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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: probenecid

probenecid is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Bakos E, Evers R, Sinkó E, Váradi A, Borst P, Sarkadi B. (2000)
Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions.
Mol Pharmacol, 57 (4): 760-8. [PMID:10727523]
2. Bang S, Kim KY, Yoo S, Lee SH, Hwang SW. (2007)
Transient receptor potential V2 expressed in sensory neurons is activated by probenecid.
Neurosci Lett, 425 (2): 120-5. [PMID:17850966]
3. Busch AE, Schuster A, Waldegger S, Wagner CA, Zempel G, Broer S, Biber J, Murer H, Lang F. (1996)
Expression of a renal type I sodium/phosphate transporter (NaPi-1) induces a conductance in Xenopus oocytes permeable for organic and inorganic anions.
Proc Natl Acad Sci USA, 93 (11): 5347-51. [PMID:8643577]
4. Dallas S, Schlichter L, Bendayan R. (2004)
Multidrug resistance protein (MRP) 4- and MRP 5-mediated efflux of 9-(2-phosphonylmethoxyethyl)adenine by microglia.
J Pharmacol Exp Ther, 309 (3): 1221-9. [PMID:14762102]
5. Enomoto A, Takeda M, Shimoda M, Narikawa S, Kobayashi Y, Kobayashi Y, Yamamoto T, Sekine T, Cha SH, Niwa T et al.. (2002)
Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors.
J Pharmacol Exp Ther, 301 (3): 797-802. [PMID:12023506]
6. Gollapudi S, Kim CH, Tran BN, Sangha S, Gupta S. (1997)
Probenecid reverses multidrug resistance in multidrug resistance-associated protein-overexpressing HL60/AR and H69/AR cells but not in P-glycoprotein-overexpressing HL60/Tax and P388/ADR cells.
Cancer Chemother Pharmacol, 40 (2): 150-8. [PMID:9182837]
7. Greene TA, Alarcon S, Thomas A, Berdougo E, Doranz BJ, Breslin PA, Rucker JB. (2011)
Probenecid inhibits the human bitter taste receptor TAS2R16 and suppresses bitter perception of salicin.
PLoS One, 6 (5): e20123. [PMID:21629661]
8. Hagos FT, Daood MJ, Ocque JA, Nolin TD, Bayir H, Poloyac SM, Kochanek PM, Clark RS, Empey PE. (2017)
Probenecid, an organic anion transporter 1 and 3 inhibitor, increases plasma and brain exposure of N-acetylcysteine.
Xenobiotica, 47 (4): 346-353. [PMID:27278858]
9. Horikawa M, Kato Y, Tyson CA, Sugiyama Y. (2002)
The potential for an interaction between MRP2 (ABCC2) and various therapeutic agents: probenecid as a candidate inhibitor of the biliary excretion of irinotecan metabolites.
Drug Metab Pharmacokinet, 17 (1): 23-33. [PMID:15618649]
10. Ichida K, Hosoyamada M, Kimura H, Takeda M, Utsunomiya Y, Hosoya T, Endou H. (2003)
Urate transport via human PAH transporter hOAT1 and its gene structure.
Kidney Int, 63 (1): 143-55. [PMID:12472777]
11. Monien BH, Müller C, Bakhiya N, Donath C, Frank H, Seidel A, Glatt H. (2009)
Probenecid, an inhibitor of transmembrane organic anion transporters, alters tissue distribution of DNA adducts in 1-hydroxymethylpyrene-treated rats.
Toxicology, 262 (1): 80-5. [PMID:19481134]
12. Nakamichi N, Ishimoto T, Yamauchi Y, Masuo Y, Kato Y. (2016)
Screening to Identify Multidrug Resistance-Associated Protein Inhibitors with Neuroblastoma-Selective Cytotoxicity.
Biol Pharm Bull, 39 (10): 1638-1645. [PMID:27725440]
13. Tan PK, Ostertag TM, Miner JN. (2016)
Mechanism of high affinity inhibition of the human urate transporter URAT1.
Sci Rep, 6: 34995. [PMID:27713539]
14. Youngblood GL, Sweet DH. (2004)
Identification and functional assessment of the novel murine organic anion transporter Oat5 (Slc22a19) expressed in kidney.
Am J Physiol Renal Physiol, 287 (2): F236-44. [PMID:15068970]