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Merck
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PZ0240

Sigma-Aldrich

(S)-Crizotinib

≥98% (HPLC)

Synonyme(s) :

3-[(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1H-pyrazol-4-yl]-2-pyridinamine

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About This Item

Formule empirique (notation de Hill):
C21H22Cl2FN5O
Numéro CAS:
1374356-45-2
Poids moléculaire :
450.34
Numéro MDL:
MFCD22126092
Code UNSPSC :
12352200
ID de substance PubChem :
329823787
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear (warmed)

Température de stockage

room temp

Chaîne SMILES 

ClC1=C([C@H](C)OC2=C(N)N=CC(C3=CN(C4CCNCC4)N=C3)=C2)C(Cl)=C(F)C=C1

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-/m0/s1

Clé InChI

KTEIFNKAUNYNJU-LBPRGKRZSA-N

Actions biochimiques/physiologiques

(S)-Crizotinib has a distinctly different profile from its (R)-enantiomer, the clinically approved anticancer agent Xalkori. Instead of targeting ALK, MET and ROS1, (S)-Crizotinib is a highly selective inhibitor of human 7,8-Dihydro-8-oxoguaninetriphosphatase MTH1 (NUDT1) with an IC50 value of 330 nM, 16-fold higher affinity towards MTH1 compared to the clinically used (R)-isomer. MTH1 hydrolyzes oxidized purine nucleoside triphosphates that might otherwise be incorporated into DNA/RNA and contribute to DNA damage. MTH1 removal of oxidized nucleotides that result from increased levels of reactive oxygen species (ROS) in fast-proliferating cancer cells helps protect cancer cells from proliferative stress and prevent cancer cell death. It is considered a new target for cancer therapy. In mouse xenograft studies using SW480 cells, (S)-crizotinib but not the (R)-enantiomer, was able to impair overall tumour progression as well as specifically reduce tumour volume by more than 50%.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Melike Çağlayan et al.
Nature communications, 8, 14045-14045 (2017-01-10)
Oxidative stress in cells can lead to accumulation of reactive oxygen species and oxidation of DNA precursors. Oxidized purine nucleotides can be inserted into DNA during replication and repair. The main pathway for correcting oxidized bases in DNA is base
Xuanxuan Dai et al.
Journal of experimental & clinical cancer research : CR, 36(1), 120-120 (2017-09-09)
Non-small cell lung cancer (NSCLC) accounts for approximately 80-85% of all lung cancers and is usually diagnosed at an advanced stage with poor prognosis. Targeted therapy has produced unprecedented outcomes in patients with NSCLC as a number of oncogenic drivers
Peng Liu et al.
Nature communications, 10(1), 1486-1486 (2019-04-04)
Immunogenic cell death (ICD) converts dying cancer cells into a therapeutic vaccine and stimulates antitumor immune responses. Here we unravel the results of an unbiased screen identifying high-dose (10 µM) crizotinib as an ICD-inducing tyrosine kinase inhibitor that has exceptional antineoplastic
Stefan Nagel et al.
Oncotarget, 11(34), 3208-3226 (2020-09-15)
NKL homeobox genes encode developmental transcription factors and display an NKL-code according to their physiological expression pattern in hematopoiesis. Here, we analyzed public transcriptome data from primary innate lymphoid cells (ILCs) for NKL homeobox gene activities and found that ILC3
Liwei Dong et al.
OncoTargets and therapy, 8, 3649-3664 (2015-12-18)
Inhibition of the nucleotide pool sanitizing enzyme MTH1 causes extensive oxidative DNA damages and apoptosis in cancer cells and hence may be used as an anticancer strategy. As natural products have been a rich source of medicinal chemicals, in the

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