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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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 1
Rotatable bonds 7
Topological polar surface area 28.16
Molecular weight 433.1
XLogP 2.62
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 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;
InChI Key IRJOHJGUSPNBRI-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Ferroquine is in clinical development as a combination therapy and with potential as a single-dose treatment for P. falciparum malaria including resistant strains.

Potential Target/Mechanism Of Action: As the precise mechanism of action of ferroquine is not yet known, we do not have a molecular target for this compound. Further information about possible mechanistic insights is provided under the Clinical data tab.
Target Candidate Profiles
Profile Intended Use Target Stage Comment References
TCP-1 reduce parasite burden asexual blood stages