probenecid   Click here for help

GtoPdb Ligand ID: 4357

Synonyms: Probalan®
Approved drug
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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View more information in the IUPHAR Pharmacology Education Project: probenecid

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
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Summary of Clinical Use Click here for help
Probenecid is used to reduce serum uric acid levels in patients with chronic gout.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Probenecid acts to inhibit the renal excretion of organic anions and in addition, reduces tubular reabsorption of urate. This is likely to occur as a result of inhibition of urate transport by organic anion transporters such as SLC22A6 (OAT1).
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