vamotinib   Click here for help

GtoPdb Ligand ID: 9792

Synonyms: compound 1 (Table 1) [WO2012173521] | PF-114 | PF114
Compound class: Synthetic organic
Comment: Vamotinib (PF-114) is a third generation BCR-ABL kinase inhibitor [2-3]. It was designed to target wild-type resistance mutations in BCR-ABL (including the T315I gatekeeper mutation) in order to overcome drug resistance in Philadelphia chromosome positive (Ph+) leukemias. The chemical strucure is claimed in patent WO2012173521 where it is the first compound listed in Table 1 of the patent [1]. Off-targets identified by kinase profile screening include ABL2/ARG, DDR1, DDR2, FMS, FRK/PTK5, LCK, LYN, LYNB, PDGFRα and RET which had <10% residual activity when exposed to 100 nM of inhibitor [3]. We matched PF-114's chemical structure to the INN 'vamotinib' that was released in the WHO's proposed INN list 127 (21 July 2022).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 65.77
Molecular weight 532.22
XLogP 7.11
No. Lipinski's rules broken 1
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Canonical SMILES CN1CCN(CC1)Cc1ccc(cc1C(F)(F)F)NC(=O)c1ccc(c(c1)C#Cc1nnc2n1cccc2)C
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1C(F)(F)F)NC(=O)c1ccc(c(c1)C#Cc1nnc2n1cccc2)C
InChI InChI=1S/C29H27F3N6O/c1-20-6-7-22(17-21(20)9-11-27-35-34-26-5-3-4-12-38(26)27)28(39)33-24-10-8-23(25(18-24)29(30,31)32)19-37-15-13-36(2)14-16-37/h3-8,10,12,17-18H,13-16,19H2,1-2H3,(H,33,39)
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
12273 vamotinib
Synonyms Click here for help
compound 1 (Table 1) [WO2012173521] | PF-114 | PF114
Database Links Click here for help
CAS Registry No. 1416241-23-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297478
DrugBank Ligand DB15396
GtoPdb PubChem SID 354702265
PubChem CID 71475839
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