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877399-52-5,MFCD12407409
Catalog No.:AA00368K

877399-52-5 | Crizotinib

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
98%
in stock  
$6.00   $4.00
- +
10mg
98%
in stock  
$7.00   $5.00
- +
100mg
98%
in stock  
$18.00   $13.00
- +
250mg
98%
in stock  
$23.00   $16.00
- +
1g
98%
in stock  
$89.00   $62.00
- +
5g
98%
in stock  
$198.00   $139.00
- +
25g
95%
in stock  
$834.00   $584.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00368K
Chemical Name:
Crizotinib
CAS Number:
877399-52-5
Molecular Formula:
C21H22Cl2FN5O
Molecular Weight:
450.3367
MDL Number:
MFCD12407409
SMILES:
Nc1ncc(cc1O[C@@H](c1c(Cl)ccc(c1Cl)F)C)c1cnn(c1)C1CCNCC1
NSC Number:
749005
Properties
Properties
 
BP:
599.177°C at 760 mmHg  
Form:
Solid  
Storage:
Light sensitive;Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
558  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
3.7  

Downstream Synthesis Route
CASUnavailable 
  877399-52-5 

[1]Locationinpatent:experimentalpartCui,J.Jean;Tran-Dubé,Michelle;Shen,Hong;Nambu,Mitchell;Kung,Pei-Pei;Pairish,Mason;Jia,Lei;Meng,Jerry;Funk,Lee;Botrous,Iriny;McTigue,Michele;Grodsky,Neil;Ryan,Kevin;Padrique,Ellen;Alton,Gordon;Timofeevski,Sergei;Yamazaki,Shinji;Li,Qiuhua;Zou,Helen;Christensen,James;Mroczkowski,Barbara;Bender,Steve;Kania,RobertS.;Edwards,MartinP.[JournalofMedicinalChemistry,2011,vol.54,#18,p.6342-6363]

[2]CurrentPatentAssignee:XIHUAUNIVERSITY-CN105294657,2016,ALocationinpatent:Paragraph0050;0057-0059

[3]CurrentPatentAssignee:HENANTECHNICALINSTITUTE-CN106632263,2017,ALocationinpatent:Paragraph0054;0055;0056;0057;0058

[4]CurrentPatentAssignee:ZHENGZHOUTETRANOVPHARMACEUTICAL-CN106496192,2017,ALocationinpatent:Paragraph0049;0051;0057

[5]CurrentPatentAssignee:SHANGHAIFOSUNPHARMACEUTICAL(GROUP)CO.,LTD.-CN111349082,2020,ALocationinpatent:Paragraph0028-0039

[6]Chen,Jianli;Cheng,Pengfei;Su,Weike;Xie,Xiaoxuan;Xu,Feng;Yu,Zhiqun[OrganicProcessResearchandDevelopment,2020,vol.24,#10,p.2252-2259]

[7]CurrentPatentAssignee:JINANTRIOPHARMATECH-CN103664896,2016,BLocationinpatent:Paragraph0116;0117

[8]Locationinpatent:experimentalpartDeKoning,PieterD.;McAndrew,Douglas;Moore,Robert;Moses,IanB.;Boyles,DavidC.;Kissick,Kyle;Stanchina,CoreyL.;Cuthbertson,Timothy;Kamatani,Asayuki;Rahman,Leera;Rodriguez,Rick;Urbina,Armando;SandovalneeAccacia,Alison;Rose,PeterR.[Organicprocessresearchanddevelopment,2011,vol.15,#5,p.1018-1026]

[9]CurrentPatentAssignee:SHANGHAIACANAPHARMTECH-CN106317024,2017,ALocationinpatent:Paragraph0069;0070;0071;0072;0073

[10]CurrentPatentAssignee:PFIZERINC-WO2006/21881,2006,A2Locationinpatent:Page/Pagecolumn71;72

[11]CurrentPatentAssignee:PFIZERINC-US2008/293769,2008,A1Locationinpatent:Page/Pagecolumn7

[12]CurrentPatentAssignee:PFIZERINC-WO2013/17989,2013,A1Locationinpatent:Page/Pagecolumn68;69

[13]CurrentPatentAssignee:FRESENIUSSE&CO.KGAA-WO2014/20467,2014,A2Locationinpatent:Page/Pagecolumn22

[14]CurrentPatentAssignee:IPGESFURMAN-EP2764866,2014,A1Locationinpatent:Paragraph0056

