PROBENECID

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC M04AB01
UNII PO572Z7917
EPA CompTox DTXSID9021188

Structure

InChI Key DBABZHXKTCFAPX-UHFFFAOYSA-N
Smiles CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1
InChI
InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H19NO4S
Molecular Weight 285.36
AlogP 2.2
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 74.68
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Solute carrier family 22 member 11 inhibitor INHIBITOR PubMed PubMed PubMed PubMed Wikipedia
Protein: Solute carrier family 22 member 6
Description: Solute carrier family 22 member 6
Organism : Homo sapiens
Q4U2R8 ENSG00000197901
Protein: Solute carrier family 22 member 8
Description: Organic anion transporter 3
Organism : Homo sapiens
Q8TCC7 ENSG00000149452
Protein: Solute carrier family 22 member 11
Description: Solute carrier family 22 member 11
Organism : Homo sapiens
Q9NSA0 ENSG00000168065
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Lyase
- - - 1245-1245 -
Enzyme Transferase
- - - 96000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22-89
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 15000-86390 - 6310-6400 30-36
Assay Description Organism Bioactivity Reference
Inhibition of human URAT1-mediated urate uptake in HEK293 cells at 2 uM Homo sapiens 30.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -8.9 %
Inhibition of human URAT1 expressed in xenopus oocyte assessed as inhibition of [14C]-labelled urate uptake at 50 uM after 60 mins by liquid scintillation counting Homo sapiens 35.7 %
TP_TRANSPORTER: inhibition of BSP uptake (BSP: 2 uM, Probenecid: 1000 uM) in Xenopus laevis oocytes Xenopus laevis 74.0 %
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 35.2 %
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 22.0 %
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 26.4 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 81.99 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 89.44 %
Inhibition of recombinant human carbonic anhydrase 2 after 15 mins by stopped flow CO2 hydration assay Homo sapiens 431.0 nM
Inhibition of recombinant human carbonic anhydrase 9 after 15 mins by stopped flow CO2 hydration assay Homo sapiens 360.0 nM
Inhibition of OAT3 (unknown origin) expressed in HEK293 cells assessed as reduction of [3H]E-sul substrate uptake at 100 uM by liquid scintillation counting Homo sapiens 88.5 %
Inhibition of OAT1 (unknown origin) expressed in HEK293 cells assessed as reduction of [3H]PAH substrate uptake at 300 uM by liquid scintillation counting Homo sapiens 96.2 %
Inhibition of OAT4 (unknown origin) expressed in HEK293 cells assessed as reduction of [3H]E-sul substrate uptake at 500 uM by liquid scintillation counting Homo sapiens 81.4 %
Inhibition of human carbonic anhydrase 2 by stopped-flow CO2 hydrase assay Homo sapiens 431.0 nM
Inhibition of human carbonic anhydrase 9 by stopped-flow CO2 hydrase assay Homo sapiens 360.0 nM
Inhibition of human carbonic anhydrase-2 incubated for 15 mins by stopped-flow CO2 hydration assay Homo sapiens 431.0 nM
Inhibition of human carbonic anhydrase-9 incubated for 15 mins by stopped-flow CO2 hydration assay Homo sapiens 360.0 nM
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 13.34 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 1.2 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 16.52 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 19.93 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 30.42 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.37 %
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 -7.72 %
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 1.35 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.12 %
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 0.08 % 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 %

Cross References

Resources Reference
ChEBI 8426
ChEMBL CHEMBL897
DrugBank DB01032
DrugCentral 2268
FDA SRS PO572Z7917
Human Metabolome Database HMDB0015166
Guide to Pharmacology 4357
KEGG C07372
PharmGKB PA451106
PubChem 4911
SureChEMBL SCHEMBL3663
ZINC ZINC000000001982
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