bafetinib   

GtoPdb Ligand ID: 7906

Synonyms: INNO-406 | Lyn-IN-1 | NS-187
Compound class: Synthetic organic
Comment: Bafetinib is a second-generation, dual Lyn/Abl kinase inhibitor [1,6] with therapeutic.potential for the treatment of imatinib-resistant or -intolerant B-cell chronic lymphocytic leukemia (CLL), and prostate cancer. Data indicate that bafetinib crosses the blood-brain-barrier, reaching therapeutic concentration, so the drug's potential for treatment of brain tumours is also under investigation.

Note that we have mapped the chemical structure using the updated CAS registry number stipulated in INN proposed list 101 (2009) to the CID specified here, but the name maps to four other CIDs in PubChem.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 99.17
Molecular weight 576.26
XLogP 3.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN(C1CCN(C1)Cc1ccc(cc1C(F)(F)F)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cncnc1)C)C
Isomeric SMILES CN([C@H]1CCN(C1)Cc1ccc(cc1C(F)(F)F)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cncnc1)C)C
InChI InChI=1S/C30H31F3N8O/c1-19-4-7-23(13-27(19)39-29-36-10-8-26(38-29)22-14-34-18-35-15-22)37-28(42)20-5-6-21(25(12-20)30(31,32)33)16-41-11-9-24(17-41)40(2)3/h4-8,10,12-15,18,24H,9,11,16-17H2,1-3H3,(H,37,42)(H,36,38,39)/t24-/m0/s1
InChI Key ZGBAJMQHJDFTQJ-DEOSSOPVSA-N
References
1. Horio T, Hamasaki T, Inoue T, Wakayama T, Itou S, Naito H, Asaki T, Hayase H, Niwa T. (2007)
Structural factors contributing to the Abl/Lyn dual inhibitory activity of 3-substituted benzamide derivatives.
Bioorg. Med. Chem. Lett., 17 (10): 2712-7. [PMID:17376680]
2. Kantarjian H, le Coutre P, Cortes J, Pinilla-Ibarz J, Nagler A, Hochhaus A, Kimura S, Ottmann O. (2010)
Phase 1 study of INNO-406, a dual Abl/Lyn kinase inhibitor, in Philadelphia chromosome-positive leukemias after imatinib resistance or intolerance.
Cancer, 116 (11): 2665-72. [PMID:20310049]
3. Kimura S, Naito H, Segawa H, Kuroda J, Yuasa T, Sato K, Yokota A, Kamitsuji Y, Kawata E, Ashihara E et al.. (2005)
NS-187, a potent and selective dual Bcr-Abl/Lyn tyrosine kinase inhibitor, is a novel agent for imatinib-resistant leukemia.
Blood, 106 (12): 3948-54. [PMID:16105974]
4. Niwa T, Asaki T, Kimura S. (2007)
NS-187 (INNO-406), a Bcr-Abl/Lyn dual tyrosine kinase inhibitor.
Anal Chem Insights, 2: 93-106. [PMID:19662183]
5. Rix U, Remsing Rix LL, Terker AS, Fernbach NV, Hantschel O, Planyavsky M, Breitwieser FP, Herrmann H, Colinge J, Bennett KL et al.. (2010)
A comprehensive target selectivity survey of the BCR-ABL kinase inhibitor INNO-406 by kinase profiling and chemical proteomics in chronic myeloid leukemia cells.
Leukemia, 24 (1): 44-50. [PMID:19890374]
6. Santos FP, Kantarjian H, Cortes J, Quintas-Cardama A. (2010)
Bafetinib, a dual Bcr-Abl/Lyn tyrosine kinase inhibitor for the potential treatment of leukemia.
Curr Opin Investig Drugs, 11 (12): 1450-65. [PMID:21154127]