Crizotinib
Identification
- Name
- Crizotinib
- Accession Number
- DB08865
- Description
Crizotinib an inhibitor of receptor tyrosine kinase for the treatment of non-small cell lung cancer (NSCLC). Verification of the presence of ALK fusion gene is done by Abbott Molecular's Vysis ALK Break Apart FISH Probe Kit. This verification is used to select for patients suitable for treatment. FDA approved in August 26, 2011.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Crizotinib (DB08865)
- Weight
- Average: 450.337
Monoisotopic: 449.11854397 - Chemical Formula
- C21H22Cl2FN5O
- Synonyms
- (R)-crizotinib
- Crizotinib
- Crizotinibum
- External IDs
- 1066
- PF 02341066
- PF 2341066
- PF-02341066
- PF-2341066
Pharmacology
- Indication
Crizotinib is used for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) that is anaplastic-lymphoma kinase (ALK)-positive as detected by a FDA-approved test.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Crizotinib is a tyrosine kinase receptor inhibitor. More specifically, it inhibits anaplastic lymphoma kinase (ALK), hepatocyte growth factor receptor (HGFR, c-MET), and Recepteur d'Origine Nantais (RON). Abnormalities in the ALK gene caused by mutations or translocations may lead to expression of oncogenic fusion proteins. In patients with NSCLC, they have the EML4-ALK gene. Crizotinib inhibits ALK tyrosine kinase which ultimately results in decreased proliferation of cells that carry the genetic mutation and tumour survivability.
Target Actions Organism AALK tyrosine kinase receptor inhibitorHumans AHepatocyte growth factor receptor inhibitorHumans - Absorption
The peak serum concentration was reached in 4 to 6 hours following an oral single-dose administration. Steady state was reached within 15 days when a dose of 250 mg twice daily was administered. The mean absolute bioavailability was 43% (range of 32% to 66%) following a single 250 mg oral dose. When taken with high-fat meal, AUC and Cmax were reduced.
- Volume of distribution
Mean volume of distribution (Vss) is 1772 L following intravenous administration of a 50 mg dose. This high volume of distribution suggest extensive distribution into tissue from plasma.
- Protein binding
Crizotinib is 91% bound to plasma protein. This is not affected by drug concentration.
- Metabolism
Crizotinib is metabolized by CYP3A4 and CYP3A5 in which these enzymes mediates the O-dealkylation of the drug.
- Route of elimination
Following the administration of a single 250 mg radiolabeled crizotinib dose to healthy subjects, 63% and 22% of the administered dose was recovered in feces and urine, respectively. Unchanged crizotinib represented approximately 53% and 2.3% of the administered dose in feces and urine, respectively.
- Half-life
Plasma terminal half-life, patients = 42 hours
- Clearance
The mean apparent clearance (CL/F) of crizotinib was lower at steady state (60 L/hr) after 250 mg twice daily than that after a single 250 mg oral dose (100 L/hr), which was likely due to autoinhibition of CYP3A by crizotinib after multiple dosing.
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAbaloparatide The therapeutic efficacy of Abaloparatide can be decreased when used in combination with Crizotinib. Abametapir The serum concentration of Crizotinib can be increased when it is combined with Abametapir. Abatacept The metabolism of Crizotinib can be increased when combined with Abatacept. Abiraterone The metabolism of Abiraterone can be decreased when combined with Crizotinib. Acalabrutinib The metabolism of Crizotinib can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of QTc prolongation can be increased when Acebutolol is combined with Crizotinib. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Crizotinib. Acetaminophen The metabolism of Acetaminophen can be increased when combined with Crizotinib. Acetazolamide The metabolism of Crizotinib can be decreased when combined with Acetazolamide. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Crizotinib. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum levels of crizotinib.
- Avoid St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce serum levels of crizotinib.
