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Crizotinib
- PF-02341066 - PF-2341066
- Optical Purity: Optically pure
- Soluble in DMSO
- MF: C21H22Cl2FN5O
- MW: 450.34
Description
Potent, selective and ATP-competitive inhibitor of c-Met/HGF receptor and the nucleophosmin-anaplastic lymphoma kinase (NPM-ALK), with IC50 values to be 4 and 25 nM for c-Met and ALK respectively. (R)-Crizotinib is superior to standard chemotherapy in patients with previously treated, advanced non-smal-cell lung cancer with ALK rearrangement.
Notably, (S)-Crizotinib (Axon 2296) was recently found to potently inhibit the MTH1 phosphatase enzyme, whereas the (R) enantiomer is inactive (IC50 values of 72 nM and 1375 nM resp.).
More Information
| Parent CAS No. | 877399-52-5 |
|---|---|
| Chemical Name | (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine |
| extra_info | . |
| SMILES | C1C(Cl)=C([C@H](OC2C=C(C3C=NN(C4CCNCC4)C=3)C=NC=2N)C)C(Cl)=C(F)C=1 |&1:4,r| |
| MFCD | N.A. |
| 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 |
| InChiKey | KTEIFNKAUNYNJU-GFCCVEGCSA-N |
| CID | 11626560 |
| Short Description | MET/ALK inhibitor |
References
- A.T. Shaw et al. Crizotinib versus chemotherapy in advanced ALK-positive lung cancer. N. Engl. J. Med. 2013, 368, 2385-2394.
- HY Zou et al. An Orally Available Small-Molecule Inhibitor of c-Met, PF-2341066, Exhibits Cytoreductive Antitumor Efficacy through Antiproliferative and Antiangiogenic Mechanisms. Cancer Res. 2007, 67, 4408.
- SH Ou et al. Activity of Crizotinib (PF02341066), a Dual Mesenchymal-Epithelial Transition (MET) and Anaplastic Lymphoma Kinase (ALK) Inhibitor, in a Non-small Cell Lung Cancer Patient with De Novo MET Amplification. J. Thor. Oncol. 2011, 6(5), 942-946.
- K.V. Huber et al. Stereospecific targeting of MTH1 by (S)-crizotinib as an anticancer strategy. Nature. 2014, doi: 10.1038/nature13194. [Epub ahead of print]
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