alectinib   Click here for help

GtoPdb Ligand ID: 7739

Synonyms: AF802 | Alecensa® | CH5424802
Approved drug PDB Ligand
alectinib is an approved drug (FDA (2015), EMA (2017), Japan (unknown))
Compound class: Synthetic organic
Comment: Alectinib is a second generation ALK inhibitor. It was developed to inhibit the expression of the mutated ALK gene that causes growth of some non-small cell lung cancers, in patients whose cancer has become resistant to the older ALK inhibitor, crizotinib [2,5]. However, additional mutations may develop which confer alecitinib resistance [1]. Cells harbouring these novel mutations are reported to be sensitive to ceritinib and other next-generation ALK tyrosine kinase inhibitors [1]. The identification of the mechanisms by which acquired tumour resistance occurs highlights the importance of being able to use the correct drug for the correct patient to maximise the clinical benefit [4]
The design and synthesis of alectinib (CH5424802) is described in [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 72.36
Molecular weight 482.27
XLogP 5.37
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCc1cc2C(=O)c3c4ccc(cc4[nH]c3C(c2cc1N1CCC(CC1)N1CCOCC1)(C)C)C#N
Isomeric SMILES CCc1cc2C(=O)c3c4ccc(cc4[nH]c3C(c2cc1N1CCC(CC1)N1CCOCC1)(C)C)C#N
InChI InChI=1S/C30H34N4O2/c1-4-20-16-23-24(17-26(20)34-9-7-21(8-10-34)33-11-13-36-14-12-33)30(2,3)29-27(28(23)35)22-6-5-19(18-31)15-25(22)32-29/h5-6,15-17,21,32H,4,7-14H2,1-3H3
InChI Key KDGFLJKFZUIJMX-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2015), EMA (2017), Japan (unknown))
IUPAC Name Click here for help
9-ethyl-6,6-dimethyl-8-(4-morpholin-4-ylpiperidin-1-yl)-11-oxo-5H-benzo[b]carbazole-3-carbonitrile
International Nonproprietary Names Click here for help
INN number INN
9699 alectinib
Synonyms Click here for help
AF802 | Alecensa® | CH5424802
Database Links Click here for help
CAS Registry No. 1256580-46-7
ChEMBL Ligand CHEMBL1738797
DrugCentral Ligand 4937
GtoPdb PubChem SID 223366072
PubChem CID 49806720
RCSB PDB Ligand EMH
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