FUROSEMIDE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C03CA01
UNII 7LXU5N7ZO5
EPA CompTox DTXSID6020648

Structure

InChI Key ZZUFCTLCJUWOSV-UHFFFAOYSA-N
Smiles NS(=O)(=O)c1cc(C(=O)O)c(NCc2ccco2)cc1Cl
InChI
InChI=1S/C12H11ClN2O5S/c13-9-5-10(15-6-7-2-1-3-20-7)8(12(16)17)4-11(9)21(14,18)19/h1-5,15H,6H2,(H,16,17)(H2,14,18,19)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H11ClN2O5S
Molecular Weight 330.75
AlogP 1.89
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 122.63
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Sodium-(potassium)-chloride cotransporter 2 inhibitor INHIBITOR DOI DailyMed Wikipedia Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Lyase
- - - 245 -
Enzyme Oxidoreductase
- 3760 - - 21
Enzyme Transferase
- 12700 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Carboxylic acid receptor Kynurenic acid receptor
6200-11200 - - 3270 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22-90
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 12
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 7
Unclassified protein
- 53460 - 2285 -
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Dose required for 50% inhibition of chloride transport in frog cornea was evaluated frog 64.0 uM
Inhibition of malate dehydrogenase (MDH) at 400 uM None 21.0 %
Percent inhibition of serum creatinine by the compound given as ratio of Cr value in treated to vehicle treated ones after intraperitoneal administration of 10 mg/kg of compound to rats(vehicle 3.22+/-0.35) Rattus norvegicus -30.0 %
Percent inhibition of Urea nitrogen by the compound given as ratio of UN value in treated to vehicle treated ones after intraperitoneal administration of 10 mg/kg of compound to rats(vehicle 110.7+/-9.4) Rattus norvegicus -36.0 %
Inhibitory activity against Bacillus subtilis AcpS by HTRF assay Bacillus subtilis 4.2 ug.mL-1
Inhibition of human recombinant full length CA1 by stopped-flow CO2 hydration method Homo sapiens 62.0 nM
Inhibition of human recombinant full length CA2 by stopped-flow CO2 hydration method Homo sapiens 65.0 nM
Inhibition of human recombinant full length CA4 by stopped-flow CO2 hydration method Homo sapiens 564.0 nM
Inhibition of human recombinant full length CA5A by stopped-flow CO2 hydration method Homo sapiens 499.0 nM
Inhibition of human recombinant full length CA5B by stopped-flow CO2 hydration method Homo sapiens 322.0 nM
Inhibition of human recombinant full length CA6 by stopped-flow CO2 hydration method Homo sapiens 245.0 nM
Inhibition of human recombinant full length CA7 by stopped-flow CO2 hydration method Homo sapiens 513.0 nM
Inhibition of human recombinant CA9 catalytic domain by stopped-flow CO2 hydration method Homo sapiens 420.0 nM
Inhibition of human recombinant CA12 catalytic domain by stopped-flow CO2 hydration method Homo sapiens 261.0 nM
Inhibition of mouse recombinant full length CA13 by stopped-flow CO2 hydration method Mus musculus 550.0 nM
Inhibition of human recombinant full length CA14 by stopped-flow CO2 hydration method Homo sapiens 52.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 11.7 %
Antagonist activity to dog NKCC1 transporter expressed in MDCK cells assessed as inhibition of Cl- free medium-stimulated Rb+ influx at 100 uM after 45 mins by atomic absorption spectroscopy Canis lupus familiaris 100.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 23.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 22.3 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 34.5 %
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 7.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 86.58 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.27 %
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 36.0 %
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 %
Reduction in Abeta oligomers levels in Tg2576 mouse administered for for 4 weeks Mus musculus 30.0 %
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 14.48 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.33 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 9.57 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 20.35 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 25.01 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.34 %
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 -7.53 %
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 23.42 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.33 %
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 -0.06 % 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 -0.06 %
Inhibition of human amyloid beta (1 to 42) fibrillization at 100 uM measured every 15 mins by Thioflavin-T fluorescence assay relative to control Homo sapiens 8.56 %

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Hungary
Romania
Serbia
Slovakia
Slovenia

Cross References

Resources Reference
ChEBI 47426
ChEMBL CHEMBL35
DrugBank DB00695
DrugCentral 1258
FDA SRS 7LXU5N7ZO5
Human Metabolome Database HMDB0001933
Guide to Pharmacology 4839
KEGG C07017
PDB FUN
PharmGKB PA449719
PubChem 3440
SureChEMBL SCHEMBL9811
ZINC ZINC000000035804
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