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PZ0191

Sigma-Aldrich

Crizotinib

≥98% (HPLC)

Synonym(s):

(R)-3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine, PF 2341066, PF-02341066, PF02341066, Xalkori

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About This Item

Empirical Formula (Hill Notation):
C21H22Cl2FN5O
CAS Number:
877399-52-5
Molecular Weight:
450.34
MDL number:
MFCD12407409
UNSPSC Code:
12352200
PubChem Substance ID:
329823765
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

storage temp.

room temp

SMILES string

C[C@@H](Oc1cc(cnc1N)-c2cnn(c2)C3CCNCC3)c4c(Cl)ccc(F)c4Cl

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

InChI key

KTEIFNKAUNYNJU-GFCCVEGCSA-N

Gene Information

human ... ALK(238), MET(4233)

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antibody form

purified antibody

antibody form

purified antibody

antibody form

purified antibody

antibody form

purified antibody

clone

52H11, recombinant monoclonal

clone

3F5, recombinant monoclonal

clone

1G3, recombinant monoclonal

clone

2K14, recombinant monoclonal

biological source

rabbit

biological source

rabbit

biological source

rabbit

biological source

rabbit

conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

conjugate

unconjugated

species reactivity

human

species reactivity

human, rat

species reactivity

human, rat, mouse

species reactivity

human

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Application

Crizotinib has been used:
  • to investigate its effects on hepatocyte growth factor receptor (c-Met) expression, proliferation and apoptosis[1]
  • to block neurotrophic tyrosine kinase receptor type 1 (NTRK1) activity in epithelial cells[2]
  • to restore sensitivity to erlotinib[3]

Biochem/physiol Actions

ATP-competitive c-MET / ALK Inhibitor
Crizotinib (PF-02341066) is an ATP-competitive inhibitor of the receptor tyrosine kinases (RTKs) c-Met (hepatocyte growth factor receptor) and anaplastic lymphoma kinase (ALK). Crizotinib is a highly specific inhibitor of c-Met and ALK among > 120 different RTKs surveyed. Crizotinib was approved for treatment of a subtype of nonsmall-cell lung cancer (NSCLC) with ALK fusion mutations.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2 - Muta. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
034M4739V
091M4718V

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Registered report: Widespread potential for growth factor-driven resistance to anticancer kinase inhibitors
Greenfield E, et al.
eLife, 3, e04037-e04037 (2014)
Shota Yamamoto et al.
Radiology, 272(2), 568-576 (2014-06-03)
To present a radiogenomic computed tomographic (CT) characterization of anaplastic lymphoma kinase (ALK)-rearranged non-small cell lung cancer (NSCLC) (ALK+). In this HIPAA-compliant institutional review board-approved retrospective study, CT studies, ALK status, and clinical-pathologic data in 172 patients with NSCLC from
PF-2341066 combined with celecoxib promotes apoptosis and inhibits proliferation in human cholangiocarcinoma QBC939 cells
Chen C, et al.
Experimental and Therapeutic Medicine, 15(5), 4543-4549 (2018)
Neurotrophic tyrosine kinase receptor 1 is a direct transcriptional and epigenetic target of IL-13 involved in allergic inflammation
Rochman M, et al.
Mucosal Immunology, 8(4), 785-785 (2015)
Damini Chand et al.
Disease models & mechanisms, 6(2), 373-382 (2012-10-30)
Neuroblastoma is a childhood extracranial solid tumour that is associated with a number of genetic changes. Included in these genetic alterations are mutations in the kinase domain of the anaplastic lymphoma kinase (ALK) receptor tyrosine kinase (RTK), which have been
View All Related Papers

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