ferroquine   Click here for help

GtoPdb Ligand ID: 9972

Synonyms: SSR97193
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Ferroquine is a 4-aminoquinoline antimalarial compound with a novel ferrocenic group in its side chain.
The ferrocenic group causes rendering problems, with different images of the chemical structure found across web resources. We show the structure provided by NIH US National Library of Medicine (InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N). PubChem provide a different InChIKey DLYPREQTTOHKSM-UHFFFAOYSA-N with two structural representations PubChem CID 56841801 (link in table below) and PubChem CID 76419023.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 28.16
Molecular weight 433.1
XLogP 2.62
No. Lipinski's rules broken 0
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Canonical SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
Isomeric SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
InChI InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h4,6-10H,5,11-12H2,1-2H3,(H,20,21);1-3H,4H2;
No information available.
Summary of Clinical Use Click here for help
Recruitment has commenced for a Phase 2 trial to evaluate single dose combination therapy with artefenomel for the treatment of uncomplicated P. falciparum malaria in adults and children (NCT02497612).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Ferroquine is thought to have a similar similar mechanisms of action to chloroquine, with both molecules exerting their action by interfering with the process of detoxification of heme by the parasite [2].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02497612 To Evaluate the Efficacy of a Single Dose Regimen of Ferroquine and Artefenomel in Adults and Children With Uncomplicated Plasmodium Falciparum Malaria Phase 2 Interventional Sanofi