pilaralisib   Click here for help

GtoPdb Ligand ID: 7963

Synonyms: SAR-245408 | XL-147 | XL147
Compound class: Synthetic organic
Comment: Pilaralisib is an orally bioavailable small molecule inhibitor of the class I phosphatidylinositol 3 kinase (PI3K) family of lipid kinases, with potential antineoplastic activity [1-2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 146.38
Molecular weight 448.08
XLogP 4.95
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cc1ccc(cc1)S(=O)(=O)Nc1nc2ccccc2nc1Nc1ccc2c(c1)nsn2
Isomeric SMILES Cc1ccc(cc1)S(=O)(=O)Nc1nc2ccccc2nc1Nc1ccc2c(c1)nsn2
InChI InChI=1S/C21H16N6O2S2/c1-13-6-9-15(10-7-13)31(28,29)27-21-20(23-16-4-2-3-5-17(16)24-21)22-14-8-11-18-19(12-14)26-30-25-18/h2-12H,1H3,(H,22,23)(H,24,27)
InChI Key MQMKRQLTIWPEDM-UHFFFAOYSA-N
References
1. Chakrabarty A, Sánchez V, Kuba MG, Rinehart C, Arteaga CL. (2012)
Feedback upregulation of HER3 (ErbB3) expression and activity attenuates antitumor effect of PI3K inhibitors.
Proc. Natl. Acad. Sci. U.S.A., 109 (8): 2718-23. [PMID:21368164]
2. Shapiro GI, Rodon J, Bedell C, Kwak EL, Baselga J, Braña I, Pandya SS, Scheffold C, Laird AD, Nguyen LT et al.. (2014)
Phase I safety, pharmacokinetic, and pharmacodynamic study of SAR245408 (XL147), an oral pan-class I PI3K inhibitor, in patients with advanced solid tumors.
Clin. Cancer Res., 20 (1): 233-45. [PMID:24166903]
3. Wu P, Hu Y. (2012)
Small molecules targeting phosphoinositide 3-kinases.
Medchemcomm, 3 (11): 1337-1355. DOI: 10.1039/C2MD20044A