- Take with or without food. High-fat food decreases drug absorption, but not to a clinically significant extent.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataXalkori Capsule 250 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 2011-08-26 Not applicable US 
Xalkori Capsule 200 mg Oral Pfizer 2012-10-23 Not applicable EU 
Xalkori Capsule Oral Pfizer Canada Ulc 2012-05-10 Not applicable Canada 
Xalkori Capsule 250 mg Oral Pfizer 2012-10-23 Not applicable EU Xalkori Capsule 200 mg Oral Pfizer 2012-10-23 Not applicable EU Xalkori Capsule 200 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 2011-08-26 Not applicable US Xalkori Capsule 250 mg Oral Pfizer 2012-10-23 Not applicable EU Xalkori Capsule Oral Pfizer Canada Ulc 2012-05-10 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L01XE16 — Crizotinib
- Drug Categories
- Amines
- Aminopyridines
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Bradycardia-Causing Agents
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Kinase Inhibitor
- Moderate Risk QTc-Prolonging Agents
- OCT2 Inhibitors
- Organic Cation Transporter 1 Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- P-glycoprotein substrates with narrow therapeutic index
- Piperidines
- Protein Kinase Inhibitors
- Pyridines
- QTc Prolonging Agents
- Receptor Tyrosine Kinase Inhibitors
- Tyrosine Kinase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrazolylpyridines. These are compounds containing a pyrazolylpyridine skeleton, which consists of a pyrazole linked (not fused) to a pyridine by a bond.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pyrazolylpyridines
- Direct Parent
- Pyrazolylpyridines
- Alternative Parents
- Dichlorobenzenes / Alkyl aryl ethers / Aminopyridines and derivatives / Fluorobenzenes / Piperidines / Aryl chlorides / Aryl fluorides / Imidolactams / Pyrazoles / Heteroaromatic compounds show 7 more
- Substituents
- 1,3-dichlorobenzene / 3-pyrazolylpyridine / Alkyl aryl ether / Amine / Aminopyridine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle show 23 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine (CHEBI:64310)
Chemical Identifiers
- UNII
- 53AH36668S
- CAS number
- 877399-52-5
- InChI Key
- KTEIFNKAUNYNJU-GFCCVEGCSA-N
- InChI
- InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
- IUPAC Name
- 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine
- SMILES
- C[[email protected]@H](OC1=CC(=CN=C1N)C1=CN(N=C1)C1CCNCC1)C1=C(Cl)C=CC(F)=C1Cl
References
- General References
- Timm A, Kolesar JM: Crizotinib for the treatment of non-small-cell lung cancer. Am J Health Syst Pharm. 2013 Jun 1;70(11):943-7. doi: 10.2146/ajhp120261. [PubMed:23686600]
- Forde PM, Rudin CM: Crizotinib in the treatment of non-small-cell lung cancer. Expert Opin Pharmacother. 2012 Jun;13(8):1195-201. doi: 10.1517/14656566.2012.688029. [PubMed:22594847]
- External Links
- KEGG Drug
- D09731
- PubChem Compound
- 11626560
- PubChem Substance
- 310264901
- ChemSpider
- 9801307
- BindingDB
- 50306682
- 1148495
- ChEBI
- 64310
- ChEMBL
- CHEMBL601719
- ZINC
- ZINC000035902489
- PharmGKB
- PA165946122
- PDBe Ligand
- VGH
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Crizotinib
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- PDB Entries
- 2wgj / 2xp2 / 2yfx / 3zbf / 4anq / 4ans / 4c9w / 5aaa / 5aab / 5aac … show 1 more
- FDA label
- Download (279 KB)
- MSDS
- Download (105 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Recruiting Treatment ALK or ROS1-positive NSCLC 1 4 Recruiting Treatment ALK-Positive Anaplastic Large Cell Lymphoma 1 4 Withdrawn Treatment Systemic Anaplastic Large Cell Lymphoma / Systemic Anaplastic Large-Cell Lymphoma 1 3 Active Not Recruiting Treatment Advanced Malignancies / Carcinoma NOS / Lung Cancers / Non-Small Cell Lung Carcinoma (NSCLC) 1 3 Active Not Recruiting Treatment Anaplastic Lymphoma Kinase-positive Non-small Cell Lung Cancer 1 3 Active Not Recruiting Treatment Neoplasms 1 3 Active Not Recruiting Treatment Non-Small Cell Lung Carcinoma (NSCLC) 2 3 Completed Treatment Non-Small Cell Lung Carcinoma (NSCLC) 2 3 Recruiting Treatment ALK Gene Rearrangement / ALK Gene Translocation / ALK positive / Stage IB Non-Small Cell Lung Carcinoma AJCC v7 / Stage II Non-Small Cell Lung Cancer AJCC v7 / Stage IIA Non-Small Cell Lung Carcinoma AJCC v7 / Stage IIB Non-Small Cell Lung Carcinoma AJCC v7 / Stage IIIA Non-Small Cell Lung Cancer AJCC v7 1 3 Recruiting Treatment ALK-positive NSCLC 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Capsule Oral 200 mg/1 Capsule Oral 200 mg Capsule Oral 250 mg/1 Capsule Oral 250 mg Capsule 200 mg Capsule Oral Capsule 250 mg Capsule, coated Oral 200 mg Capsule, coated Oral 250 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataCA2517256 No 2013-04-30 2024-02-26 Canada CA2577937 No 2010-12-21 2025-08-15 Canada CA2578066 No 2011-10-11 2025-08-15 Canada CA2632286 No 2011-11-15 2026-11-23 Canada US7825137 No 2010-11-02 2027-05-12 US US7858643 No 2010-12-28 2029-10-08 US US7230098 No 2007-06-12 2025-08-26 US US8217057 No 2012-07-10 2029-11-06 US US8785632 No 2014-07-22 2025-03-01 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.83 MSDS - Predicted Properties