[15]CurrentPatentAssignee:WUYANGWEISENBIOMEDICINE;JIANGSUSWELLXINBIOPHARMACEUTICALENGINEERINGRE;ZHANGJIAGANGWEISHENGBIOLOGICALMEDICAL-CN107417603,2017,ALocationinpatent:Paragraph0021

[16]CurrentPatentAssignee:PFIZERINC-US2016/206608,2016,A1Locationinpatent:Paragraph0267;0269

[17]CurrentPatentAssignee:SHANGHAIFOSUNPHARMACEUTICAL(GROUP)CO.,LTD.-CN115611861,2023,ALocationinpatent:Paragraph0048-0050

CASUnavailable 
 
CASUnavailable 
  877399-52-5 

[1]CurrentPatentAssignee:PFIZERINC-US2008/300273,2008,A1

[1]CurrentPatentAssignee:TEVAPHARMACEUTICALINDUSTRIESLTD.-WO2013/181251,2013,A1Locationinpatent:Page/Pagecolumn24;25

[1]CurrentPatentAssignee:TEVAPHARMACEUTICALINDUSTRIESLTD.-WO2013/181251,2013,A1Locationinpatent:Page/Pagecolumn29

[1]CurrentPatentAssignee:TEVAPHARMACEUTICALINDUSTRIESLTD.-WO2013/181251,2013,A1Locationinpatent:Page/Pagecolumn25

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Title: Activating ALK mutations found in neuroblastoma are inhibited by Crizotinib and NVP-TAE684.

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Journal: Drugs 20111203

Title: ALK mutations conferring differential resistance to structurally diverse ALK inhibitors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111201

Title: New strategies for treatment of ALK-rearranged non-small cell lung cancers.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111201

Title: Crizotinib-resistant mutants of EML4-ALK identified through an accelerated mutagenesis screen.

Journal: Chemical biology & drug design 20111201

Title: Asymptomatic profound sinus bradycardia (heart rate ≤45) in non-small cell lung cancer patients treated with crizotinib.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20111201

Title: Crizotinib.

Journal: Nature reviews. Drug discovery 20111201

Title: Incorporation of crizotinib into the NCCN guidelines.

Journal: Journal of the National Comprehensive Cancer Network : JNCCN 20111201

Title: Crizotinib and testing for ALK.

Journal: Journal of the National Comprehensive Cancer Network : JNCCN 20111201

Title: Targeted treatment tested as potential cancer cure.

Journal: Nature 20111116

Title: Differential inhibitor sensitivity of anaplastic lymphoma kinase variants found in neuroblastoma.

Journal: Science translational medicine 20111109

Title: Larger companies dominate cancer companion diagnostic approvals.

Journal: Nature biotechnology 20111108

Title: Anaplastic lymphoma kinase as a new target for the treatment of non-small-cell lung cancer.

Journal: Expert review of anticancer therapy 20111101

Title: Proof of principle for crizotinib in anaplastic lymphoma kinase-positive malignancies was achieved in ALK-positive nonclinical models.

Journal: Molecular cancer therapeutics 20111101

Title: Treatment for ALK-mutated non-small-cell lung cancer: a new miracle in the research race.

Journal: Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico 20111101

Title: The potential for crizotinib in non-small cell lung cancer: a perspective review.

Journal: Therapeutic advances in medical oncology 20111101

Title: Comprehensive analysis of kinase inhibitor selectivity.

Journal: Nature biotechnology 20111030

Title: MET tyrosine kinase inhibitor crizotinib (PF-02341066) shows differential antitumor effects in non-small cell lung cancer according to MET alterations.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20111001

Title: Effect of crizotinib on overall survival in patients with advanced non-small-cell lung cancer harbouring ALK gene rearrangement: a retrospective analysis.

Journal: The Lancet. Oncology 20111001

Title: Hope without hype: EML4-ALK inhibition for treatment of lung cancer.

Journal: The Lancet. Oncology 20111001

Title: Emerging importance of ALK in neuroblastoma.

Journal: Seminars in cancer biology 20111001

Title: Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK).

Journal: Journal of medicinal chemistry 20110922

Title: 9-substituted 6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazoles as highly selective and potent anaplastic lymphoma kinase inhibitors.

Journal: Journal of medicinal chemistry 20110922

Title: A novel ALK secondary mutation and EGFR signaling cause resistance to ALK kinase inhibitors.

