dapsone   Click here for help

GtoPdb Ligand ID: 10934

Synonyms: Aczone® | NSC-6091
Approved drug Antimalarial Ligand
dapsone is an approved drug (FDA (1979), UK (1988))
Compound class: Synthetic organic
Comment: Dapsone is a sulfonamide-related antibacterial, antimalarial and anti-inflammatory drug. In bacteria it inhibits dihydropteroate synthase-mediated production of folic acid, which has the effect of disrupting the availability of thymidylate for DNA synthesis.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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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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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 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 94.56
Molecular weight 248.06
XLogP 0.86
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 Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
Isomeric SMILES Nc1ccc(cc1)S(=O)(=O)c1ccc(cc1)N
InChI InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChI Key MQJKPEGWNLWLTK-UHFFFAOYSA-N
Guide to Malaria Pharmacology Comments
Dapsone was used by the US Army during the Vietnam War as a prophylactic agent for malaria but was subsequently replaced by mefloquine [1]. The spread of Plasmodium strains resistant to existing antimalarial drugs, led to the introduction of a combination therapy containing chlorproguanil and dapsone (marketed as LapDap™). This formulation was withdrawn in 2008 following concerns about haemolytic anaemia in patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency [2]. A combined prophylactic medicine with pyrimethamine (Maloprim®) has also been withdrawn in many jurisdictions [4].

Potential Target/Mechanism Of Action: dapsone is an inhibitor of P. falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase (PfPPPK-DHPS) [6].