Ligand id: 4357

Name: probenecid

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View more information in the IUPHAR Pharmacology Education Project: probenecid

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 83.06
Molecular weight 285.1
XLogP 2.31
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

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. U.S.A., 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]