barasertib   Click here for help

GtoPdb Ligand ID: 7332

Synonyms: AZD1152
Compound class: Synthetic organic
Comment: Barasertib is a pro-drug. The phosphate group is rapidly converted to a hydroxyl group in vivo generating the active form which is a selective inhibitor of aurora kinase B.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 16
Topological polar surface area 184.63
Molecular weight 587.21
XLogP 2.11
No. Lipinski's rules broken 2
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Canonical SMILES CCN(CCOP(=O)(O)O)CCCOc1ccc2c(c1)ncnc2Nc1n[nH]c(c1)CC(=O)Nc1cccc(c1)F
Isomeric SMILES CCN(CCOP(=O)(O)O)CCCOc1ccc2c(c1)ncnc2Nc1n[nH]c(c1)CC(=O)Nc1cccc(c1)F
InChI InChI=1S/C26H31FN7O6P/c1-2-34(10-12-40-41(36,37)38)9-4-11-39-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(35)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17H,2,4,9-12,15H2,1H3,(H,30,35)(H2,36,37,38)(H2,28,29,31,32,33)
1. Andrews PD. (2005)
Aurora kinases: shining lights on the therapeutic horizon?.
Oncogene, 24 (32): 5005-15. [PMID:16049526]
2. Carvajal RD, Tse A, Schwartz GK. (2006)
Aurora kinases: new targets for cancer therapy.
Clin Cancer Res, 12 (23): 6869-75. [PMID:17145803]
3. Keen N, Taylor S. (2004)
Aurora-kinase inhibitors as anticancer agents.
Nat Rev Cancer, 4 (12): 927-36. [PMID:15573114]
4. Keen N, Taylor S. (2009)
Mitotic drivers--inhibitors of the Aurora B Kinase.
Cancer Metastasis Rev, 28 (1-2): 185-95. [PMID:19189202]
5. Schwartz GK, Carvajal RD, Midgley R, Rodig SJ, Stockman PK, Ataman O, Wilson D, Das S, Shapiro GI. (2013)
Phase I study of barasertib (AZD1152), a selective inhibitor of Aurora B kinase, in patients with advanced solid tumors.
Invest New Drugs, 31 (2): 370-80. [PMID:22661287]
6. Yang J, Ikezoe T, Nishioka C, Tasaka T, Taniguchi A, Kuwayama Y, Komatsu N, Bandobashi K, Togitani K, Koeffler HP et al.. (2007)
AZD1152, a novel and selective aurora B kinase inhibitor, induces growth arrest, apoptosis, and sensitization for tubulin depolymerizing agent or topoisomerase II inhibitor in human acute leukemia cells in vitro and in vivo.
Blood, 110 (6): 2034-40. [PMID:17495131]