Journal: Cancer research 20110915

Title: Anaplastic lymphoma kinase in human cancer.

Journal: Journal of molecular endocrinology 20110801

Title: Detection of ALK gene rearrangement in non-small cell lung cancer: a comparison of fluorescence in situ hybridization and chromogenic in situ hybridization with correlation of ALK protein expression.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110801

Title: Synthesis of an aryloxy oxo pyrimidinone library that displays ALK-selective inhibition.

Journal: Bioorganic & medicinal chemistry letters 20110801

Title: Differential (18)F-FDG and 3'-deoxy-3'-(18)F-fluorothymidine PET responses to pharmacologic inhibition of the c-MET receptor in preclinical tumor models.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20110801

Title: Favorable response to crizotinib in three patients with echinoderm microtubule-associated protein-like 4-anaplastic lymphoma kinase fusion-type oncogene-positive non-small cell lung cancer.

Journal: Cancer science 20110801

Title: Receptor kinase inhibitors target NSCLC: two antibodies and a small-molecule MET inhibitor.

Journal: BioDrugs : clinical immunotherapeutics, biopharmaceuticals and gene therapy 20110801

Title: Crizotinib: an anaplastic lymphoma kinase inhibitor.

Journal: Future oncology (London, England) 20110801

Title: Phase 1 clinical trials for sarcomas: the cutting edge.

Journal: Current opinion in oncology 20110701

Title: [Molecular targeted drugs against ALK fusions].

Journal: Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20110701

Title: The orally bioavailable met inhibitor PF-2341066 inhibits osteosarcoma growth and osteolysis/matrix production in a xenograft model.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20110601

Title: [What choice of first-line treatment?].

Journal: Revue de pneumologie clinique 20110601

Title: [What is the best sequence of treatment for patients with EGFR mutations?].

Journal: Revue de pneumologie clinique 20110601

Title: [Biomarkers and targeted therapies in non-small cell lung cancer: present and future treatments].

Journal: Revue de pneumologie clinique 20110601

Title: ALK-targeted therapy for lung cancer: ready for prime time.

Journal: Oncology (Williston Park, N.Y.) 20110601

Title: CSF concentration of the anaplastic lymphoma kinase inhibitor crizotinib.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20110520

Title: Pulmonary inflammatory myofibroblastic tumor expressing a novel fusion, PPFIBP1-ALK: reappraisal of anti-ALK immunohistochemistry as a tool for novel ALK fusion identification.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110515

Title: Virtual screening and further development of novel ALK inhibitors.

Journal: Bioorganic & medicinal chemistry 20110515

Title: Therapeutic strategies to overcome crizotinib resistance in non-small cell lung cancers harboring the fusion oncogene EML4-ALK.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20110503

Title: 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.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110501

Title: Genotype-driven therapies for non-small cell lung cancer: focus on EGFR, KRAS and ALK gene abnormalities.

Journal: Therapeutic advances in medical oncology 20110501

Title: Targeting anaplastic lymphoma kinase in lung cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110415

Title: Synthesis and c-Met kinase inhibition of 3,5-disubstituted and 3,5,7-trisubstituted quinolines: identification of 3-(4-acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a novel anticancer agent.

Journal: Journal of medicinal chemistry 20110414

Title: Anaplastic lymphoma kinase gene rearrangements in non-small cell lung cancer are associated with prolonged progression-free survival on pemetrexed.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110401

Title: Potential therapeutic strategies to overcome acquired resistance to BRAF or MEK inhibitors in BRAF mutant cancers.

Journal: Oncotarget 20110401

Title: Early accelerated approval for highly targeted cancer drugs.

Journal: The New England journal of medicine 20110324

Title: NSCLC drug targets acquire new visibility.

Journal: Journal of the National Cancer Institute 20110302

Title: Prediction of oral pharmacokinetics of cMet kinase inhibitors in humans: physiologically based pharmacokinetic model versus traditional one-compartment model.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110301

Title: Crizotinib for EML4-ALK positive lung adenocarcinoma: a hope for the advanced disease? Evaluation of Kwak EL, Bang YJ, Camidge DR, et al. Anaplastic lymphoma kinase inhibition in non-small-cell lung cancer. N Engl J Med 2010;363(18):1693-703.

Journal: Expert opinion on therapeutic targets 20110301

Title: Personalizing therapy with targeted agents in non-small cell lung cancer.

Journal: Oncotarget 20110301

Title: New targets in advanced NSCLC: EML4-ALK.

