DAPSONE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC D10AX05 J04BA02
UNII 8W5C518302
EPA CompTox DTXSID4020371

Structure

InChI Key MQJKPEGWNLWLTK-UHFFFAOYSA-N
Smiles Nc1ccc(S(=O)(=O)c2ccc(N)cc2)cc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H12N2O2S
Molecular Weight 248.31
AlogP 1.68
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 86.18
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Dihydropteroate synthase 1 inhibitor INHIBITOR ISBN PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase
- 12410 - - -
Enzyme Oxidoreductase
- 1500 - - 11
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 183 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 78
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 11.0 %
Antinephritic activity on chronic graft-versus-host disease (GVHD) in mice at 10 mg/kg p.o. Mus musculus 50.0 %
Antinephritic activity on chronic graft-versus-host disease (GVHD) in mice at 32 mg/kg p.o. Mus musculus 50.0 %
Inhibition of proteinuria in the graft-versus-host disease mice following 100 mg/kg p.o. administration. Mus musculus 95.0 %
In vitro antimalarial activity against Plasmodium falciparum D6 after 72 hrs in SYBR green fluorescence assay Plasmodium falciparum 0.0031 ug.mL-1
In vitro antimalarial activity against Plasmodium falciparum W2 after 72 hrs in SYBR green fluorescence assay Plasmodium falciparum 0.1562 ug.mL-1
In vitro antimalarial activity against Plasmodium falciparum D6 after 72 hrs in SYBR green fluorescence assay Plasmodium falciparum 0.0102 ug.mL-1
In vitro antimalarial activity against Plasmodium falciparum W2 after 72 hrs in SYBR green fluorescence assay Plasmodium falciparum 0.2416 ug.mL-1
Antimalarial activity against Plasmodium falciparum D6 as reduced [3H]hypoxanthine uptake after 72 hrs Plasmodium falciparum 0.0029 ug.mL-1
Antimalarial activity against Plasmodium falciparum W2 as reduced [3H]hypoxanthine uptake after 72 hrs Plasmodium falciparum 0.1241 ug.mL-1
Antagonist activity at recombinant human 5-HT6 receptor expressed in HEK293 cells assessed as 5-HT-induced intracellular cAMP production after 30 mins Homo sapiens 183.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 78.21 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 84.17 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -0.58 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 0.96 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 5.01 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.27 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 2.33 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans -0.53 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 0.91 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -2.39 %
Inhibition of MPO (unknown origin) Homo sapiens 420.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.43 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control Mycobacterium leprae 92.0 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 20 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control Mycobacterium leprae 91.0 %

Cross References

Resources Reference
ChEBI 4325
ChEMBL CHEMBL1043
DrugBank DB00250
DrugCentral 782
FDA SRS 8W5C518302
Human Metabolome Database HMDB0014395
Guide to Pharmacology 10934
KEGG C07666
PharmGKB PA449211
PubChem 2955
SureChEMBL SCHEMBL21428
ZINC ZINC000000006310
CONTENTS