vecabrutinib   Click here for help

GtoPdb Ligand ID: 10231

Synonyms: BIIB-062 | BIIB062 | SNS-062 | SNS062
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vecabrutinib (SNS-062) is a second generation, noncovalent (reversible) Bruton's tyrosine kinase (BTK) inhibitor that is being developed by Sunesis Pharmaceuticals as a therapeutic for B cell malignancies that have developed resistance to first generation BTK inhibitors such as ibrutinib, through acquisition of the Cys481Ser mutation in the enzyme's active site. The structure presented here was obtained by searching PubChem using the IUPAC structure that was submitted to the WHO for the INN vecabrutinib. Sunesis' website associates the INN with the research code SNS-062 [3]. Formal name-to-structure identification and pharmacological analysis are yet to be disclosed in a peer-reviewed publication. Patent interrogation identifies example I-1 in Biogen/Sunesis' patent WO2013185084A1 as a structure match to vecabrutinib [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 130.47
Molecular weight 529.16
XLogP 3.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1cc(NC2CCCN(C2=O)C2CN(CCC2C(=O)N)c2ncnc(c2F)N)cc(c1)C(F)(F)F
Isomeric SMILES Clc1cc(N[C@@H]2CCCN(C2=O)[C@H]2CN(CC[C@@H]2C(=O)N)c2ncnc(c2F)N)cc(c1)C(F)(F)F
InChI InChI=1S/C22H24ClF4N7O2/c23-12-6-11(22(25,26)27)7-13(8-12)32-15-2-1-4-34(21(15)36)16-9-33(5-3-14(16)19(29)35)20-17(24)18(28)30-10-31-20/h6-8,10,14-16,32H,1-5,9H2,(H2,29,35)(H2,28,30,31)/t14-,15+,16-/m0/s1
InChI Key QLRRJMOBVVGXEJ-XHSDSOJGSA-N