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Details

Stereochemistry ACHIRAL
Molecular Formula C13H18NO4S.Na
Molecular Weight 307.341
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROBENECID SODIUM

SMILES

[Na+].CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C([O-])=O

InChI

InChIKey=QCCCFHDTBTUDEA-UHFFFAOYSA-M
InChI=1S/C13H19NO4S.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Description

Probenecid is the prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy. Probenecid is used for treatment of the hyperuricemia associated with gout and gouty arthritis. Probenecid is a uricosuric and renal tubular blocking agent. It inhibits the tubular reabsorption of urate, thus increasing the urinary excretion of uric acid and decreasing serum urate levels. Effective uricosuria reduces the miscible urate pool, retards urate deposition, and promotes resorption of urate deposits. Probenecid inhibits the tubular secretion of penicillin and usually increases penicillin plasma levels by any route the antibiotic is given. A 2-fold to 4-fold elevation has been demonstrated for various penicillins. Probenecid decreases both hepatic and renal excretion of sulfobromophthalein (BSP). The tubular reabsorption of phosphorus is inhibited in hypoparathyroid but not in euparathyroid individuals. Probenecid does not influence plasma concentrations of salicylates, nor the excretion of streptomycin, chloramphenicol, chlortetracycline, oxytetracycline, or neomycin.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
12.1 µM [Ki]
5.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PROBENECID
Palliative
PROBENECID

Cmax

ValueDoseCo-administeredAnalytePopulation
148.6 μg/mL
2000 mg single, oral
PROBENECID plasma
Homo sapiens
35.3 μg/mL
500 mg single, oral
PROBENECID plasma
Homo sapiens
69.6 μg/mL
1000 mg single, oral
PROBENECID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2109 μg × h/mL
2000 mg single, oral
PROBENECID plasma
Homo sapiens
292 μg × h/mL
500 mg single, oral
PROBENECID plasma
Homo sapiens
772 μg × h/mL
1000 mg single, oral
PROBENECID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.5 h
2000 mg single, oral
PROBENECID plasma
Homo sapiens
4.2 h
500 mg single, oral
PROBENECID plasma
Homo sapiens
4.9 h
1000 mg single, oral
PROBENECID plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Gout: The recommended adult dosage is 250 mg (1/2 tablet) twice a day for one week, followed by 500 mg (1 tablet) twice a day thereafter.
Route of Administration: Oral
In Vitro Use Guide
Probenecid, at concentrations that had no effect on parasite viability alone (50 uM), was shown to increase the sensitivity of a highly resistant parasite isolate to the antifolates pyrimethamine, sulfadoxine, chlorcycloguanil, and dapsone by seven-, five-, three-, and threefold, respectively. Probenecid decreased the level of uptake of radiolabeled folic acid, suggesting a transport-based mechanism linked to folate salvage.