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Key Documents

SML3389

Sigma-Aldrich

Vilanterol trifenatate

≥95% (HPLC)

Synonyme(s) :

4-[(1R)-2-({6-[(2-{[(2,6-Dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol, triphenylacetate salt, GW 642444 trifenatate, GW 642444M, GW-642444 trifenatate, GW-642444M, GW642444 trifenatate, GW642444M, Vilanterol triphenylacetate sal

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About This Item

Formule empirique (notation de Hill):
C24H33Cl2NO5·C20H16O2
Numéro CAS:
Poids moléculaire :
774.77
Numéro MDL:
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

OC(C(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)=O.ClC(C=CC=C4Cl)=C4COCCOCCCCCCNC[C@@H](C5=CC(CO)=C(C=C5)O)O

InChI

1S/C24H33Cl2NO5.C20H16O2/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;21-19(22)20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h5-9,14,24,27-30H,1-4,10-13,15-17H2;1-15H,(H,21,22)/t24-;/m0./s1

Clé InChI

KLOLZALDXGTNQE-JIDHJSLPSA-N

Description générale

Vilanterol trifenatate is a potent and selective beta2 (β2)-adrenoceptor agonist. This bioactive small molecule has been shown to stimulate cellular cAMP accumulation in CHO cells that express human beta2 adrenoceptors, while not having the same effect on beta1 or beta3 receptors (pEC50 = 9.4/β2, 6.4/β1, 6.1/β3). Vilanterol can reduce the contraction of electrically stimulated guinea pig trachea strips and exhibits in vivo therapeutic efficacy in an asthma model in guinea pigs with histamine-induced bronchospasm (EC90 = nebulizer concentration 30 μM). Additionally, Vilanterol trifenatate acts as a substrate for P-glycoprotein (PgP).

Actions biochimiques/physiologiques

Vilanterol is a potent and selective, beta2 (β2)-adrenoceptor agonist that stimulates cellular cAMP accumulation in CHO cells expressing human beta2, but not beta1 or beta3, adrenoceptor (pEC50 = 9.4/β2, 6.4/β1, 6.1/β3). Vilanterol inhibits the contraction of electrically stimulated guinea pig trachea strips and displays in vivo therapeutic efficacy in a guinea pig asthma model of histamine-induced bronchospasm (EC90 = nebulizer concentration 30 μM).

Pictogrammes

Health hazardExclamation markEnvironment

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Irrit. 2 - STOT SE 2

Organes cibles

Cardiovascular

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

Mario Cazzola et al.
British journal of pharmacology, 163(1), 4-17 (2011-01-15)
Despite the passionate debate over the use of β(2) -adrenoceptor agonists in the treatment of airway disorders, these agents are still central in the symptomatic management of asthma and COPD. A variety of β(2) -adrenoceptor agonists with long half-lives, also
Panayiotis A Procopiou et al.
Journal of medicinal chemistry, 53(11), 4522-4530 (2010-05-14)
A series of saligenin beta(2) adrenoceptor agonist antedrugs having high clearance were prepared by reacting a protected saligenin oxazolidinone with protected hydroxyethoxyalkoxyalkyl bromides, followed by removal of the hydroxy-protecting group, alkylation, and final deprotection. The compounds were screened for beta(2)
The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of inhaled fluticasone furoate and vilanterol trifenatate in healthy subjects
Kempsford R, et al.
British Journal of Clinical Pharmacology (2012)

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