SULFADIAZINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
SSD
Status
Molecule Category Free-form
ATC J01EC02
UNII 0N7609K889
EPA CompTox DTXSID7044130

Structure

InChI Key SEEPANYCNGTZFQ-UHFFFAOYSA-N
Smiles Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1
InChI
InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H10N4O2S
Molecular Weight 250.28
AlogP 0.86
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 97.97
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Bacterial dihydropteroate synthase inhibitor INHIBITOR PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase AUR family
- 21000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 74
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Compound was tested for the inhibition of malate dehydrogenase (MDH) at 200 uM None 5.0 %
Zone of inhibition of Escherichia coli at compound concentration of 40 mg/mL Escherichia coli 8.5 mm
Zone of inhibition of Escherichia coli at compound concentration of 80 mg/mL Escherichia coli 9.5 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 40 mg/mL Bacillus subtilis 8.5 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 80 mg/mL Bacillus subtilis 9.5 mm
Zone of inhibition of Escherichia coli at compound concentration of 160 mg/mL Escherichia coli 12.5 mm
Zone of inhibition of Salmonella typhae at compound concentration of 40 mg/mL Salmonella enterica subsp. enterica serovar Typhi 7.0 mm
Zone of inhibition of Salmonella typhae at compound concentration of 80 mg/mL Salmonella enterica subsp. enterica serovar Typhi 7.5 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 160 mg/mL Bacillus subtilis 13.5 mm
Zone of inhibition of Salmonella typhae at compound concentration of 160 mg/mL Salmonella enterica subsp. enterica serovar Typhi 9.0 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 40 mg/mL Klebsiella pneumoniae 12.5 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 80 mg/mL Klebsiella pneumoniae 13.5 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 40 mg/mL Staphylococcus aureus 7.0 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 80 mg/mL Staphylococcus aureus 7.5 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 160 mg/mL Klebsiella pneumoniae 15.0 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 160 mg/mL Staphylococcus aureus 9.5 mm
Inhibition of human CYP2C9 assessed as (S)-Flurbiprofen hydroxylation Homo sapiens -17.1 %
Antimicrobial activity against Toxoplasma gondii ENT harboring DHPS Ex2, E474D/Ex3, 156 sil Leu/Ex4, R560K/Ex5, 580 sil Gly/A597E/627 sil Glu mutant gene and DHFR Ex3, 156 sil Leu mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 4.28 ug.mL-1
Antimicrobial activity against Toxoplasma gondii B1 harboring DHPS Ex2, E474D/Ex4, R560K/Ex5, 580 sil Gly/ A597E/627 sil Glu mutant gene and DHFR Ex3, 156 sil Leu mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 50.0 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate RMS-1995-ABE harboring DHPS Ex5, A587V mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 50.0 ug.mL-1
Antimicrobial activity against Toxoplasma gondii ME49 infected in human MRC-5 cells infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 6.55 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate TRS-2004-REV infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 6.26 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate TOU-1998-TRI infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 2.95 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate RMS-2005-HAG infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 6.7 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate GRE-1995-MAE infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 14.95 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate PSP-2005-MUP infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 18.8 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate GRE-1998-TRA infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 16.85 ug.mL-1
Antimicrobial activity against Toxoplasma gondii NED infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 9.25 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate RMS-1994-LEF harboring DHPS Ex2, E474D/Ex4, R560K/Ex5, 580 sil Gly; A597E/627 sil Glu mutant gene and DHFR Ex3, 204 sil Ala mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 9.65 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate RMS-2003-DJO infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 4.9 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate RMS-2001-MAU infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 50.0 ug.mL-1
Antimicrobial activity against Toxoplasma gondii isolate GUY-2003-MEL harboring DHPS Ex2, E474D/Ex4, R560K/Ex5, 580 sil Gly/ A597E/627 sil Glu mutant gene and DHFR Ex2, 145 sil Val mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii 5.35 ug.mL-1
Antimicrobial activity against Toxoplasma gondii RH harboring DHPS Ex2, E474D/Ex4, R560K/Ex5, 580 sil Gly; A597E/627 sil Glu mutant gene and DHFR Ex3, 156 sil Leu mutant gene infected in human MRC-5 cells after 72 hrs by ELISA Toxoplasma gondii RH 6.52 ug.mL-1
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.81 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 74.08 %
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 -3.32 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.43 %
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 -0.11 % 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 -0.11 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Bangladesch
Croatia
Czech Republic
Germany
Hungary
Romania
Slovakia
Vietnam

Cross References

Resources Reference
ChEBI 9328
ChEMBL CHEMBL439
DrugBank DB00359
DrugCentral 2500
FDA SRS 0N7609K889
Human Metabolome Database HMDB0014503
KEGG C07658
PharmGKB PA451539
PubChem 5215
SureChEMBL SCHEMBL24176
ZINC ZINC000000120319
CONTENTS