canertinib   Click here for help

GtoPdb Ligand ID: 5675

Synonyms: CI 1033 | CI-1033 | PD 183805 dihydrochloride [6]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Canertinib is an irreversible inhibitor which blocks signal transduction through all four members of the erbB family [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 88.61
Molecular weight 485.16
XLogP 3.08
No. Lipinski's rules broken 0
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Canonical SMILES C=CC(=O)Nc1cc2c(ncnc2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
Isomeric SMILES C=CC(=O)Nc1cc2c(ncnc2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
InChI InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29)
1. Allen LF, Lenehan PF, Eiseman IA, Elliott WL, Fry DW. (2002)
Potential benefits of the irreversible pan-erbB inhibitor, CI-1033, in the treatment of breast cancer.
Semin Oncol, 29 (3 Suppl 11): 11-21. [PMID:12138393]
2. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM, Pallares G, Hocker M, Treiber DK, Zarrinkar PP. (2011)
Comprehensive analysis of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1046-51. [PMID:22037378]
3. Nordigården A, Zetterblad J, Trinks C, Gréen H, Eliasson P, Druid P, Lotfi K, Rönnstrand L, Walz TM, Jönsson JI. (2011)
Irreversible pan-ERBB inhibitor canertinib elicits anti-leukaemic effects and induces the regression of FLT3-ITD transformed cells in mice.
Br J Haematol, 155 (2): 198-208. [PMID:21848891]
4. Rao GS, Murray S, Ethier SP. (2000)
Radiosensitization of human breast cancer cells by a novel ErbB family receptor tyrosine kinase inhibitor.
Int J Radiat Oncol Biol Phys, 48 (5): 1519-28. [PMID:11121658]
5. Rixe O, Franco SX, Yardley DA, Johnston SR, Martin M, Arun BK, Letrent SP, Rugo HS. (2009)
A randomized, phase II, dose-finding study of the pan-ErbB receptor tyrosine-kinase inhibitor CI-1033 in patients with pretreated metastatic breast cancer.
Cancer Chemother Pharmacol, 64 (6): 1139-48. [PMID:19294387]
6. Smaill JB, Rewcastle GW, Loo JA, Greis KD, Chan OH, Reyner EL, Lipka E, Showalter HD, Vincent PW, Elliott WL et al.. (2000)
Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)pyrido[3,2-d]pyrimidine-6-acrylamides bearing additional solubilizing functions.
J Med Chem, 43 (7): 1380-97. [PMID:10753475]
7. Trinks C, Severinsson EA, Holmlund B, Gréen A, Gréen H, Jönsson JI, Hallbeck AL, Walz TM. (2011)
The pan-ErbB tyrosine kinase inhibitor canertinib induces caspase-mediated cell death in human T-cell leukemia (Jurkat) cells.
Biochem Biophys Res Commun, 410 (3): 422-7. [PMID:21669187]
8. Wodicka LM, Ciceri P, Davis MI, Hunt JP, Floyd M, Salerno S, Hua XH, Ford JM, Armstrong RC, Zarrinkar PP et al.. (2010)
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
Chem Biol, 17 (11): 1241-9. [PMID:21095574]