Journal: Clinical advances in hematology & oncology : H&O 20110301

Title: Crizotinib in anaplastic large-cell lymphoma.

Journal: The New England journal of medicine 20110224

Title: More on crizotinib.

Journal: The New England journal of medicine 20110224

Title: More on crizotinib.

Journal: The New England journal of medicine 20110224

Title: More on crizotinib.

Journal: The New England journal of medicine 20110224

Title: Distinct interactions between c-Src and c-Met in mediating resistance to c-Src inhibition in head and neck cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110201

Title: Multiple mutations and bypass mechanisms can contribute to development of acquired resistance to MET inhibitors.

Journal: Cancer research 20110201

Title: Comparison of 2 cell-based phosphoprotein assays to support screening and development of an ALK inhibitor.

Journal: Journal of biomolecular screening 20110201

Title: Kinetic control of protonation in electrospray ionization.

Journal: Journal of the American Society for Mass Spectrometry 20110201

Title: Summary of presentations from the 46th Annual Meeting of the American Society of Clinical Oncology: focus on non-small cell lung cancer (2010).

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110101

Title: MET inhibitors: translating from bench to bedside.

Journal: The Lancet. Oncology 20110101

Title: Gastrointestinal Mesenchymal Neoplasms other than Gastrointestinal Stromal Tumors: Focusing on Their Molecular Aspects.

Journal: Pathology research international 20110101

Title: Targeted therapies and other agents as first-line maintenance and beyond: particular benefit in pulmonary adenocarcinoma patients.

Journal: Current medicinal chemistry 20110101

Title: Wnt signaling and colon carcinogenesis: beyond APC.

Journal: Journal of carcinogenesis 20110101

Title: Novel targeted therapeutics: inhibitors of MDM2, ALK and PARP.

Journal: Journal of hematology & oncology 20110101

Title: Target therapies in lung cancer.

Journal: Journal of biomedicine & biotechnology 20110101

Title: Inhibitor-sensitive FGFR1 amplification in human non-small cell lung cancer.

Journal: PloS one 20110101

Title: Advances in fine needle aspiration cytology for the diagnosis of pulmonary carcinoma.

Journal: Pathology research international 20110101

Title: From the bench to bedside: biological and methodology considerations for the future of companion diagnostics in nonsmall cell lung cancer.

Journal: Pathology research international 20110101

Title: Transglutaminase 2 as an independent prognostic marker for survival of patients with non-adenocarcinoma subtype of non-small cell lung cancer.

Journal: Molecular cancer 20110101

Title: Resistance to cancer treatment: the role of somatic genetic events and the challenges for targeted therapies.

Journal: Frontiers in pharmacology 20110101

Title: ALK and NSCLC: Targeted therapy with ALK inhibitors.

Journal: F1000 medicine reports 20110101

Title: Signatures of drug sensitivity in nonsmall cell lung cancer.

Journal: International journal of proteomics 20110101

Title: Spectrum of oncogenic driver mutations in lung adenocarcinomas from East Asian never smokers.

Journal: PloS one 20110101

Title: Crizotinib: a novel and first-in-class multitargeted tyrosine kinase inhibitor for the treatment of anaplastic lymphoma kinase rearranged non-small cell lung cancer and beyond.

Journal: Drug design, development and therapy 20110101

Title: New drug therapies, dedicated specialists and desperately-ill patients-but who will fly the flag for service developments in lung cancer as NHS budgets come under pressure?

Journal: Ecancermedicalscience 20110101

Title: An update on the management of peripheral T-cell lymphoma and emerging treatment options.

Journal: Journal of blood medicine 20110101

Title: Personalized therapy for non-small cell lung cancer: which drug for which patient?

Journal: Seminars in thoracic and cardiovascular surgery 20110101

Title: Anaplastic Lymphoma Kinase: role in specific tumours, and development of small molecule inhibitors for cancer therapy.

Journal: Cancer letters 20101228

Title: The neuroblastoma-associated F1174L ALK mutation causes resistance to an ALK kinase inhibitor in ALK-translocated cancers.

Journal: Cancer research 20101215

Title: ALK inhibition for non-small cell lung cancer: from discovery to therapy in record time.

Journal: Cancer cell 20101214

Title: New drugs in advanced non-small-cell lung cancer: searching for the correct clinical development.

Journal: Expert opinion on investigational drugs 20101201

Title: Parameters for individualizing systemic therapy in non-small cell lung cancer.

