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].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
Pyrotinib is being evaluated in clinical trials for efficacy in HER2-positive solid tumours, including metastatic breast cancer, gastric cancer, or other solid tumours that have no targeted agent as standard of care. Results from a Phase 1 study (NCT01937689) in patients with metastatic breast cancer are reported by Ma et al. (2017), in which encouraging antitumour activity in these patients was detected [2]. Pyrotinib was approved for use in China in 2018, indicated for breast cancer.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01937689 Study of Pyrotinib in Patients With Human Epidermalgrowth Factor Receptor 2 (HER2) Positive Advanced Breast Cancer Phase 1 Interventional Jiangsu HengRui Medicine Co., Ltd.
NCT02500199 Phase I Study of Pyrotinib in Patients With HER2-positive Solid Tumors Phase 1 Interventional Hengrui Therapeutics, Inc.
Pharmacokinetics Click here for help
Principally metabolised by CYP3A4 (> 75% metabolised in an in vitro liver microsomal stability assay), with a minor contribution by CYP3A5 [1].