NAV

Pelitinib

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

Identification

Generic Name
Pelitinib
DrugBank Accession Number
DB05524
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 467.93
Monoisotopic: 467.1524309
Chemical Formula
C24H23ClFN5O2
Synonyms
  • (2E)-N-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide
  • Pelitinib
External IDs
  • EKB-569
  • WAY-EKB-569
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Pelitinib is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Pelitinib is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Pelitinib is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Pelitinib is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Pelitinib is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
X5DWL380Z6
CAS number
257933-82-7
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

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. [Article]
  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. [Article]
ChemSpider
4949255
BindingDB
31090
ChEBI
38927
ChEMBL
CHEMBL607707
ZINC
ZINC000000602803
PDBe Ligand
93J
PDB Entries
5vcw / 7axm

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentColon Neoplasm / Colorectal Neoplasms / Rectal Neoplasms1
2CompletedTreatmentLung Neoplasm / Non-Small Cell Lung Carcinoma1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1

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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-b2775383252ca0967d4e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0002900000-aa0957347dc0865bb988
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-0009500000-b69f771030082afa8791
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pxr-0009700000-807d8d7b3ad5294ee326
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05ot-9017300000-93eb7c785dec7d4aec50
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00o3-5009400000-72db0eade853fb9ed4c0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Epidermal growth factor receptor
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. [Article]

Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51