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
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1979), UK (1988))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
4-(4-aminophenyl)sulfonylaniline
International Nonproprietary Names Click here for help
INN number INN
1676 dapsone
Synonyms Click here for help
Aczone® | NSC-6091
Database Links Click here for help
BindingDB Ligand 50029764
CAS Registry No. 80-08-0 (source: PubChem)
ChEMBL Ligand CHEMBL1043
DrugBank Ligand DB00250
GtoPdb PubChem SID 405560375
PubChem CID 2955
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