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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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
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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)
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. 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]
8. 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]
9. 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]
10. 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]
11. 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]
12. Tan PK, Ostertag TM, Miner JN. (2016)
Mechanism of high affinity inhibition of the human urate transporter URAT1.
Sci Rep, 6: 34995. [PMID:27713539]
13. 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]