936727-05-8

Basic information

• Product Name: Lumacaftor (VX-809)
• Synonyms: 3-(6-{[1-(2,2-Difluorobenzo[1,3]dioxol-5-yl)cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)be;VX-809 (LuMacaftor);3-[6-[[[1-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropyl]carbonyl]amino]-3-methyl-2-pyridinyl]benzoic acid VX 809 Lumacaftor;3-(6-{[1-(2;Lumacaftor VX809;VX 809, >=98%;VX-809, Lumacaftor, VRT 826809;3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methylpyridin-2-yl]benzoic acid
• CAS NO: 936727-05-8
• Molecular Formula: C24H18F2N2O5
• Molecular Weight: 452.4069264
• Product Categories: VX-809;Inhibitors
• Mol File: 936727-05-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 653.013 °C at 760 mmHg
• Flash Point: 348.73 °C
• Appearance: /
• Density: 1.51
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.95±0.10(Predicted)
• CAS DataBase Reference: Lumacaftor (VX-809)(CAS DataBase Reference)
• NIST Chemistry Reference: Lumacaftor (VX-809)(936727-05-8)
• EPA Substance Registry System: Lumacaftor (VX-809)(936727-05-8)

Safety Data

• Hazardous Substances Data: 936727-05-8(Hazardous Substances Data)

Usage

Uses

VX 809 is used in the stabilization of the CFTR protein used in the treatment of cystic fibrosis.

Definition

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid with the aromatic amino group of 3-(6-amino-3-methylpyridin-2-yl)benzoic acid. Used for the treatment of cystic fi rosis.

Biological Activity

vx-809 is a cftr corrector that partially restores the function of f508del-cftr. in fischer rat thyroid (frt) cells, it increases f508del-cftr maturation at ec50 of 0.1 μm, and elevates f508del-cftr–mediated chloride transport at ec50 of 0.5 μm [1]. it has no effect of other ion channels (herg), transporter (p-gp) and disease-causing mislocalized proteins (α1-antitrypsin z mutant) [1]. vx-809 stabilizes n-terminal fragment of cftr that contain msd1 by altering its protein conformation [2, 3].homozygous f508del-cftr is the most common mutation in cystic fibrosis (cf) patients, accounting for 66–70% of cf cases worldwide. in cultured human bronchial epithelial cells that are homozygous for f508del, vx-809 restored the cftr function and improved chloride and fluid transport [1]. the combination of cftr potentiators and vx-809 further improved the function of f508del-cftr [4].vx-809 has been tested in several

InChI:InChI=1/C24H18F2N2O5/c1-13-5-8-19(27-20(13)14-3-2-4-15(11-14)21(29)30)28-22(31)23(9-10-23)16-6-7-17-18(12-16)33-24(25,26)32-17/h2-8,11-12H,9-10H2,1H3,(H,29,30)(H,27,28,31)

Upstream product

• 1160221-25-9 tert-butyl 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoate 
• 936727-68-3 N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide 
• 25487-66-5 3-Carboxyphenylboronic acid 
• 269409-73-6 3-carboxyphenylboronic acid pinacol ester 
• 89466-17-1 6-amino-2-bromo-3-methylpyridine 
• 19230-57-0 2-bromo-3-methylpyridine 1-oxide 
• 442129-37-5 6-amino-2-chloro-3-methylpyridine 
• 18368-76-8 2 chloro-3-methylpyridine 
• 91668-83-6 2-Chloro-3-methylpyridine N-oxide 
• 72768-97-9 (2,2-difluoro-1,3-benzodioxol-5-yl)methanol 
• 220210-56-0 3-(tert-butoxycarbonyl)phenylboronic acid 
• 68119-31-3 2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile 
• 656-46-2 2,2-difluoro-1,3-benzodioxole-5-carboxylic acid 
• 1004294-65-8 1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)cyclopropane carboxylic acid chloride 

Relevant articles and documents

PROCESS AND CRYSTALLINE FORMS OF LUMACAFTOR

The present invention generally relates to crystalline forms of Lumacaftor, processes for its preparation and pharmaceutical compositions thereof. The present invention also relates to an improved process for preparation of Lumacaftor.

AMORPHOUS LUMACAFTOR AND ITS SOLID DISPERSION

The present invention provides a novel amorphous form of lumacaftor and its preparation by various methods. The patent invention also relates to novel lumacaftor hydrobromide crystalline form A and process for its preparation. The present invention relates to amorphous lumacaftor premixed with an excipient and process for the preparation of the premix.

PROCESS FOR THE PREPARATION OF LUMACAFTOR

The present disclosure relates to processes for the preparation of lumacaftor useful for treating a cystic fibrosis transmembrane conductance regulator (CFTR)-mediated disease such as cystic fibrosis. The present disclosure also provides intermediates useful in the preparation of lumacaftor