ceritinib   

GtoPdb Ligand ID: 7397

Synonyms: compound 15b [PMID 23742252] | LDK378 | NVP-LDK378-NX | Zykadia®
ceritinib is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Ceritinib is a novel, highly selective, second generation ALK inhibitor [2].
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 113.62
Molecular weight 557.22
XLogP 6.55
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(Oc1cc(C2CCNCC2)c(cc1Nc1ncc(c(n1)Nc1ccccc1S(=O)(=O)C(C)C)Cl)C)C
Isomeric SMILES CC(Oc1cc(C2CCNCC2)c(cc1Nc1ncc(c(n1)Nc1ccccc1S(=O)(=O)C(C)C)Cl)C)C
InChI InChI=1S/C28H36ClN5O3S/c1-17(2)37-25-15-21(20-10-12-30-13-11-20)19(5)14-24(25)33-28-31-16-22(29)27(34-28)32-23-8-6-7-9-26(23)38(35,36)18(3)4/h6-9,14-18,20,30H,10-13H2,1-5H3,(H2,31,32,33,34)
InChI Key VERWOWGGCGHDQE-UHFFFAOYSA-N
References
1. Friboulet L, Li N, Katayama R, Lee CC, Gainor JF, Crystal AS, Michellys PY, Awad MM, Yanagitani N, Kim S et al.. (2014)
The ALK inhibitor ceritinib overcomes crizotinib resistance in non-small cell lung cancer.
Cancer Discov, 4 (6): 662-673. [PMID:24675041]
2. Marsilje TH, Pei W, Chen B, Lu W, Uno T, Jin Y, Jiang T, Kim S, Li N, Warmuth M et al.. (2013)
Synthesis, structure-activity relationships, and in vivo efficacy of the novel potent and selective anaplastic lymphoma kinase (ALK) inhibitor 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (LDK378) currently in phase 1 and phase 2 clinical trials.
J. Med. Chem., 56 (14): 5675-90. [PMID:23742252]
3. Shaw AT, Kim DW, Mehra R, Tan DS, Felip E, Chow LQ, Camidge DR, Vansteenkiste J, Sharma S, De Pas T et al.. (2014)
Ceritinib in ALK-rearranged non-small-cell lung cancer.
N. Engl. J. Med., 370 (13): 1189-97. [PMID:24670165]
4. Thomas RK. (2014)
Overcoming drug resistance in ALK-rearranged lung cancer.
N. Engl. J. Med., 370 (13): 1250-1. [PMID:24670172]