crizotinib   Click here for help

GtoPdb Ligand ID: 4903

Synonyms: (R)-crizotinib | PF 2341066 | PF-02341066 | PF-2341066 | PF2341066 | Xalkori®
Approved drug PDB Ligand Immunopharmacology Ligand
crizotinib is an approved drug (FDA (2011), EMA (2012))
Compound class: Synthetic organic
Comment: Critzotinib is a Type-1 kinase inhibitor and was first approved by the FDA in 2011. It inhibits ALK, cMET and ROS1 receptor tyrosine kinases. Critzotinib is a chiral molecule that exploits the three-dimensional space of the ATP pocket to achieve optimal potency and selectivity [6]. The R-enantiomer as shown here exhibits better potency than the either the racemate or S-isomer and the approved drug should contain only the R-enantiomer.
Pfizer developed the 3rd generation ALK inhibitor lorlatinib as a follow-up to critzotinib, and this new drug has been reported to outperfom its predecessor in lung cancer.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 77.99
Molecular weight 449.12
XLogP 4.83
No. Lipinski's rules broken 0
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Canonical SMILES Nc1ncc(cc1OC(c1c(Cl)ccc(c1Cl)F)C)c1cnn(c1)C1CCNCC1
Isomeric SMILES Nc1ncc(cc1O[C@@H](c1c(Cl)ccc(c1Cl)F)C)c1cnn(c1)C1CCNCC1
InChI InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2011), EMA (2012))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9301 crizotinib
Synonyms Click here for help
(R)-crizotinib | PF 2341066 | PF-02341066 | PF-2341066 | PF2341066 | Xalkori®
Database Links Click here for help
CAS Registry No. 877399-52-5
ChEMBL Ligand CHEMBL601719
DrugCentral Ligand 4187
GtoPdb PubChem SID 178101602
PubChem CID 11626560
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SynPHARM 79022 (in complex with anaplastic lymphoma receptor tyrosine kinase)
78753 (in complex with MET proto-oncogene, receptor tyrosine kinase)
79023 (in complex with MET proto-oncogene, receptor tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey KTEIFNKAUNYNJU-GFCCVEGCSA-N
UniChem Connectivity Search for chemical match using the InChIKey KTEIFNKAUNYNJU-GFCCVEGCSA-N
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Crizotinib (links to external site)
Cat. No. 4368