crizotinib

Also known as (R)-crizotinib, PF 2341066, PF-02341066, PF-2341066, PF2341066, Xalkori®

Crizotinib, sold under the brand name Xalkori among others, is an anti-cancer medication used for the treatment of non-small cell lung carcinoma (NSCLC). Crizotinib inhibits the c-Met/Hepatocyte growth factor receptor (HGFR) tyrosine kinase, which is involved in the oncogenesis of a number of other histological forms of malignant neoplasms. It also acts as an ALK (anaplastic lymphoma kinase) and ROS1 (c-ros oncogene 1) inhibitor.

Chemical data

Formula: C21H22Cl2FN5O
Molecular weight: 450.3 g/mol
IUPAC name: 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine
SMILES: C[C@H](C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
InChIKey: KTEIFNKAUNYNJU-GFCCVEGCSA-N
XLogP: 3.7
Polar surface area: 78 Å²
H-bond donors: 2
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2011
Admin. routes: oral
Indications: glioblastoma multiforme, non-small cell lung carcinoma, neoplasm, papillary renal cell carcinoma

via ChEMBL · EBI

Research

3,920 papers

Brigatinib Versus Crizotinib in ALK Inhibitor-Naive Advanced ALK-Positive NSCLC: Final Results of Phase 3 ALTA-1L Trial.Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer · 2021
Crizotinib versus chemotherapy in advanced ALK-positive lung cancer.The New England journal of medicine · 2013
Crizotinib.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 2018
Spectrum of Mechanisms of Resistance to Crizotinib and Lorlatinib in ROS1 Fusion-Positive Lung Cancer.Clinical cancer research : an official journal of the American Association for Cancer Research · 2021
Inhibition of PRKAA/AMPK (Ser485/491) phosphorylation by crizotinib induces cardiotoxicity via perturbing autophagosome-lysosome fusion.Autophagy · 2024

via PubMed

Wikidata facts

Mass: 449.119
Has use: medication

Show 8 more facts

chemical formula: C₂₁H₂₂Cl₂FN₅O
subject has role: protein kinase inhibitors
canonical SMILES: CC(C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
isomeric SMILES: C[C@H](C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
World Health Organisation international non-proprietary name: crizotinib
physically interacts with: MET proto-oncogene, receptor tyrosine kinase
Commons category: Crizotinib
significant drug interaction: tacrolimus

Sources (4)

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Encyclopedic overview

10 sections

Contents

Medical uses
Mechanism of action
Society and culture
Legal status
Research
Lung cancer
Lymphomas
Other cancers
References
External links

== Medical uses == Crizotinib is indicated for the treatment of metastatic non-small cell lung cancer (NSCLC) or relapsed or refractory, systemic anaplastic large cell lymphoma (ALCL) that is ALK-positive.

Excerpted from Wikipedia’s “crizotinib” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

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