pyrotinib   Click here for help

GtoPdb Ligand ID: 9662

Synonyms: Airuini® | compound 12 [PMID: 28115222] | SHR-1258 | SHR1258
Approved drug
pyrotinib is an approved drug (China (2018))
Compound class: Synthetic organic
Comment: Pyrotinib (SHR1258) is an orally administered, irreversible inhibitor of the tyrosine kinase activities of the EGFR (HER1), HER2 and HER4 [1-2]. It is claimed as example 5 in patent US20120165352 [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 112.4
Molecular weight 582.21
XLogP 4.47
No. Lipinski's rules broken 0
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Canonical SMILES CCOc1cc2ncc(c(c2cc1NC(=O)C=CC1CCCN1C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
Isomeric SMILES CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/[C@H]1CCCN1C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
InChI InChI=1S/C32H31ClN6O3/c1-3-41-30-17-27-25(16-28(30)38-31(40)12-10-24-8-6-14-39(24)2)32(21(18-34)19-36-27)37-22-9-11-29(26(33)15-22)42-20-23-7-4-5-13-35-23/h4-5,7,9-13,15-17,19,24H,3,6,8,14,20H2,1-2H3,(H,36,37)(H,38,40)/b12-10+/t24-/m1/s1
1. Li X, Yang C, Wan H, Zhang G, Feng J, Zhang L, Chen X, Zhong D, Lou L, Tao W et al.. (2017)
Discovery and development of pyrotinib: A novel irreversible EGFR/HER2 dual tyrosine kinase inhibitor with favorable safety profiles for the treatment of breast cancer.
Eur J Pharm Sci, 110: 51-61. [PMID:28115222]
2. Ma F, Li Q, Chen S, Zhu W, Fan Y, Wang J, Luo Y, Xing P, Lan B, Li M et al.. (2017)
Phase I Study and Biomarker Analysis of Pyrotinib, a Novel Irreversible Pan-ErbB Receptor Tyrosine Kinase Inhibitor, in Patients With Human Epidermal Growth Factor Receptor 2-Positive Metastatic Breast Cancer.
J Clin Oncol, 35 (27): 3105-3112. [PMID:28498781]
3. Tang PC, Li X, Wang J, Chen L. (2012)
6-amino quinazoline or 3-cyano quinoline derivatives, preparation methods and pharmaceutical uses thereof.
Patent number: US20120165352. Assignee: Bevollmächtigter Shanghai Hengrui Pharmaceutical Co., Ltd., Jiangsu Hengrui Medicine Co., Ltd.. Priority date: 14/09/2009. Publication date: 28/06/2012.