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Details

Stereochemistry ACHIRAL
Molecular Formula C25H27ClN6O3
Molecular Weight 494.973
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WZ-4002

SMILES

COC1=C(NC2=NC=C(Cl)C(OC3=CC=CC(NC(=O)C=C)=C3)=N2)C=CC(=C1)N4CCN(C)CC4

InChI

InChIKey=ITTRLTNMFYIYPA-UHFFFAOYSA-N
InChI=1S/C25H27ClN6O3/c1-4-23(33)28-17-6-5-7-19(14-17)35-24-20(26)16-27-25(30-24)29-21-9-8-18(15-22(21)34-3)32-12-10-31(2)11-13-32/h4-9,14-16H,1,10-13H2,2-3H3,(H,28,33)(H,27,29,30)

HIDE SMILES / InChI

Description

WZ4002 is a covalent pyrimidine inhibitor of EGFR, it demostrated the potency and relative selectivity for mutant EGFR forms. WZ4002 suppresses the growth of EGFR containing cell lines. It was effective in murine models of lung cancer driven by mutant EGFR.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Novel mutant-selective EGFR kinase inhibitors against EGFR T790M.
2009 Dec 24
Paracrine receptor activation by microenvironment triggers bypass survival signals and ALK inhibitor resistance in EML4-ALK lung cancer cells.
2012 Jul 1
Combined therapy with mutant-selective EGFR inhibitor and Met kinase inhibitor for overcoming erlotinib resistance in EGFR-mutant lung cancer.
2012 Oct
Ability of the Met kinase inhibitor crizotinib and new generation EGFR inhibitors to overcome resistance to EGFR inhibitors.
2013
Combined EGFR/MEK Inhibition Prevents the Emergence of Resistance in EGFR-Mutant Lung Cancer.
2015 Sep
Ibrutinib targets mutant-EGFR kinase with a distinct binding conformation.
2016 Oct 25
Patents

Patents

WO2010129053A2
1
WO2016191471A1
1

Sample Use Guides

In Vivo Use Guide
mouse lung cancer models : WZ4002 at 25mg/kg gavage daily
Route of Administration: Oral
In Vitro Use Guide
WZ4002 suppresses the growth of mutant EGFR T790M containing cell lines (IC50 values are in nanomolar range) and inhibit EGFR phosphorylation (0.1-1 uM)
Name Type Language
WZ-4002
Common Name English
N-(3-((5-CHLORO-2-((2-METHOXY-4-(4-METHYL-1-PIPERAZINYL)PHENYL)AMINO)-4-PYRIMIDINYL)OXY)PHENYL)-2-PROPENAMIDE
Systematic Name English
2-PROPENAMIDE, N-(3-((5-CHLORO-2-((2-METHOXY-4-(4-METHYL-1-PIPERAZINYL)PHENYL)AMINO)-4-PYRIMIDINYL)OXY)PHENYL)-
Systematic Name English
WZ4002
Code English
Code System Code Type Description
CAS
1213269-23-8
Created by admin on Sat Dec 16 06:40:07 UTC 2023 , Edited by admin on Sat Dec 16 06:40:07 UTC 2023
PRIMARY
FDA UNII
6BQ432Z61M
Created by admin on Sat Dec 16 06:40:07 UTC 2023 , Edited by admin on Sat Dec 16 06:40:07 UTC 2023
PRIMARY
PUBCHEM
44607530
Created by admin on Sat Dec 16 06:40:07 UTC 2023 , Edited by admin on Sat Dec 16 06:40:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID30153230
Created by admin on Sat Dec 16 06:40:07 UTC 2023 , Edited by admin on Sat Dec 16 06:40:07 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of WZ-4002
NIH
NCATS
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