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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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 Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
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
Specialist databases
GPCRdb Ligand dapsone
Other databases
BindingDB Ligand 50029764
CAS Registry No. 80-08-0 (source: PubChem)
ChEMBL Ligand CHEMBL1043
DrugBank Ligand DB00250
DrugCentral Ligand 782
GtoPdb PubChem SID 405560375
PubChem CID 2955
Search Google for chemical match using the InChIKey MQJKPEGWNLWLTK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MQJKPEGWNLWLTK
Search PubMed clinical trials dapsone
Search PubMed titles dapsone
Search PubMed titles/abstracts dapsone
UniChem Compound Search for chemical match using the InChIKey MQJKPEGWNLWLTK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MQJKPEGWNLWLTK-UHFFFAOYSA-N