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
SMILES / InChI / InChIKey
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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)
InChI Key HMABYWSNWIZPAG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2016), EMA (2018))
International Nonproprietary Names Click here for help
INN number INN
9471 rucaparib
Synonyms Click here for help
AG-014699 | AG014699 | AG14447 | PF-01367338 | Rubraca®
Database Links Click here for help
CAS Registry No. 283173-50-2
ChEMBL Ligand CHEMBL1173055
DrugCentral Ligand 5203
GtoPdb PubChem SID 223366069
PubChem CID 9931954
RCSB PDB Ligand RPB
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SynPHARM 80263 (in complex with poly(ADP-ribose) polymerase 1)
Wikipedia Rucaparib