Identification
- Generic Name
- Canertinib
- DrugBank Accession Number
- DB05424
- Background
Canertinib is a pan-erbB tyrosine kinase inhibitor which work against esophageal squamous cell carcinoma in vitro and in vivo. Canertinib treatment significantly affects tumour metabolism, proliferation and hypoxia as determined by PET.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Canertinib (DB05424)
- Weight
- Average: 485.938
Monoisotopic: 485.162995603 - Chemical Formula
- C24H25ClFN5O3
- Synonyms
- Canertinib
- External IDs
- PD-183805
Pharmacology
- Indication
Investigated for use/treatment in breast cancer and lung cancer.
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Not Available
- Mechanism of action
CI-1033 effectively inhibits the growth of esophageal squamous cell carcinoma which co-expresses both EGFR and HER2 with the inhibition of phosphorylation of both MAPK and AKT. Some studies suggest that CI-1033 holds significant clinical potential in esophageal cancer.
Target Actions Organism UEpidermal growth factor receptor Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The therapeutic efficacy of Abaloparatide can be decreased when used in combination with Canertinib. Acetaminophen The serum concentration of Acetaminophen can be increased when it is combined with Canertinib. Carbimazole The therapeutic efficacy of Carbimazole can be decreased when used in combination with Canertinib. Darbepoetin alfa The risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Canertinib. Erythropoietin The risk or severity of Thrombosis can be increased when Erythropoietin is combined with Canertinib. Follitropin The therapeutic efficacy of Follitropin can be decreased when used in combination with Canertinib. Levothyroxine The therapeutic efficacy of Levothyroxine can be decreased when used in combination with Canertinib. Liothyronine The therapeutic efficacy of Liothyronine can be decreased when used in combination with Canertinib. Liotrix The therapeutic efficacy of Liotrix can be decreased when used in combination with Canertinib. Methimazole The therapeutic efficacy of Methimazole can be decreased when used in combination with Canertinib. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Canertinib dihydrochloride ICJ93X8X90 289499-45-2 JZZFDCXSFTVOJY-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Benzodiazines
- Direct Parent
- Quinazolinamines
- Alternative Parents
- Aniline and substituted anilines / N-arylamides / Alkyl aryl ethers / Aminopyrimidines and derivatives / Chlorobenzenes / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Imidolactams / Morpholines show 15 more
- Substituents
- Acrylic acid or derivatives / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide show 33 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, monochlorobenzenes, quinazolines, morpholines (CHEBI:61399)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- C78W1K5ASF
- CAS number
- 267243-28-7
- InChI Key
- OMZCMEYTWSXEPZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29)
- IUPAC Name
- N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide
- SMILES
- FC1=C(Cl)C=C(NC2=NC=NC3=CC(OCCCN4CCOCC4)=C(NC(=O)C=C)C=C23)C=C1
References
- General References
- Simon GR, Garrett CR, Olson SC, Langevin M, Eiseman IA, Mahany JJ, Williams CC, Lush R, Daud A, Munster P, Chiappori A, Fishman M, Bepler G, Lenehan PF, Sullivan DM: Increased bioavailability of intravenous versus oral CI-1033, a pan erbB tyrosine kinase inhibitor: results of a phase I pharmacokinetic study. Clin Cancer Res. 2006 Aug 1;12(15):4645-51. [Article]
- Sequist LV: Second-generation epidermal growth factor receptor tyrosine kinase inhibitors in non-small cell lung cancer. Oncologist. 2007 Mar;12(3):325-30. [Article]
- External Links
- PubChem Compound
- 156414
- PubChem Substance
- 175427000
- ChemSpider
- 137741
- BindingDB
- 4779
- ChEBI
- 61399
- ChEMBL
- CHEMBL31965
- ZINC
- ZINC000027439698
- Wikipedia
- Canertinib
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Neoplasms, Breast 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
Property Value Source Water Solubility 0.0155 mg/mL ALOGPS logP 4.09 ALOGPS logP 3.9 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 12.54 ChemAxon pKa (Strongest Basic) 6.87 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 88.61 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 130.55 m3·mol-1 ChemAxon Polarizability 50.36 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9917 Blood Brain Barrier + 0.9577 Caco-2 permeable - 0.5685 P-glycoprotein substrate Substrate 0.6999 P-glycoprotein inhibitor I Inhibitor 0.9152 P-glycoprotein inhibitor II Inhibitor 0.9592 Renal organic cation transporter Inhibitor 0.5 CYP450 2C9 substrate Non-substrate 0.8114 CYP450 2D6 substrate Non-substrate 0.7455 CYP450 3A4 substrate Substrate 0.6732 CYP450 1A2 substrate Non-inhibitor 0.5366 CYP450 2C9 inhibitor Inhibitor 0.5958 CYP450 2D6 inhibitor Non-inhibitor 0.8724 CYP450 2C19 inhibitor Inhibitor 0.5504 CYP450 3A4 inhibitor Inhibitor 0.827 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8911 Ames test Non AMES toxic 0.5465 Carcinogenicity Non-carcinogens 0.8916 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7549 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5387 hERG inhibition (predictor II) Inhibitor 0.8273
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
Drug created at November 18, 2007 18:24 / Updated at February 21, 2021 18:51