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Merck

PZ0191

Crizotinib

≥98% (HPLC), c-Met (hepatocyte growth factor receptor) inhibitor, powder

Crizotinib

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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5 MG

€ 124,00

€ 124,00

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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

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Product Name

Crizotinib, ≥98% (HPLC)

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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This Item
PZ0195PZ0351PZ0357
Crizotinib ≥98% (HPLC)

Sigma-Aldrich

PZ0191

Crizotinib

CYP3cide ≥98% (HPLC)

Sigma-Aldrich

PZ0195

CYP3cide

PF-2545920 hydrochloride ≥97% (HPLC)

Sigma-Aldrich

PZ0351

PF-2545920 hydrochloride

PF-06412562 ≥98% (HPLC)

Sigma-Aldrich

PZ0357

PF-06412562

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

color

white to tan

color

white to beige

color

white to brown

color

white to beige

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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.

Signal Word

Warning

Hazard Statements

H317,H319,H341,H400

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000489022
0000489022
0000360769
0000360769
0000187253

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Zheng Liu et al.
Oncoimmunology, 9(1), 1758003-1758003 (2020-09-15)
Despite some of the oncogenic driver mutations that have been associated with increased expression of programmed death-ligand 1 (PD-L1), the correlation between PD-L1 expression and ROS1 fusion in NSCLC cells, especially for those with Crizotinib resistance has not been fully
Ekaterina Mikhailovna Stasevich et al.
International journal of molecular sciences, 23(9) (2022-05-15)
Chromosomal rearrangements leading to the relocation of proto-oncogenes into transcription-active regions are found in various types of tumors. In particular, the transfer of proto-oncogenes to the locus of heavy chains of immunoglobulins (IGH) is frequently observed in B-lymphomas. The increased
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)
Meiling Zhang et al.
Frontiers in pharmacology, 12, 759267-759267 (2021-10-12)
Background: Crizotinib is a microtubule-related protein-4-anaplastic lymphoma kinase (EML4-ALK) multi-target tyrosine kinase inhibitor applied in the treatment of ALK-rearranged NSCLC. However, the specific molecular mechanism underlying its therapeutic effect remains unclear. Therefore, the purpose of this research is to explore
Nicole R Infarinato et al.
Cancer discovery, 6(1), 96-107 (2015-11-12)
Neuroblastomas harboring activating point mutations in anaplastic lymphoma kinase (ALK) are differentially sensitive to the ALK inhibitor crizotinib, with certain mutations conferring intrinsic crizotinib resistance. To overcome this clinical obstacle, our goal was to identify inhibitors with improved potency that
View All Related Papers

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