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
References
1. Barr J. (2011)
A short history of dapsone, or an alternative model of drug development.
J Hist Med Allied Sci, 66 (4): 425-67. [PMID:20966036]
2. Luzzatto L. (2010)
The rise and fall of the antimalarial Lapdap: a lesson in pharmacogenetics.
Lancet, 376 (9742): 739-41. [PMID:20599264]
3. Petersen E. (2004)
Malaria chemoprophylaxis: when should we use it and what are the options?.
Expert Rev Anti Infect Ther, 2 (1): 119-32. [PMID:15482177]
4. Queener SF. (1995)
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
J Med Chem, 38 (24): 4739-59. [PMID:7490723]
5. Zhang Y, Meshnick SR. (1991)
Inhibition of Plasmodium falciparum dihydropteroate synthetase and growth in vitro by sulfa drugs.
Antimicrob Agents Chemother, 35 (2): 267-71. [PMID:2024960]