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SML3389

Vilanterol trifenatate

≥95% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C24H33Cl2NO5·C20H16O2
CAS Number:
503070-58-4
Molecular Weight:
774.77
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD21362970
Assay:
≥95% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
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Quality Level

100

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

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

InChI key

KLOLZALDXGTNQE-JIDHJSLPSA-N

Related Categories

General description

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).

Biochem/physiol Actions

Potent and selective, beta2 (β2)-adrenoceptor agonist in vitro and in vivo.
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).

signalword

Warning

Hazard Classifications

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

target_organs

Cardiovascular

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000525310
0000525310
0000501355
0000501355
0000427586

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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)
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)
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

Global Trade Item Number

SKUGTIN
SML3389-50MG04065268564486
SML3389-10MG04065268564479

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