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
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
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. 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]