naphthoquine   Click here for help

GtoPdb Ligand ID: 10396

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Naphthoquine is a 4-aminoquinoline antimalarial compound.
The marketed formulations contain naphthoquine phosphate (PubChem CID 9851774).

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 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 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 57.18
Molecular weight 409.19
XLogP 5.83
No. Lipinski's rules broken 1

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 Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
Isomeric SMILES Clc1ccc2c(c1)nccc2Nc1cc(CNC(C)(C)C)c(c2c1CCCC2)O
InChI InChI=1S/C24H28ClN3O/c1-24(2,3)27-14-15-12-22(17-6-4-5-7-18(17)23(15)29)28-20-10-11-26-21-13-16(25)8-9-19(20)21/h8-13,27,29H,4-7,14H2,1-3H3,(H,26,28)
InChI Key VEVMYTDOWUQLGI-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/)
No information available.
Summary of Clinical Use Click here for help
Naphthoquine does not have FDA or EMA approval but in combination with artemisinin (trade name ARCO®) is one of the new artemisinin-based combination therapies (ACTs) registered and used in a number of countries but not yet recommended by the WHO [4]. A Phase 4 trial to evaluate ARCO® for the treatment of uncomplicated P. falciparum malaria in adults and children has been completed (NCT01930331).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01930331 Safety, Tolerability, Pharmacokinetics and Efficacy of ARCO Phase 4 Interventional Ifakara Health Institute