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873054-44-5

873054-44-5 Structure

873054-44-5 Structure
IdentificationBack Directory
[Name]

VX-770
[CAS]

873054-44-5
[Molecular Formula]

C24H28N2O3
[MDL Number]

MFCD17171361
[MOL File]

873054-44-5.mol
[Molecular Weight]

392.491
Chemical PropertiesBack Directory
[Boiling point ]

550.4±50.0 °C(Predicted)
[density ]

1.187
[pka]

11.08±0.23(Predicted)
Safety DataBack Directory
[HS Code ]

29333990
Hazard InformationBack Directory
[Description]

In January 2012, the US FDA approved ivacaftor for the treatment of cystic fibrosis (CF) in patients who have the G551D mutation of the CF transmembrane regulator (CFTR) and are at least 6 years old. Ivacaftor (also known as VX-770) is a CFTR potentiator that increases the open probability of CFTR, thus increasing chloride secretion particularly in the 5% of CF patients with the G551D/F508 gating/ processing mutation. Ivacaftor was discovered by medicinal chemistry optimization of a lead scaffold identified through high-throughput screening of a 228,000 compound collection. In cultured bronchial epithelial cells from a CF patient with F508del, ivacaftor increased chloride secretion (EC50=81 nM). Preparation of ivacaftor is accomplished via a multistep synthesis oftwointermediates, 4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 5-amino-di-tert-butylphenyl methyl carbonate, which are coupled using propane phosphonic acid anhydride (T3P) to afford the amide; deprotection of the phenol then provides ivacaftor.
[Originator]

Vertex Pharmaceuticals (United States)
[Uses]

Ivacaftor (VX-770, Kalydeco) is a potentiator of CFTR targeting G551D-CFTR and F508del-CFTR with EC50 of 100 nM and 25 nM, respectively
[Uses]

Ivacaftor is used in the treatment of cystic fibrosis.
[Definition]

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.
[Brand name]

Kalydeco
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