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].

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ceritinib

2D Structure

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2014), EMA (2015))
IUPAC Name
5-chloro-2-N-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine
International Nonproprietary Names
INN number INN
9817 ceritinib
Synonyms
compound 15b [PMID 23742252] | LDK378 | NVP-LDK378-NX | Zykadia®
Comments
Ceritinib is a novel, highly selective, second generation ALK inhibitor [2].
Database Links
CAS Registry No. 1032900-25-6
ChEMBL Ligand CHEMBL2403108
DrugCentral Ligand 4866
GtoPdb PubChem SID 178103969
PubChem CID 57379345
RCSB PDB Ligand 4MK
Search Google for chemical match using the InChIKey VERWOWGGCGHDQE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VERWOWGGCGHDQE
Search PubMed clinical trials ceritinib
Search PubMed titles ceritinib
Search PubMed titles/abstracts ceritinib
Search UniChem for chemical match using the InChIKey VERWOWGGCGHDQE-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone VERWOWGGCGHDQE
SynPHARM 79503 (in complex with anaplastic lymphoma receptor tyrosine kinase)
Wikipedia Ceritinib

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Tocris
Ceritinib
Cat. No. 6905