NALIDIXIC ACID

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J01MB02
UNII 3B91HWA56M
EPA CompTox DTXSID3020912

Structure

InChI Key MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Smiles CCn1cc(C(=O)O)c(=O)c2ccc(C)nc21
InChI
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H12N2O3
Molecular Weight 232.24
AlogP 1.42
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 72.19
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Bacterial DNA gyrase inhibitor INHIBITOR FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - -
Enzyme Isomerase
- 100000 - - -
Enzyme Oxidoreductase
- - - - 34
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 63
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 57500 - - -
Assay Description Organism Bioactivity Reference
Inhibition of DNA gyrase supercoiling in Escherichia coli. Escherichia coli 52.0 ug.mL-1
Inhibitory concentration in supercoiling inhibition Escherichia coli DNA gyrase assay Escherichia coli 100.0 ug.mL-1
In vitro antibacterial activity was determined as inhibitory concentration causing 50% DNA-gyrase supercoiling inhibition (SCI) Escherichia coli 52.0 ug.mL-1
Inhibition of supercoiling activity of DNA gyrase in Escherichia coli Escherichia coli 52.0 ug.mL-1
Percent inhibition of filarial parasite Setaria cervi by compound at 10 ug/mL concentration Setaria cervi 20.0 %
Percent inhibition of filarial parasite Setaria cervi by compound at 20 ug/mL concentration Setaria cervi 40.0 %
Percent inhibition of filarial parasite Setaria cervi by compound at 40 ug/mL concentration Setaria cervi 80.0 %
Inhibition of Bacillus subtilis topoisomerase4 activity Bacillus subtilis 34.6 ug.mL-1
Inhibition of Bacillus subtilis gyrase activity Bacillus subtilis 276.0 ug.mL-1
Inhibition of Mycobacterium leprae recombinant DNA gyrase expressed in Escherichia coli assessed as inhibition of pBR322 DNA supercoiling Mycobacterium leprae 300.0 ug.mL-1
Inhibition of Mycobacterium leprae wild type DNA gyrase A2B2 assessed as DNA supercoiling inhibition Mycobacterium leprae 300.0 ug.mL-1
Inhibition of Mycobacterium leprae DNA gyrase subunit A G89C mutant assessed as DNA supercoiling inhibition Mycobacterium leprae 150.0 ug.mL-1
Inhibition of Mycobacterium leprae DNA gyrase subunit A A91V mutant assessed as DNA supercoiling inhibition Mycobacterium leprae 170.0 ug.mL-1
Inhibition of Mycobacterium leprae wild type DNA gyrase subunit B D205N mutant assessed as DNA supercoiling inhibition Mycobacterium leprae 600.0 ug.mL-1
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Nalidixate; 2000 uM) in Xenopus laevis oocytes Xenopus laevis 85.0 %
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method Electrophorus electricus 0.82 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method Equus caballus -8.73 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 63.37 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 81.71 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control Homo sapiens 88.0 %
Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control Homo sapiens 34.0 %
Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 after 5 days by micro alamar blue assay Mycobacterium tuberculosis H37Rv 63.0 %
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 -0.44 %
Inhibition of Escherichia coli DNA gyrase super-coiling activity using pBR322 DNA as substrate after 30 mins by fluorescence assay Escherichia coli 1.74 ug.mL-1
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.92 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.78 %
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 -0.05 % 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 0.12 % 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 0.12 % 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 -0.05 %

Cross References

Resources Reference
ChEBI 100147
ChEMBL CHEMBL5
DrugBank DB00779
DrugCentral 1875
FDA SRS 3B91HWA56M
Human Metabolome Database HMDB0014917
KEGG C05079
PDB NIX
PharmGKB PA164746384
PubChem 4421
SureChEMBL SCHEMBL21736
ZINC ZINC000000057421
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