Drug Details

General Information of the Drug (ID: DR2569)
Name
Crizotinib
Synonyms
Crizotinib; 877399-52-5; Xalkori; PF-02341066; (R)-crizotinib; PF-2341066; PF 2341066; Crizotinib (PF-02341066); 3-[(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1H-pyrazol-4-yl]-2-pyridinamine; PF 02341066; (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine; UNII-53AH36668S; PF2341066; CHEMBL601719; Crizotinib (PF-2341066); CHEBI:64310; 877399-52-5 (free base); 53AH36668S; 3-[(1R)-1-(2,6-DICHLORO-3-FLUOROPHENYL)ETHOXY]-5-[1-(4-PIPERIDINYL)-1H-PYRAZOL-4-YL]PYRIDIN-2-AMINE; 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine; 3-[(1r)-1-(2,6-Dichloro-3-Fluorophenyl)ethoxy]-5-(1-Piperidin-4-Yl-1h-Pyrazol-4-Yl)pyridin-2-Amine; (R)-3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine; Xalkori (TN); C21H22Cl2FN5O; Crizotinib [USAN:INN]; crizotinibum; VGH; PubChem19322; PF02341066; SCHEMBL93829; PF-2341066,Crizotinib; cc-190; Crizotinib (JAN/USAN/INN); PF-2341066(Crizotinib); GTPL4903; QCR-32; Crizotinib, >=98% (HPLC); PF-2341066 (Crizotinib); PF-2341066 - Crizotinib; AOB2688; EX-A096; SYN1139; PF-02341066 (Crizotinib); BCPP000116; DTXSID701009329; 3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine; AMY10313; ABP000131; ANW-47749; BDBM50306682; MFCD12407409; NSC749005; NSC749769; NSC800080; ZINC35902489; AKOS015901233; AKOS015995207; CCG-264803; DB08865; GS-6178; NSC 756645; NSC-749005; NSC-749769; NSC-800080; PB11015; NCGC00250400-01; NCGC00250400-02; NCGC00250400-09; NCGC00250400-12; 2-Pyridinamine, 3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(4-piperidinyl)-1H-pyrazol-4-yl)-; HY-50878; AB0027203; BB 0261738; SW202555-3; W9013; D09731; Q-3209; 399P525; J-510370; Q5186964; BRD-K78431006-001-01-1; BRD-K78431006-001-03-7; 877399-52-5, 877399-53-6 (acetate); 3-(2,6-dichloro-3-fluorobenzyloxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine; (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-am ine; 3-(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy-5-1-(4-piperidinyl)-1H-pyrazol-4-yl-2-Pyridinamine; 3-[(R)-1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine
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Molecular Type
Small molecule
Disease Lung cancer [ICD-11: 2C25] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C21H22Cl2FN5O
PubChem CID
11626560
Canonical SMILES
CC(C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
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
InChIKey
KTEIFNKAUNYNJU-GFCCVEGCSA-N
CAS Number
CAS 877399-52-5
ChEBI ID
CHEBI:64310
TTD Drug ID
D03ZBT
DrugBank ID
DB08865
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Norcantharidin      Epicauta pensylvanica     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation MET  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation mTOR  Molecule Info 
Pathway MAP
                    In-vitro Model MHCC97-H CVCL_4972 Adult hepatocellular carcinoma Homo sapiens
Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    In-vivo Model For a xenograft model, 2*106 human HepG2 cells were injected subcutaneously into the right flanks of the mice into the right flanks of the mice.
                    Experimental
                    Result(s)		 Cytotoxic autophagy resulting from inhibition of c-Met/mTOR signaling may be achieved in HCC by combined NCTD and crizotinib administration.
Target and Pathway
Target(s) ALK tyrosine kinase receptor (ALK)  Molecule Info  [3]
Proto-oncogene c-Met (MET)  Molecule Info  [3]
Proto-oncogene c-Ros (ROS1)  Molecule Info  [3]
KEGG Pathway Ras signaling pathway Click to Show/Hide
2 Rap1 signaling pathway
3 Cytokine-cytokine receptor interaction
4 Endocytosis
5 PI3K-Akt signaling pathway
6 Axon guidance
7 Focal adhesion
8 Adherens junction
9 Bacterial invasion of epithelial cells
10 Epithelial cell signaling in Helicobacter pylori infection
11 Malaria
12 Pathways in cancer
13 Transcriptional misregulation in cancer
14 Proteoglycans in cancer
15 MicroRNAs in cancer
16 Renal cell carcinoma
17 Melanoma
18 Central carbon metabolism in cancer
19 Non-small cell lung cancer
Pathway Interaction Database Signaling events mediated by Hepatocyte Growth Factor Receptor (c-Met) Click to Show/Hide
2 Arf6 signaling events
3 Signaling events mediated by TCPTP
4 Posttranslational regulation of adherens junction stability and dissassembly
5 Direct p53 effectors
6 Syndecan-1-mediated signaling events
7 Stabilization and expansion of the E-cadherin adherens junction
8 a6b1 and a6b4 Integrin signaling
9 FGF signaling pathway
10 Regulation of retinoblastoma protein
Reactome Sema4D mediated inhibition of cell attachment and migration Click to Show/Hide
WikiPathways TGF beta Signaling Pathway Click to Show/Hide
2 Signaling of Hepatocyte Growth Factor Receptor
3 Focal Adhesion
4 Extracellular vesicle-mediated signaling in recipient cells
5 Signaling Pathways in Glioblastoma
6 miR-targeted genes in squamous cell - TarBase
7 miR-targeted genes in muscle cell - TarBase
8 miR-targeted genes in lymphocytes - TarBase
9 miR-targeted genes in epithelium - TarBase
10 Semaphorin interactions
11 Spinal Cord Injury
12 Differentiation Pathway
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4903).
Reference 2 Norcantharidin alone or in combination with crizotinib induces autophagic cell death in hepatocellular carcinoma by repressing c-Met-mTOR signaling. Oncotarget. 2017 Dec 4;8(70):114945-114955.
Reference 3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
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