entrectinib   Click here for help

GtoPdb Ligand ID: 8290

Synonyms: NMS-E628 | Rozlytrek® | RXDX-101
Approved drug PDB Ligand
entrectinib is an approved drug (Japan and FDA (2019), EMA (2020))
Compound class: Synthetic organic
Comment: Entrectinib is an oral, brain penetrant, receptor tyrosine kinase (RTK) inhibitor that targets solid tumours that harbour activating alterations in NTRK1, NTRK2, NTRK3 (the Trk family RTKs), ROS1 or ALK [6]. NTRK1 fusion proteins are becoming recognised as oncogenic-drivers in NSCLC [3], so the ability of the compound to target these and ALK- and ROS1-rearrangements suggests it has the potential to become a useful oncology agent.
More recently entrectinib has been shown to inhibit NLRP3 inflammasome assembly and activation via a direct interaction with NIMA related kinase 7 (NEK7) that disrupts the NLRP3-NEK7 interaction [5]. This discovery suggests a role for entrectinib as an intervention for inflammasome-related diseases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 85.52
Molecular weight 560.27
XLogP 6.13
No. Lipinski's rules broken 1
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Canonical SMILES CN1CCN(CC1)c1ccc(c(c1)NC1CCOCC1)C(=O)Nc1n[nH]c2c1cc(cc2)Cc1cc(F)cc(c1)F
Isomeric SMILES CN1CCN(CC1)c1ccc(c(c1)NC1CCOCC1)C(=O)Nc1n[nH]c2c1cc(cc2)Cc1cc(F)cc(c1)F
InChI InChI=1S/C31H34F2N6O2/c1-38-8-10-39(11-9-38)25-3-4-26(29(19-25)34-24-6-12-41-13-7-24)31(40)35-30-27-17-20(2-5-28(27)36-37-30)14-21-15-22(32)18-23(33)16-21/h2-5,15-19,24,34H,6-14H2,1H3,(H2,35,36,37,40)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan and FDA (2019), EMA (2020))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10132 entrectinib
Synonyms Click here for help
NMS-E628 | Rozlytrek® | RXDX-101
Database Links Click here for help
CAS Registry No. 1108743-60-7
ChEMBL Ligand CHEMBL1983268
DrugCentral Ligand 5345
GtoPdb PubChem SID 252166502
PubChem CID 25141092
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