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Details

Stereochemistry ACHIRAL
Molecular Formula C24H23ClFN5O2
Molecular Weight 467.923
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PELITINIB

SMILES

CCOC1=C(NC(=O)\C=C\CN(C)C)C=C2C(=C1)N=CC(C#N)=C2NC3=CC(Cl)=C(F)C=C3

InChI

InChIKey=WVUNYSQLFKLYNI-AATRIKPKSA-N
InChI=1S/C24H23ClFN5O2/c1-4-33-22-12-20-17(11-21(22)30-23(32)6-5-9-31(2)3)24(15(13-27)14-28-20)29-16-7-8-19(26)18(25)10-16/h5-8,10-12,14H,4,9H2,1-3H3,(H,28,29)(H,30,32)/b6-5+

HIDE SMILES / InChI

Molecular Formula C24H23ClFN5O2
Molecular Weight 467.923
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800014700 | http://www.pharmacodia.com/yaodu/html/v1/chemicals/417346143631ba772ccbbb20c6c4151b.html | https://www.wikigenes.org/e/chem/e/6445562.html | https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=352165

Pelitinib (EKB-569) is a 3-cyanoquinoline pan-ErbB tyrosine kinase inhibitor with potential antineoplastic activity. Pelitinib irreversibly binds covalently to epidermal growth factor receptors, thereby inhibiting receptor phosphorylation and signal transduction and resulting in apoptosis and suppression of proliferation in tumor cells that overexpress these receptors. Pelitinib had been in phase II clinical trials for the treatment of non-small cell lung cancer and colorectal cancer. Treatment-emergent adverse events were diarrhea, abdominal pain, gastrointestinal carcinoma, intestinal obstruction and vomiting.

Originator

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/12502359 16 Oct 2009 Wyeth has been acquired by Pfizer. # Wyeth Pharmaceuticals

Approval Year

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Irreversible EGFR inhibitor EKB-569 targets low-LET γ-radiation-triggered rel orchestration and potentiates cell death in squamous cell carcinoma.
2011
Cysteine mapping in conformationally distinct kinase nucleotide binding sites: application to the design of selective covalent inhibitors.
2011 Mar 10
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The recommended dose of EKB-569 is 25 mg/day when combined with FOLFIRI. https://www.ncbi.nlm.nih.gov/pubmed/18172273
The maximum tolerated dose of EKB-569 is 75 mg once-daily.
Route of Administration: Oral
Pelitinib has been found to exert a potent anti-proliferative activity against tumor cells overexpressing EGF-R, including NHEK, A431 and MDA-468 cells, with IC50 values of 61 nM, 125 nM and 260 nM respectively; while it has also been found to potently inhibit EGF-induced phosphorylated EGF-R (pEGF-R) in A431 and NHEK cells with IC50 values ranging from 20 nM to 80 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:28:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:46 GMT 2023
Record UNII
X5DWL380Z6
Record Status Validated (UNII)
Record Version
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Name Type Language
PELITINIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
EKB-569
Code English
pelitinib [INN]
Common Name English
WAY-EKB-569
Code English
Pelitinib [WHO-DD]
Common Name English
2-BUTENAMIDE, N-(4-((3-CHLORO-4-FLUOROPHENYL)AMINO)-3-CYANO-7-ETHOXY-6-QUINOLINYL)-4-(DIMETHYLAMINO)-, (2E)-
Systematic Name English
(2E)-N-(-((3-CHLORO-4-FLUOROPHENYL)AMINO)3-CYANO-7-ETHOXYQUINOLIN-6-YL)-4-(DIMETHYLAMINO)BUT-2-ENAMIDE
Systematic Name English
PELITINIB [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2167
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
NCI_THESAURUS C129825
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
Code System Code Type Description
USAN
PP-45
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
SMS_ID
100000151604
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
CHEBI
38927
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
PUBCHEM
6445562
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL607707
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID90870294
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
FDA UNII
X5DWL380Z6
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
CAS
257933-82-7
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
EVMPD
SUB125846
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
NCI_THESAURUS
C2713
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
DRUG BANK
DB05524
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
INN
8462
Created by admin on Fri Dec 15 15:28:46 GMT 2023 , Edited by admin on Fri Dec 15 15:28:46 GMT 2023
PRIMARY
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