SULFAMETHOXAZOLE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J01EC01
UNII JE42381TNV
EPA CompTox DTXSID8026064

Structure

InChI Key JLKIGFTWXXRPMT-UHFFFAOYSA-N
Smiles Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1
InChI
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H11N3O3S
Molecular Weight 253.28
AlogP 1.37
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 98.22
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Bacterial dihydropteroate synthase inhibitor INHIBITOR 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 Oxidoreductase
- 100 - - -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
- - 577 10 -
Enzyme Transferase
- 4700 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
- 4000-4000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 104
Assay Description Organism Bioactivity Reference
Inhibitory activity against dihydrofolate reductase in Pneumocystis carinii in the prence of 100 micro M PABA. Pneumocystis carinii 100.0 nM
Binding affinity for human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 577.0 nM
Inhibition constant for human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 10.1 nM
Zone of inhibition of Escherichia coli at compound concentration of 40 mg/mL Escherichia coli 18.5 mm
Zone of inhibition of Escherichia coli at compound concentration of 80 mg/mL Escherichia coli 20.5 mm
Zone of inhibition of Escherichia coli at compound concentration of 160 mg/mL Escherichia coli 22.5 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 40 mg/mL Bacillus subtilis 15.5 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 80 mg/mL Bacillus subtilis 18.5 mm
Zone of inhibition of Salmonella typhae at compound concentration of 40 mg/mL Salmonella enterica subsp. enterica serovar Typhi 8.5 mm
Zone of inhibition of Salmonella typhae at compound concentration of 80 mg/mL Salmonella enterica subsp. enterica serovar Typhi 9.0 mm
Zone of inhibition of Bacillus subtilis at compound concentration of 160 mg/mL Bacillus subtilis 20.0 mm
Zone of inhibition of Salmonella typhae at compound concentration of 160 mg/mL Salmonella enterica subsp. enterica serovar Typhi 12.5 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 40 mg/mL Klebsiella pneumoniae 8.5 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 80 mg/mL Klebsiella pneumoniae 9.0 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 40 mg/mL Staphylococcus aureus 19.5 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 80 mg/mL Staphylococcus aureus 20.5 mm
Zone of inhibition of Klebsiella pneumoniae at compound concentration of 160 mg/mL Klebsiella pneumoniae 11.5 mm
Zone of inhibition of Staphylococcus aureus at compound concentration of 160 mg/mL Staphylococcus aureus 21.0 mm
Inhibition of human CYP2C9 assessed as (S)-Flurbiprofen hydroxylation Homo sapiens -17.1 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 104.29 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 94.47 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
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 -14.52 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 28.59 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 4.09 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 6.86 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 6.61 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 6.42 %
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 2.83 %
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 18.96 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.05 %
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 -0.08 % 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 -0.08 %

Environmental Exposure

Environmental Exposure Map
Countries
Bangladesch
Croatia
Czech Republic
Germany
Hungary
India
Romania
Serbia
Slovakia
Slovenia
South Africa
USA
Vietnam

Cross References

Resources Reference
ChEBI 9332
ChEMBL CHEMBL443
DrugBank DB01015
DrugCentral 2514
FDA SRS JE42381TNV
Human Metabolome Database HMDB0015150
Guide to Pharmacology 10933
KEGG C07315
PDB 08D
PharmGKB PA451544
PubChem 5329
SureChEMBL SCHEMBL3656
ZINC ZINC000000089763
CONTENTS