palacaparib   Click here for help

GtoPdb Ligand ID: 11946

Synonyms: AZD-9574 | AZD9574 | example 20 [WO2021260092A1] | TQB3823
PDB Ligand
Compound class: Synthetic organic
Comment: AZD9574 is a CNS penetrant PARP1 selective inhibitor. Its structure was revealed during the 'first disclosure' session at the ACS Spring 2022 meeting. It was reported that it had shown efficacy in an intracranial BRCA1m MDA-MB-436 xenograft model. AZD9574's chemical structure is claimed in AstraZeneca's patent WO2021260092A1 [1] and its substructure is very similar to the published non-CNS penetrant PARP1 selective inhibitor saruparib, but with a couple of methyl groups substituted by fluorines.
The chemical structure of AZD9574 is identical to that for the INN palacaparib (proposed list 132, Feb. 2025).
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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

palacaparib is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 94.22
Molecular weight 428.18
XLogP 1.66
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CNC(=O)c1ccc(c(n1)F)N1CCN(CC1)Cc1ccc2c(c1F)[nH]c(=O)c(n2)C
Isomeric SMILES CNC(=O)c1nc(F)c(cc1)N1CCN(Cc2c(F)c3c(cc2)nc(C)c(=O)[nH]3)CC1
InChI InChI=1S/C21H22F2N6O2/c1-12-20(30)27-18-14(25-12)4-3-13(17(18)22)11-28-7-9-29(10-8-28)16-6-5-15(21(31)24-2)26-19(16)23/h3-6H,7-11H2,1-2H3,(H,24,31)(H,27,30)
InChI Key WXRCLFFPZXJCLS-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-fluoro-5-[4-[(5-fluoro-2-methyl-3-oxo-4H-quinoxalin-6-yl)methyl]piperazin-1-yl]-N-methylpyridine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
13369 palacaparib
Synonyms Click here for help
AZD-9574 | AZD9574 | example 20 [WO2021260092A1] | TQB3823
Database Links Click here for help
CAS Registry No. 2756333-39-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL5095223
GtoPdb PubChem SID 461663501
PubChem CID 162524593
RCSB PDB Ligand A1H64
Search Google for chemical match using the InChIKey WXRCLFFPZXJCLS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WXRCLFFPZXJCLS
Search PubMed clinical trials palacaparib
Search PubMed titles palacaparib
Search PubMed titles/abstracts palacaparib
UniChem Compound Search for chemical match using the InChIKey WXRCLFFPZXJCLS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WXRCLFFPZXJCLS-UHFFFAOYSA-N

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MedChemExpress
AZD-9574 (links to external site)
Cat. No. HY-145804