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].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10643 vecabrutinib
Synonyms Click here for help
BIIB-062 | BIIB062 | SNS-062 | SNS062
Database Links Click here for help
CAS Registry No. 1510829-06-7 (source: WHO INN record)
GtoPdb PubChem SID 381744913
PubChem CID 72547837
Search Google for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N
Search Google for chemicals with the same backbone QLRRJMOBVVGXEJ
Search PubMed clinical trials vecabrutinib
Search PubMed titles vecabrutinib
Search PubMed titles/abstracts vecabrutinib
UniChem Compound Search for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N
UniChem Connectivity Search for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N