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877399-52-5 分子结构
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3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine

ChemBase编号:6303
分子式:C21H22Cl2FN5O
平均质量:450.3366832
单一同位素质量:449.11854393
SMILES和InChIs

SMILES:
Clc1ccc(F)c(c1[C@@H](C)Oc1cc(cnc1N)c1cnn(c1)C1CCNCC1)Cl
Canonical SMILES:
Nc1ncc(cc1O[C@@H](c1c(Cl)ccc(c1Cl)F)C)c1cnn(c1)C1CCNCC1
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

引用这个纪录

CBID:6303 http://www.chembase.cn/molecule-6303.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine
IUPAC传统名
crizotinib
别名
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-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine
PF-02341066
Crizotinib
PF-2341066
(R)-3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine
PF 2341066
PF02341066
Xalkori
Crizotinib
CAS号
877399-52-5
MDL号
MFCD12407409
PubChem SID
160969694
PubChem CID
11626560

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) -0.118933685  LogD (pH = 7.4) 0.9544419 
Log P 3.5741167  摩尔折射率 128.4316 cm3
极化性 45.653618 Å3 极化表面积 77.99 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 3.82  LOG S -4.87 
溶解度 6.11e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
外观
white to tan powder expand 查看数据来源
保存条件
-20°C expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
TSCA收录
false expand 查看数据来源
保存温度
room temp expand 查看数据来源
作用靶点
ALK expand 查看数据来源
c-Met expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
Empirical Formula (Hill Notation)
C21H22Cl2FN5O expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank -  DB08700 external link
Drug information: experimental
Selleck Chemicals -  S1068 external link
Research Area
Description Cancer
Protocol
Kinase Assay [1]
Biochemical kinase assays c-Met catalytic activity is quantitated using a continuous-coupled spectrophotometric assay in which the time-dependent production of ADP by c-Met is determined by analysis of the rate of consumption of NADH. NADH consumption is measured by a decrease in absorbance at 340 nm by spectrophotometry at designated time points. To determine Ki values, PF-2341066 is introduced into test wells at various concentrations in the presence of assay reagents and incubated for 10 minutes at 37 °C. The assay is initiated by the addition of the c-Met enzyme.
Cell Assay [1]
Cell Lines GTL-16 gastric carcinoma cells and T47D breast carcinoma cells
Concentrations 0-256 nM
Incubation Time 1 hour
Methods Cells including GTL-16 gastric carcinoma cells and T47D breast carcinoma cells are seeded in 96-well plates in media supplemented with 10% fetal bovine serum (FBS) and transferred to serum-free media [with 0.04% bovine serum albumin (BSA)] after 24 hours. In experiments investigating ligand-dependent RTK phosphorylation, corresponding growth factors are added for up to 20 minutes. After incubation of cells with PF-2341066 for 1 hour and/or appropriate ligands for the designated times, cells are washed once with HBSS supplemented with 1 mM Na3VO4, and protein lysates are generated from cells. Subsequently, phosphorylation of selected protein kinases is assessed by a sandwich ELISA method using specific capture antibodies used to coat 96-well plates and a detection antibody specific for phosphorylated tyrosine residues. Antibody-coated plates are (a) incubated in the presence of protein lysates at 4 °C overnight; (b) washed seven times in 1% Tween 20 in PBS; (c) incubated in a horseradish peroxidase–conjugated anti–total-phosphotyrosine (PY-20) antibody (1:500) for 30 min; (d) washed seven times again; (e) incubated in 3,3,5,5-tetramethyl benzidine peroxidase substrate to initiate a colorimetric reaction that is stopped by adding 0.09 N H2SO4; and (f) measured for absorbance in 450 nm using a spectrophotometer.
Animal Study [1]
Animal Models Female or male nu/nu mice bearing NCI-H441,or DLD-1, or MDA-MB-231
Formulation
Doses 12.5 mg/kg/day, 25 mg/kg/day, and 50 mg/kg/day
Administration Administered via p.o.
References
[1] Zou HY, et al. Cancer Res. 2007, 67(9), 4408-4417.
[2] Christensen JG, et al. Mol Cancer Ther. 2007, 6(12 Pt 1), 3314-3322.
[3] Sampson ER, et al. J Bone Miner Res. 2011, 26(6), 1283-1294.
[4] Cullinane C, et al. J Nucl Med. 2011, 52(8), 1261-1267.
[5] Gong HC, et al. Int J Proteomics. 2011, 2011, 215496.
Sigma Aldrich -  PZ0191 external link
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
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). It is a highly specific inhibitor of c-Met and ALK among > 120 different RTKs surveyed. Crizotinib was recently approved for treatment of a subtype of nonsmall-cell lung cancer (NSCLC) with ALK fusion mutations.

专利

专利

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