Property Value Source Water Solubility 0.00611 mg/mL ALOGPS logP 3.82 ALOGPS logP 3.57 ChemAxon logS -4.9 ALOGPS pKa (Strongest Basic) 10.12 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 77.99 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 128.43 m3·mol-1 ChemAxon Polarizability 45.44 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9721 Caco-2 permeable - 0.5672 P-glycoprotein substrate Substrate 0.6938 P-glycoprotein inhibitor I Non-inhibitor 0.6713 P-glycoprotein inhibitor II Inhibitor 0.7105 Renal organic cation transporter Inhibitor 0.5464 CYP450 2C9 substrate Non-substrate 0.7545 CYP450 2D6 substrate Non-substrate 0.7023 CYP450 3A4 substrate Substrate 0.6029 CYP450 1A2 substrate Inhibitor 0.6676 CYP450 2C9 inhibitor Inhibitor 0.5 CYP450 2D6 inhibitor Non-inhibitor 0.8662 CYP450 2C19 inhibitor Inhibitor 0.6237 CYP450 3A4 inhibitor Non-inhibitor 0.6301 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8676 Ames test Non AMES toxic 0.5981 Carcinogenicity Non-carcinogens 0.8018 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6581 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.643 hERG inhibition (predictor II) Inhibitor 0.7877
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 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-1693800000-fc52c38f3359a378554a
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transmembrane receptor protein tyrosine kinase activity
- Specific Function
- Neuronal orphan receptor tyrosine kinase that is essentially and transiently expressed in specific regions of the central and peripheral nervous systems and plays an important role in the genesis a...
- Gene Name
- ALK
- Uniprot ID
- Q9UM73
- Uniprot Name
- ALK tyrosine kinase receptor
- Molecular Weight
- 176440.535 Da
References
- Forde PM, Rudin CM: Crizotinib in the treatment of non-small-cell lung cancer. Expert Opin Pharmacother. 2012 Jun;13(8):1195-201. doi: 10.1517/14656566.2012.688029. [PubMed:22594847]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Protein tyrosine kinase activity
- Specific Function
- Receptor tyrosine kinase that transduces signals from the extracellular matrix into the cytoplasm by binding to hepatocyte growth factor/HGF ligand. Regulates many physiological processes including...
- Gene Name
- MET
- Uniprot ID
- P08581
- Uniprot Name
- Hepatocyte growth factor receptor
- Molecular Weight
- 155540.035 Da
References
- Forde PM, Rudin CM: Crizotinib in the treatment of non-small-cell lung cancer. Expert Opin Pharmacother. 2012 Jun;13(8):1195-201. doi: 10.1517/14656566.2012.688029. [PubMed:22594847]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Timm A, Kolesar JM: Crizotinib for the treatment of non-small-cell lung cancer. Am J Health Syst Pharm. 2013 Jun 1;70(11):943-7. doi: 10.2146/ajhp120261. [PubMed:23686600]
- Xalkori (Crizotinib) FDA Label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Timm A, Kolesar JM: Crizotinib for the treatment of non-small-cell lung cancer. Am J Health Syst Pharm. 2013 Jun 1;70(11):943-7. doi: 10.2146/ajhp120261. [PubMed:23686600]
- Xalkori (Crizotinib) FDA Label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Components:
| Name | UniProt ID |
|---|---|
| Cytochrome P450 3A4 | P08684 |
| Cytochrome P450 3A43 | Q9HB55 |
| Cytochrome P450 3A5 | P20815 |
| Cytochrome P450 3A7 | P24462 |
References
- Filppula AM, Neuvonen PJ, Backman JT: In vitro assessment of time-dependent inhibitory effects on CYP2C8 and CYP3A activity by fourteen protein kinase inhibitors. Drug Metab Dispos. 2014 Jul;42(7):1202-9. doi: 10.1124/dmd.114.057695. Epub 2014 Apr 8. [PubMed:24713129]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Timm A, Kolesar JM: Crizotinib for the treatment of non-small-cell lung cancer. Am J Health Syst Pharm. 2013 Jun 1;70(11):943-7. doi: 10.2146/ajhp120261. [PubMed:23686600]
Drug created on March 28, 2013 11:22 / Updated on October 21, 2020 01:55
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