cenisertib   Click here for help

GtoPdb Ligand ID: 9927

Synonyms: AS-703569 | AS703569 [1] | compound 2 [PMID: 22695126] | compound 60a [WO2005118544A2] | enantiomer E1 [WO2005118544A2] | R-763 | R763
Compound class: Synthetic organic
Comment: Cenisertib is an Aurora kinase A/B inhibitor that was developed for anti-cancer potential [1]. We show the compound with chirality as specified by the IUPAC name submitted to the WHO for INN registration. It is compound 60a as claimed in patent WO2005118544A2 [3].
Cenisertib has improved aqueous solubility compared to the dual inhibitor ABT-348 (ilorasertib). Preclinical anti-proliferative efficacy of cenisertib has been demonstrated in a wide range of xenograft models [4] and cell lines [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 99.41
Molecular weight 451.25
XLogP 2.35
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCN(CC1)c1ccc(cc1C)Nc1ncc(c(n1)NC1C2C=CC(C1C(=O)N)C2)F
Isomeric SMILES CN1CCN(CC1)c1ccc(cc1C)Nc1ncc(c(n1)N[C@@H]1[C@H]2C=C[C@@H]([C@@H]1C(=O)N)C2)F
InChI InChI=1S/C24H30FN7O/c1-14-11-17(5-6-19(14)32-9-7-31(2)8-10-32)28-24-27-13-18(25)23(30-24)29-21-16-4-3-15(12-16)20(21)22(26)33/h3-6,11,13,15-16,20-21H,7-10,12H2,1-2H3,(H2,26,33)(H2,27,28,29,30)/t15-,16+,20+,21-/m1/s1
1. Curtin ML, Heyman HR, Frey RR, Marcotte PA, Glaser KB, Jankowski JR, Magoc TJ, Albert DH, Olson AM, Reuter DR et al.. (2012)
Pyrazole diaminopyrimidines as dual inhibitors of KDR and Aurora B kinases.
Bioorg Med Chem Lett, 22 (14): 4750-5. [PMID:22695126]
2. Illert AL, Seitz AK, Rummelt C, Kreutmair S, Engh RA, Goodstal S, Peschel C, Duyster J, von Bubnoff N. (2014)
Inhibition of Aurora kinase B is important for biologic activity of the dual inhibitors of BCR-ABL and Aurora kinases R763/AS703569 and PHA-739358 in BCR-ABL transformed cells.
PLoS ONE, 9 (11): e112318. [PMID:25426931]
3. Li H, Argade A, Singh R, Thota S, Carroll D, Tso K, Taylor V, Mclaughlin J, Markovstov VMV. (2005)
Cycloalkyl substituted pyrimidinediamine compounds and their uses.
Patent number: WO2005118544A2. Assignee: Rigel Pharmaceuticals, Inc.. Priority date: 18/05/2004. Publication date: 15/12/2005.
4. McLaughlin J, Markovtsov V, Li H, Wong S, Gelman M, Zhu Y, Franci C, Lang D, Pali E, Lasaga J et al.. (2010)
Preclinical characterization of Aurora kinase inhibitor R763/AS703569 identified through an image-based phenotypic screen.
J Cancer Res Clin Oncol, 136 (1): 99-113. [PMID:19609559]