Canertinib
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
- 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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- Pharmacodynamics
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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetaminophen The serum concentration of Acetaminophen can be increased when it is combined with Canertinib. Ambroxol The risk or severity of methemoglobinemia can be increased when Canertinib is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Canertinib is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Canertinib is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Canertinib is combined with Benzyl alcohol. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Canertinib dihydrochloride ICJ93X8X90 289499-45-2 JZZFDCXSFTVOJY-UHFFFAOYSA-N
Categories
- Drug Categories
- Acids, Acyclic
- Anesthetics
- Antineoplastic Agents
- Cardiotonic Agents
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Compounds used in a research, industrial, or household setting
- Oxazines
- Peripheral Nervous System Agents
- Protective Agents
- Sensory System Agents
- Tyrosine Kinase Inhibitors
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Breast Neoplasms 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 splash10-0019-0100900000-598c2693e0114d45e70a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-1004900000-eb643a83c3fda8b1685b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001s-0204900000-5ac6c29f55b9e8ea4c3c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-015l-3006900000-b54a56ecbc16cc31bf76 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udl-1305900000-3ad4bf46628010c60a37 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-5009400000-b02e67aadf0f532a8dd6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.27155 predictedDeepCCS 1.0 (2019) [M+H]+ 211.62956 predictedDeepCCS 1.0 (2019) [M+Na]+ 217.80986 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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