Pelitinib, also known as EKB569 and WAY-172569, is a 3-cyanoquinoline pan-ErbB tyrosine kinase inhibitor with potential antineoplastic activity. EKB-569 irreversibly binds covalently to epidermal growth factor receptors (EGFR) ErbB-1, -2 and -4, thereby inhibiting receptor phosphorylation and signal transduction and resulting in apoptosis and suppression of proliferation in tumor cells that overexpress these receptors. MedKoo Cat#: 202190 Name: Pelitinib CAS#: 257933-82-7 Chemical Formula: C24H23ClFN5O2 Exact Mass: 467.15243 Molecular Weight: 467.92 Elemental Analysis: C, 61.60; H, 4.95; Cl, 7.58; F, 4.06; N, 14.97; O, 6.84 Synonym: EKB569; EKB-569; EKB 569; WAY-172569; WAY 172569; WAY172569; Pelitinib IUPAC/Chemical Name: (E)-N-(4-((3-chloro-4-fluorophenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide InChi Key: WVUNYSQLFKLYNI-AATRIKPKSA-N InChi Code: InChI=1S/C24H23ClFN5O2/c1-4-33-22-12-20-17(11-21(22)30-23(32)6-5-9-31(2)3)24(15(13-27)14-28-20)29-16-7-8-19(26)18(25)10-16/h5-8,10-12,14H,4,9H2,1-3H3,(H,28,29)(H,30,32)/b6-5+ SMILES Code: O=C(NC1=C(OCC)C=C2N=CC(C#N)=C(NC3=CC=C(F)C(Cl)=C3)C2=C1)/C=C/CN(C)C Technical Data Appearance: White to off white powder Purity: >98% (or refer to the Certificate of Analysis) Certificate of Analysis: View CoA: current batch, Lot#CRB61102 QC Data: View QC data: current batch, Lot#CRB61102 Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS) Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Solubility: Soluble in DMSO, not soluble in water. Shelf Life: >5 years if stored properly Drug Formulation: This drug may be formulated in DMSO Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months). Harmonized System Code: 293490 Additional Information    References 1: Maher HM, Alzoman NZ, Shehata SM. An eco-friendly direct spectrofluorimetric method for the determination of irreversible tyrosine kinase inhibitors, neratinib and pelitinib: application to stability studies. Luminescence. 2016 Jun 1. doi: 10.1002/bio.3160. PubMed PMID: 27246364. 2: To KK, Poon DC, Wei Y, Wang F, Lin G, Fu L. Pelitinib (EKB-569) targets the up-regulation of ABCB1 and ABCG2 induced by hyperthermia to eradicate lung cancer. Br J Pharmacol. 2015 Aug;172(16):4089-106. doi: 10.1111/bph.13189. PubMed PMID: 25988710; PubMed Central PMCID: PMC4543615. 3: Wiewrodt R, Serke M, Grohé C, Brückl W. [Employing tyrosine kinase inhibitors in the first line treatment of EGFR-positive metastatic NSCLC - state of the art and recent developments]. Pneumologie. 2013 Sep;67(9):494-501. doi: 10.1055/s-0033-1344337. Review. German. PubMed PMID: 24006195. 4: Luethi D, Durmus S, Schinkel AH, Schellens JH, Beijnen JH, Sparidans RW. Liquid chromatography-tandem mass spectrometry assay for the EGFR inhibitor pelitinib in plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Sep 1;934:22-5. doi: 10.1016/j.jchromb.2013.06.030. PubMed PMID: 23892825. 5: Aravindan N, Aravindan S, Herman TS, Natarajan M. EGFR tyrosine kinase inhibitor pelitinib regulates radiation-induced p65-dependent telomerase activation in squamous cell carcinoma. Radiat Res. 2013 Mar;179(3):304-12. doi: 10.1667/RR3028.1. PubMed PMID: 23379415. 6: Majem M, Pallarès C. An update on molecularly targeted therapies in second- and third-line treatment in non-small cell lung cancer: focus on EGFR inhibitors and anti-angiogenic agents. Clin Transl Oncol. 2013 May;15(5):343-57. doi: 10.1007/s12094-012-0964-2. Review. PubMed PMID: 23359171. 7: Crabtree JE, Jeremy AH, Duval C, Dixon MF, Danjo K, Carr IM, Pritchard DM, Robinson PA. Effects of EGFR Inhibitor on Helicobacter pylori Induced Gastric Epithelial Pathology in Vivo. Pathogens. 2013 Oct 14;2(4):571-90. doi: 10.3390/pathogens2040571. PubMed PMID: 25437333; PubMed Central PMCID: PMC4235704. 