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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Search Google for chemical match using the InChIKey HMABYWSNWIZPAG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HMABYWSNWIZPAG
Search PubMed clinical trials rucaparib
Search PubMed titles rucaparib
Search PubMed titles/abstracts rucaparib
SynPHARM 80263 (in complex with poly(ADP-ribose) polymerase 1)
UniChem Compound Search for chemical match using the InChIKey HMABYWSNWIZPAG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HMABYWSNWIZPAG-UHFFFAOYSA-N
Wikipedia Rucaparib