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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

Molecular Formula C15H12O2
Molecular Weight 224.2546
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C24H33Cl2NO5
Molecular Weight 486.429
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Chronic Obstructive Pulmonary Disease: 100 - 400 mcg GW642444H Twice daily in the morning.
Route of Administration: Respiratory
Substance Class Chemical
Record UNII
DB71X3OVN2
Record Status Validated (UNII)
Record Version