Pelitinib

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Pelitinib
Accession Number
DB05524
Type
Small Molecule
Groups
Investigational
Description

Pelitinib (EKB-569) is a potent, low molecular weight, selective, and irreversible inhibitor of epidermal growth factor receptor (EGFR) that is being developed as an anticancer agent.

Structure
Thumb
Synonyms
  • (2E)-N-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide
External IDs
EKB-569 / WAY-EKB-569
Categories
UNII
X5DWL380Z6
CAS number
257933-82-7
Weight
Average: 467.93
Monoisotopic: 467.1524309
Chemical Formula
C24H23ClFN5O2
InChI Key
WVUNYSQLFKLYNI-AATRIKPKSA-N
InChI
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+
IUPAC Name
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-3-cyano-7-ethoxyquinolin-6-yl}-4-(dimethylamino)but-2-enamide
SMILES
CCOC1=CC2=C(C=C1NC(=O)\C=C\CN(C)C)C(NC1=CC(Cl)=C(F)C=C1)=C(C=N2)C#N

Pharmacology

Indication

Investigated for use/treatment in colorectal cancer and lung cancer.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEpidermal growth factor receptorNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Yoshimura N, Kudoh S, Kimura T, Mitsuoka S, Matsuura K, Hirata K, Matsui K, Negoro S, Nakagawa K, Fukuoka M: EKB-569, a new irreversible epidermal growth factor receptor tyrosine kinase inhibitor, with clinical activity in patients with non-small cell lung cancer with acquired resistance to gefitinib. Lung Cancer. 2006 Mar;51(3):363-8. Epub 2005 Dec 20. [PubMed:16364494]
  2. Palayekar MJ, Herzog TJ: The emerging role of epidermal growth factor receptor inhibitors in ovarian cancer. Int J Gynecol Cancer. 2008 Sep-Oct;18(5):879-90. Epub 2007 Dec 5. [PubMed:18053062]
External Links
ChemSpider
4949255
BindingDB
31090
ChEBI
38927
ChEMBL
CHEMBL607707
HET
93J
PDB Entries
5vcw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentColonic Neoplasms / Neoplasms, Colorectal / Rectal Neoplasms1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Neoplasms, Lung / Non-Small Cell Lung Carcinoma (NSCLC)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0078 mg/mLALOGPS
logP4.56ALOGPS
logP4.18ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.28 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity129.11 m3·mol-1ChemAxon
Polarizability47.61 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TG...
Gene Name
EGFR
Uniprot ID
P00533
Uniprot Name
Epidermal growth factor receptor
Molecular Weight
134276.185 Da
References
  1. Yoshimura N, Kudoh S, Kimura T, Mitsuoka S, Matsuura K, Hirata K, Matsui K, Negoro S, Nakagawa K, Fukuoka M: EKB-569, a new irreversible epidermal growth factor receptor tyrosine kinase inhibitor, with clinical activity in patients with non-small cell lung cancer with acquired resistance to gefitinib. Lung Cancer. 2006 Mar;51(3):363-8. Epub 2005 Dec 20. [PubMed:16364494]

Drug created on November 18, 2007 11:25 / Updated on June 04, 2019 06:17