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nitroxoline   Click here for help

GtoPdb Ligand ID: 13964

Synonyms: APL-1202 | APL1202 | compound 10 [PMID: 30939017]
Approved drug PDB Ligand
nitroxoline is an approved drug
Compound class: Synthetic organic
Comment: Nitroxoline is an antimicrobial used to treat urinary tract infections [3]. Repurposing of nitroxoline for infectious diseases and oncological indications has been proposed, although pharmacokinetic challenges are likely to hamper clinical translation.

From a patent it would appear that Healx Ltd. are interested in pursuing nitroxoline for the treatment of plexiform neurofibroma/neurofibromatosis type 1 (NF1) [1]. Review of Healx's active pipeline (January 2026) reveals two candidates with codes HLX-1502 and HLX-0213 in development for NF1 [4]. HLX-1502 has reached phase 2 whereas HLX-0213 is in the discovery phase (at time of writing), so it is plausible that HLX-1502 is nitroxoline. We await formal disclosure of this potential association.
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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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Click here for structure editor
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 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 75.73
Molecular weight 190.16
XLogP 0.8
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 C1=CN=C2C(=C1)C(=CC=C2O)[N+](=O)[O-]
Isomeric SMILES C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
InChI InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
InChI Key RJIWZDNTCBHXAL-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
Approved drug? Yes.
IUPAC Name Click here for help
5-nitroquinolin-8-ol
International Nonproprietary Names Click here for help
INN number INN
1833 nitroxoline
Synonyms Click here for help
APL-1202 | APL1202 | compound 10 [PMID: 30939017]
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nitroxoline
Other databases
CAS Registry No. 4008-48-4 (source: Scifinder)
ChEBI CHEBI:67121
ChEMBL Ligand CHEMBL1454910
DrugBank Ligand DB01422
DrugCentral Ligand 1954
GtoPdb PubChem SID 518520591
PubChem CID 19910
RCSB PDB Ligand HNQ
Search Google for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RJIWZDNTCBHXAL
Search PubMed clinical trials nitroxoline
Search PubMed titles nitroxoline
Search PubMed titles/abstracts nitroxoline
UniChem Compound Search for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RJIWZDNTCBHXAL-UHFFFAOYSA-N