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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H33Cl2NO5.C15H12O2
Molecular Weight 710.683
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VILANTEROL .ALPHA.-PHENYL CINNAMATE

SMILES

OC(=O)C(=C\C1=CC=CC=C1)\C2=CC=CC=C2.OCC3=C(O)C=CC(=C3)[C@@H](O)CNCCCCCCOCCOCC4=C(Cl)C=CC=C4Cl

InChI

InChIKey=KAMFDHLRBHTIMJ-AZDLLSQWSA-N
InChI=1S/C24H33Cl2NO5.C15H12O2/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;16-15(17)14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h5-9,14,24,27-30H,1-4,10-13,15-17H2;1-11H,(H,16,17)/b;14-11+/t24-;/m0./s1

HIDE SMILES / InChI
VILANTEROL α-PHENYL CINNAMATE (GW642444H), originally developed by GlaxoSmithKline, is a long-acting β2 adrenoceptor agonist for once daily treatment of COPD and asthma. Phase III clinical trials are ongoing. GW642444H is Vilanterol a-phenylcinnimate salt. In clinical studies the study drug may been given as a dry powder in the form of either the ‘H’ salt (with the excipient lactose), or in the form of the ‘M’ salt (with the excipients lactose and cellobiose octaacetate). 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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Novel long-acting bronchodilators for COPD and asthma.
2008 Oct
Novel bronchodilators in asthma.
2010 Jan

Sample Use Guides

Chronic Obstructive Pulmonary Disease: 100 - 400 mcg GW642444H Twice daily in the morning.
Route of Administration: Respiratory
Name Type Language
VILANTEROL .ALPHA.-PHENYL CINNAMATE
Common Name English
GW642444H
Code English
BENZENEACETIC ACID, .ALPHA.-(PHENYLMETHYLENE)-, COMPD. WITH (.ALPHA.1R)-.ALPHA.1-(((6-(2-((2,6-DICHLOROPHENYL)METHOXY)ETHOXY)HEXYL)AMINO)METHYL)-4-HYDROXY-1,3-BENZENEDIMETHANOL (1:1)
Common Name English
GW-642444H
Code English
Code System Code Type Description
FDA UNII
DB71X3OVN2
Created by admin on Sat Dec 16 03:08:06 GMT 2023 , Edited by admin on Sat Dec 16 03:08:06 GMT 2023
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EPA CompTox
DTXSID40198319
Created by admin on Sat Dec 16 03:08:06 GMT 2023 , Edited by admin on Sat Dec 16 03:08:06 GMT 2023
PRIMARY
CAS
503070-59-5
Created by admin on Sat Dec 16 03:08:06 GMT 2023 , Edited by admin on Sat Dec 16 03:08:06 GMT 2023
PRIMARY
PUBCHEM
46832503
Created by admin on Sat Dec 16 03:08:06 GMT 2023 , Edited by admin on Sat Dec 16 03:08:06 GMT 2023
PRIMARY