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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2D Structure
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Physico-chemical Properties
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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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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 This formulation was withdrawn in 2008 following concerns about haemolytic anaemia in patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency [2]. A combined prophylactic medicine with pyrimethamine (Maloprim®) has also been withdrawn in many jurisdictions [3].

Potential Target/Mechanism Of Action: dapsone is an inhibitor of P. falciparum hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase (PfPPPK-DHPS) [5].