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
Click here for structure editor
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
Bioactivity Comments
In vitro, of 13 of most frequent imatinib-resistant Bcr-Abl point mutations, bafetinib inhibits all but one, Thr315Ile, and in preclinical studies it proved to be ≥10-fold more potent than imatinib in vivo [6]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
LYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.0 pIC50 - 1
pIC50 8.0 (IC50 1.1x10-8 M) [1]
ABL proto-oncogene 1, non-receptor tyrosine kinase Hs Inhibitor Inhibition 7.6 – 8.2 pIC50 - 1,3
pIC50 7.6 – 8.2 (IC50 2.6x10-8 – 5.8x10-9 M) [1,3]