Journal: Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20101201

Title: Rapid and dramatic radiographic and clinical response to an ALK inhibitor (crizotinib, PF02341066) in an ALK translocation-positive patient with non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20101201

Title: Trial watch: success for crizotinib in ALK-driven cancer.

Journal: Nature reviews. Drug discovery 20101201

Title: Crizotinib, a small-molecule dual inhibitor of the c-Met and ALK receptor tyrosine kinases.

Journal: Current opinion in investigational drugs (London, England : 2000) 20101201

Title: [Following communications made at American Society of Clinical Oncology 2010, what will change our practice? The point of view of the editorial board of Bulletin du Cancer].

Journal: Bulletin du cancer 20101201

Title: Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.

Journal: Chemistry & biology 20101124

Title: Anaplastic lymphoma kinase inhibition in non-small-cell lung cancer.

Journal: The New England journal of medicine 20101028

Title: Crizotinib in ALK-rearranged inflammatory myofibroblastic tumor.

Journal: The New England journal of medicine 20101028

Title: EML4-ALK mutations in lung cancer that confer resistance to ALK inhibitors.

Journal: The New England journal of medicine 20101028

Title: Crizotinib--latest champion in the cancer wars?

Journal: The New England journal of medicine 20101028

Title: Exciting new targets in lung cancer therapy: ALK, IGF-1R, HDAC, and Hh.

Journal: Current treatment options in oncology 20100601

Title: Gender specific drug metabolism of PF-02341066 in rats--role of sulfoconjugation.

Journal: Current drug metabolism 20100501

Title: Discovery of 6-benzyloxyquinolines as c-Met selective kinase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20100215

Title: Acquired resistance of non-small cell lung cancer cells to MET kinase inhibition is mediated by a switch to epidermal growth factor receptor dependency.

Journal: Cancer research 20100215

Title: An orally available small-molecule inhibitor of c-Met, PF-2341066, reduces tumor burden and metastasis in a preclinical model of ovarian cancer metastasis.

Journal: Neoplasia (New York, N.Y.) 20100101

Title: Efficacy of c-Met inhibitor for advanced prostate cancer.

Journal: BMC cancer 20100101

Title: Deciding priorities in Pharma.

Journal: Breast cancer research : BCR 20100101

Title: HGF and c-Met participate in paracrine tumorigenic pathways in head and neck squamous cell cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090601

Title: An orally available small-molecule inhibitor of c-Met, PF-2341066, exhibits cytoreductive antitumor efficacy through antiproliferative and antiangiogenic mechanisms.

Journal: Cancer research 20070501

Title: Zou HY, 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(9), 4408-4417.

Title: Christensen JG, et al. Cytoreductive antitumor activity of PF-2341066, a novel inhibitor of anaplastic lymphoma kinase and c-Met, in experimental models of anaplastic large-cell lymphoma. Mol Cancer Ther. 2007, 6(12 Pt 1), 3314-3322.

Title: Cui JJ, et al. Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). J Med Chem. 2011 Sep 22;54(18):6342-63.

Title: Cullinane C, et al. Differential (18)F-FDG and 3'-deoxy-3'-(18)F-fluorothymidine PET responses to pharmacologic inhibition of the c-MET receptor in preclinical tumor models. J Nucl Med. 2011 Aug;52(8):1261-7

Title: Shen A, et al. c-Myc alterations confer therapeutic response and acquired resistance to c-Met inhibitors in MET-addicted cancers. Cancer Res. 2015 Nov 1;75(21):4548-59.

Title: Umapathy G, et al. The kinase ALK stimulates the kinase ERK5 to promote the expression of the oncogene MYCN in neuroblastoma. Sci Signal. 2014 Oct 28;7(349):ra102.

Title: Tucker ER, et al. Immunoassays for the quantification of ALK and phosphorylated ALK support the evaluation of on-target ALK inhibitors in neuroblastoma. Mol Oncol. 2017 Aug;11(8):996-1006.

Title: Liu H, et al. Identifying and Targeting Sporadic Oncogenic GeneticLiu H, et al. Identifying and Targeting Sporadic Oncogenic Genetic Aberrations in Mouse Models of Triple Negative Breast Cancer. Cancer Discov. 2018 Mar;8(3):354-369.

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Tags:877399-52-5 Molecular Formula|877399-52-5 MDL|877399-52-5 SMILES|877399-52-5 Crizotinib