Ivacaftor (VX-770) , ≥98% , 873054-44-5

Synonym(s):
CFTR Potentiator, VX-770 - CAS 873054-44-5 - Calbiochem;N-(5-Hydroxy-2,4- bis(2-methyl-2-propanyl)phenyl]-4-oxo-1,4-dihydro-3-quinolinecarboxamide, Cystic Fibrosis Transmembrane Conductance Regulator Potentiator, VX 770, Ivacaftor, Kalydeco;N-(5-Hydroxy-2,4-bis(2-methyl-2-propanyl)phenyl]-4-oxo-1,4-dihydro-3-quinolinecarboxamide, Cystic Fibrosis Transmembrane Conductance Regulator Potentiator, VX 770, Ivacaftor, Kalydeco

CAS NO.：873054-44-5

Empirical Formula: C24H28N2O3

Molecular Weight: 392.49

MDL number: MFCD17171361

PRODUCT Properties

• Melting point: 212-215°C
• Boiling point: 550.4±50.0 °C(Predicted)
• Density: 1.187
• storage temp.: Refrigerator
• solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• pka: 11.08±0.23(Predicted)
• form: Solid
• color: White to Light Brown
• InChI: InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)
• InChIKey: PURKAOJPTOLRMP-UHFFFAOYSA-N
• SMILES: N1C2=C(C=CC=C2)C(=O)C(C(NC2=CC(O)=C(C(C)(C)C)C=C2C(C)(C)C)=O)=C1

Description and Uses

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.

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

Safety

• Symbol(GHS): GHS08,GHS07
• Signal word: Warning
• Hazard statements: H361-H319-H315-H335
• Precautionary statements: P264-P280-P302+P352-P321-P332+P313-P362-P201-P202-P281-P308+P313-P405-P501-P264-P280-P305+P351+P338-P337+P313P
• HS Code: 29333990