Entrectinib

Base Information

• Chemical Name: Entrectinib
• CAS No.: 1108743-60-7
• Molecular Formula: C31H34F2N6O2
• Molecular Weight: 560.647
• Mol file: 1108743-60-7.mol

Synonyms:Entrectinib;Entrectinib(NMS-E628);N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzamide;RXDX-101;Entrectinib,NMS-E628,RXDX-101

Chemical Property of Entrectinib

Chemical Property:

• Boiling Point: 717.5±60.0 °C(Predicted)
• PKA: 12.01±0.43(Predicted)
• PSA: 85.52000
• Density: 1.340±0.06 g/cm3(Predicted)
• LogP: 5.17580
• Solubility.: ≥28.05 mg/mL in DMSO; insoluble in H2O; ≥9.82 mg/mL in EtOH with ultrasonic

Purity/Quality:

99% ^*data from raw suppliers

Entrectinib 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Entrectinib is used to treat metastatic (lung cancer that has already spread) non-small cell lung cancer (NSCLC) that is caused by a gene called ROS1. This medicine is also used to treat solid tumors (cancer) that are caused by certain abnormal NTRK genes and have spread or if surgery to remove the cancer is likely to cause severe complications, and there is no acceptable treatment option or the cancer grew or spread on other treatments. Entrectinib is an inhibitor of TrkA (IC50 = 1.7 nM), TrkB (IC50 = 0.1 nM), and TrkC (IC50 = 0.1 nM), as well as C-ros oncogene 1 (ROS1; IC50 = 0.2 nM) and anaplastic lymphoma kinase (ALK; IC50 = 1.6 nM). Entrectinib blocks proliferation of ALK-dependent cell lines, including those with L1196M or C1156Y resistance mutations, and inhibits ALK‐dependent signaling. It has been shown to inhibit the growth of a non-small cell lung cancer cell line bearing an EML4-ALK rearrangement. In mice bearing various Trk, ROS1, or ALK-driven xenografts, entrectinib has been shown to induce tumor regression. Entrectinib (RXDX-101, Ignyta Pharmaceuticals, San Diego, CA, USA) is a small molecule that inhibits the tyrosine kinases TRKA/B/C, ROS1, and ALK (Table?1). It has a preclinical median inhibitory concentration (IC50) of 7?nm against ROS1, higher than crizotinib [95, 96]. Entrectinib was specifically designed to cross the blood-brain barrier [95].
• Uses: Entrectinib, also known as RXDX-101 and NMS-E628, is an oral small molecule inhibitor of TrkA, TrkB and TrkC, as well as ROS1 and ALK, with high potency and selectivity. RXDX-101 has demonstrated potent pharmacological activity in preclinical studies and has the potential to be first-in-class against the Trk family of kinases. PXDX-101 has been well tolerated in patients with advanced solid tumors. PXDX-101 is currently in clinical trials, and is being developed by Ignyta.
• Clinical Use: Entrectinib demonstrated potent antitumor effects in tumor cell lines and patient-derived xenograft (PDX) tumor models in preclinical studies. Furthermore, entrectinib can cross the blood–brain barrier (BBB) to impact primary brain tumors and brain metastases in patients with NTRK1/ NTRK2/NTRK3, ROS1, and ALK fusion-driven cancers.

Technology Process of Entrectinib

There total 25 articles about Entrectinib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.2%

C39H40F2N6O4 → N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)amino)benzamide (1108743-60-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; under 760.051 Torr; Inert atmosphere;

Reference yield: 78.0%

N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzamide (1108745-38-5) → N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)amino)benzamide (1108743-60-7)

Guidance literature:

With triethylamine; In methanol; at 65 ℃; for 2h; Product distribution / selectivity;

Reference yield: 78.0%

5-(3,5-difluoro-benzyl)-1H-indazol-3-ylamine (1108745-30-7) + C2HF3O2*C19H23ClF3N3O3 → N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)amino)benzamide (1108743-60-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -20 ℃; for 4h;

DOI:10.1021/acs.jmedchem.6b00064

upstream raw materials:

Tetrahydro-4H-pyran-4-one

2-amino-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide

N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzamide

4-(4-methylpiperazine-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzoic acid trifluoroacetic acid salt

Downstream raw materials:

ethyl 5-(3,5-difluorobenzyl)-3-({[4-(4-methylpiperazin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)phenyl]carbonyl}amino)-1H-indazole-1-carboxylate

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