rucaparib   Click here for help

GtoPdb Ligand ID: 7736

Synonyms: AG-014699 | AG014699 | AG14447 | PF-01367338 | Rubraca®
Approved drug PDB Ligand
rucaparib is an approved drug (FDA (2016), EMA (2018))
Compound class: Synthetic organic
Comment: Rucaparib is an orally active poly(ADP-ribose)polymerase (PARP) inhibitor with anti-cancer activity [7]. It was developed by Clovis Oncology.
PARP inhibitors are known to enhance efficacy of anti-cancer therapies such as DNA alkylating agents, topoisomerase I poisons, and ionizing radiation.
Note that in the Thomas et al. paper [7], AG014699 refers to the phosphate salt and AG14447 to the parent molecule.
Rucaparib was accepted for FDA priority review for the treatment of advanced ovarian cancer harbouring mutant BRCA (August 2016).
Note: olaparib was the first PARP inhibitor to be approved for clinical use.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 56.92
Molecular weight 323.14
XLogP 3.25
No. Lipinski's rules broken 0
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Canonical SMILES CNCc1ccc(cc1)c1[nH]c2c3c1CCNC(=O)c3cc(c2)F
Isomeric SMILES CNCc1ccc(cc1)c1[nH]c2c3c1CCNC(=O)c3cc(c2)F
InChI InChI=1S/C19H18FN3O/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24)
Bioactivity Comments
Note that some bioactivity data may be associated with the phosphate salt, PubChem CID 9931953.
Rucaparib sensitises cells to chemotherapy drugs and radiotherapy, when given alongside these anti-cancer therapies. As a single agent it shows no toxicity [7].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
poly(ADP-ribose) polymerase 1 Primary target of this compound Hs Inhibitor Inhibition 8.9 pKi - 7
pKi 8.9 (Ki 1.4x10-9 M) [7]