2)O)CO)O)Cl
- InChIKey
- DAFYYTQWSAWIGS-DEOSSOPVSA-N
- XLogP
- 3.8
- Polar surface area
- 91.2 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2013
- Admin. routes
- topical
- Indications
- chronic obstructive pulmonary disease, asthma
via ChEMBL · EBI
Wikidata facts
- Mass
- 485.173579
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₄H₃₃Cl₂NO₅
- isomeric SMILES
- C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNC[C@@H](C2=CC(=C(C=C2)O)CO)O)Cl
- canonical SMILES
- C1=CC(=C(C(=C1)Cl)COCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O)Cl
- Commons category
- Vilanterol
- World Health Organisation international non-proprietary name
- vilanterol
- physically interacts with
- adrenoceptor beta 2
- significant drug interaction
- sotalol
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{Drugbox | drug_name = | IUPAC_name = 4-{(1R)-2-[(6-{2-[(2,6-Dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol | image = Vilanterol.svg | image_class = skin-invert-image | width = 220 | alt = | caption = | tradename = | Drugs.com = | MedlinePlus = | pregnancy_AU = B3 | pregnancy_US = | pregnancy_category = | licence_EU = yes | legal_AU = S4 | legal_CA = | legal_UK = POM | legal_US = Rx-only | legal_status = Rx-only | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number = 503068-34-6 | ATCvet = | ATC_prefix = R03 | ATC_suffix = AK10 | ATC_supplemental = (+fluticasone) (+umeclidinium) | PubChem = 10184665 | UNII_Ref = | UNII = 028LZY775B | ChemSpiderID = 8360167 | IUPHAR_ligand = 7353 | DrugBank = | ChEBI = 75037 | ChEMBL = 1198857 | KEGG = D09696
| C = 24 | H = 33 | Cl = 2 | N = 1 | O = 5 | smiles = c1cc(c(c(c1)Cl)COCCOCCCCCCNC[C@@H](c2ccc(c(c2)CO)O)O)Cl | StdInChI = 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 | StdInChIKey = DAFYYTQWSAWIGS-DEOSSOPVSA-N }}
Excerpted from Wikipedia’s “vilanterol” article, available under the CC BY-SA 4.0 licence.