probenecid   Click here for help

GtoPdb Ligand ID: 4357

Synonyms: Probalan®
Approved drug PDB Ligand
probenecid is an approved drug (FDA (1951))
Compound class: Synthetic organic
Comment: Probenecid is considered to be the prototypical uricosuric agent.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 83.06
Molecular weight 285.1
XLogP 2.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O)CCC
Isomeric SMILES CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O)CCC
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)
InChI Key DBABZHXKTCFAPX-UHFFFAOYSA-N
Bioactivity Comments
Competitive inhibition by probenecid has been demonstrated at OAT1, OAT2, OAT3, OAT4, OAT5 [5,8,11,14], and URAT1 [13]. Furthermore, inhibition by probenecid has also been demonstrated at MRP1, MRP2, MRP3, MRP4 and MRP5 [1,4,6,9,12].
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Sodium/phosphate cotransporter 1 3
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R38 Hs Antagonist Antagonist 3.7 pIC50 - 7
pIC50 3.7 (IC50 2.11x10-4 M) [7]
TAS2R16 Hs Antagonist Antagonist 3.5 pIC50 - 7
pIC50 3.5 (IC50 2.92x10-4 M) [7]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPV2 Rn Activator Activation 4.5 pEC50 - 2
pEC50 4.5 (EC50 3.19x10-5 M) [2]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Organic anion transporter 1 Primary target of this compound Hs Inhibitor Inhibition 4.9 pIC50 - 10
pIC50 4.9 (IC50 1.25x10-5 M) Inhibition of urate transport by human SCL22A6. [10]
OATP1C1 Hs Inhibitor Inhibition - - -