8: Hegedüs C, Truta-Feles K, Antalffy G, Várady G, Német K, Ozvegy-Laczka C, Kéri G, Orfi L, Szakács G, Settleman J, Váradi A, Sarkadi B. Interaction of the EGFR inhibitors gefitinib, vandetanib, pelitinib and neratinib with the ABCG2 multidrug transporter: implications for the emergence and reversal of cancer drug resistance. Biochem Pharmacol. 2012 Aug 1;84(3):260-7. doi: 10.1016/j.bcp.2012.04.010. PubMed PMID: 22548830. 9: Aravindan N, Thomas CR Jr, Aravindan S, Mohan AS, Veeraraghavan J, Natarajan M. Irreversible EGFR inhibitor EKB-569 targets low-LET γ-radiation-triggered rel orchestration and potentiates cell death in squamous cell carcinoma. PLoS One. 2011;6(12):e29705. doi: 10.1371/journal.pone.0029705. PubMed PMID: 22242139; PubMed Central PMCID: PMC3248439. 10: Kim H, Lim HY. Novel EGFR-TK inhibitor EKB-569 inhibits hepatocellular carcinoma cell proliferation by AKT and MAPK pathways. J Korean Med Sci. 2011 Dec;26(12):1563-8. doi: 10.3346/jkms.2011.26.12.1563. PubMed PMID: 22147992; PubMed Central PMCID: PMC3230015. 11: Bryce AH, Rao R, Sarkaria J, Reid JM, Qi Y, Qin R, James CD, Jenkins RB, Boni J, Erlichman C, Haluska P. Phase I study of temsirolimus in combination with EKB-569 in patients with advanced solid tumors. Invest New Drugs. 2012 Oct;30(5):1934-41. doi: 10.1007/s10637-011-9742-1. PubMed PMID: 21881915; PubMed Central PMCID: PMC3816525. 12: Sánchez-Martín M, Pandiella A. Differential action of small molecule HER kinase inhibitors on receptor heterodimerization: therapeutic implications. Int J Cancer. 2012 Jul 1;131(1):244-52. doi: 10.1002/ijc.26358. PubMed PMID: 21826647. 13: Brünner-Kubath C, Shabbir W, Saferding V, Wagner R, Singer CF, Valent P, Berger W, Marian B, Zielinski CC, Grusch M, Grunt TW. The PI3 kinase/mTOR blocker NVP-BEZ235 overrides resistance against irreversible ErbB inhibitors in breast cancer cells. Breast Cancer Res Treat. 2011 Sep;129(2):387-400. doi: 10.1007/s10549-010-1232-1. PubMed PMID: 21046231. 14: Liu B, You QD, Li ZY. [Synthesis and biological evaluation of 3-quinolinecarbonitrile-7-amide derivatives]. Yao Xue Xue Bao. 2009 Aug;44(8):879-84. Chinese. PubMed PMID: 20055156. 15: Ocaña A, Amir E. Irreversible pan-ErbB tyrosine kinase inhibitors and breast cancer: current status and future directions. Cancer Treat Rev. 2009 Dec;35(8):685-91. doi: 10.1016/j.ctrv.2009.08.001. Review. PubMed PMID: 19733440. 16: Akbulut T, Regner KR, Roman RJ, Avner ED, Falck JR, Park F. 20-HETE activates the Raf/MEK/ERK pathway in renal epithelial cells through an EGFR- and c-Src-dependent mechanism. Am J Physiol Renal Physiol. 2009 Sep;297(3):F662-70. doi: 10.1152/ajprenal.00146.2009. PubMed PMID: 19570883; PubMed Central PMCID: PMC2739708. 17: Grunt TW, Wagner R, Grusch M, Berger W, Singer CF, Marian B, Zielinski CC, Lupu R. Interaction between fatty acid synthase- and ErbB-systems in ovarian cancer cells. Biochem Biophys Res Commun. 2009 Jul 31;385(3):454-9. doi: 10.1016/j.bbrc.2009.05.085. PubMed PMID: 19467222. 18: Barlesi F, Breen D. [Targeting HER pathway in head and neck and thoracic cancers]. Bull Cancer. 2009;96 Suppl 1:S35-43. doi: 10.1684/bdc.2008.0774. Review. French. PubMed PMID: 19433372. 19: Laheru D, Croghan G, Bukowski R, Rudek M, Messersmith W, Erlichman C, Pelley R, Jimeno A, Donehower R, Boni J, Abbas R, Martins P, Zacharchuk C, Hidalgo M. A phase I study of EKB-569 in combination with capecitabine in patients with advanced colorectal cancer. Clin Cancer Res. 2008 Sep 1;14(17):5602-9. doi: 10.1158/1078-0432.CCR-08-0433. PubMed PMID: 18765554; PubMed Central PMCID: PMC3086427. 20: Crespo A, Zhang X, Fernández A. Redesigning kinase inhibitors to enhance specificity. J Med Chem. 2008 Aug 28;51(16):4890-8. doi: 10.1021/jm800453a. PubMed PMID: 18680272.