rezivertinib   Click here for help

GtoPdb Ligand ID: 10628

Synonyms: example 1 [WO2016094821A2]
Compound class: Synthetic organic
Comment: The chemical structure submitted to the WHO for INN rezivertinib, is identical to the structure of example 1 that is claimed in patent WO2016094821A2 by Beta Pharma [1]. This patent claims novel EGFR inhibitors that are active against mutated EGFRs that are found in cancers, i.e. third generation EGFR inhibitors. From Beta Pharma's declared pipeline, example 1 is likely to be BPI-7711, which is being investigated for the treatment of EGFRT790M-mutant non-small cell lung cancer. We await formal name>structure confirmation. Experimental evidence in WO2016094821A2 indicates that example 1 is orally bioavailable.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 93.54
Molecular weight 486.24
XLogP 3.3
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES C=CC(=O)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(cc1OCCN(C)C)OC
Isomeric SMILES C=CC(=O)Nc1cc(Nc2nccc(n2)c2cn(c3c2cccc3)C)c(cc1OCCN(C)C)OC
InChI InChI=1S/C27H30N6O3/c1-6-26(34)29-22-15-21(24(35-5)16-25(22)36-14-13-32(2)3)31-27-28-12-11-20(30-27)19-17-33(4)23-10-8-7-9-18(19)23/h6-12,15-17H,1,13-14H2,2-5H3,(H,29,34)(H,28,30,31)
InChI Key BPMZUKYFIDPLEA-UHFFFAOYSA-N
Bioactivity Comments
Example 1 exhibits anti-proliferative activity in vitro and in vivo (in mice with HCC827 and H1975 cell xenograft tumours) [1]. HCC827 cells harbour an EGFR with E746-A750 deletion; H1975 cells express the L858R/T790M double mutation). The in vitro anti-proliferative effect of example 1 is more pronounced in H1975 cell culture than in wild type EGFR A431 cells.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
epidermal growth factor receptor Hs Inhibitor Inhibition - - - 1
⤷ [1]