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
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
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C13H18NO4S |
| Molecular Weight | 284.351 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Curator's Comment: After the incidental finding that caronamide, had a uricosuric action (Wolfson and others, 1948), Boger and others (1950) showed that p-(di-n-propylsulphamyl)-benzoic acid (probenecid, 'Benemid') had a similar and more potent effect, and appeared to be less toxic (Boger and Crosson, 1950).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1641347 |
12.1 µM [Ki] | ||
Target ID: CHEMBL1641348 |
5.6 µM [IC50] | ||
Target ID: CHEMBL2073677 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | PROBENECID Approved UseFor treatment of the hyperuricemia associated with gout and gouty arthritis. As an adjuvant to therapy with penicillin or with ampicillin, methicillin, oxacillin, cloxacillin, or nafcillin, for elevation and prolongation of plasma levels by whatever route the antibiotic is given. Launch Date1983 |
|||
| Palliative | PROBENECID Approved UseFor treatment of the hyperuricemia associated with gout and gouty arthritis. As an adjuvant to therapy with penicillin or with ampicillin, methicillin, oxacillin, cloxacillin, or nafcillin, for elevation and prolongation of plasma levels by whatever route the antibiotic is given. Launch Date1983 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
69.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
148.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
292 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
772 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2109 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7175716/ |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROBENECID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| weak | ||||
| yes [IC50 100 uM] | yes (co-administration study) Comment: MRP4-expressing V79 vesicles (cholyltaurine); Coadministration of Probenecid (1000 mg QD oral) increased Cefmetazole (5 mg/kg QD IV-infusion (1-hr)) AUC by 1.6-fold. |
|||
| yes [IC50 3.1 uM] | yes (co-administration study) Comment: CHO-OAT3 (cimetidine); Coadministration of Probenecid (1000 mg QD oral) increased Dicloxacillin (500 mg SD oral) AUC by 1.9-fold and Cmax by 1.8-fold. |
|||
| yes [IC50 3.9 uM] | yes (co-administration study) Comment: CHO-OAT1 (cidofovir); Coadministration of Probenecid (1000 mg QD oral) increased Dicloxacillin (500 mg SD oral) AUC by 1.9-fold and Cmax by 1.8-fold. |
|||
| yes [IC50 34 uM] | yes (co-administration study) Comment: MRP5-expressing HEK293 vesicles (carboxydichlorofluorescein); Coadministration of Probenecid (1000 mg QD oral) increased Cefmetazole (2000 mg QD IV-infusion (5 min)) AUC by 1.6-fold. |
|||
| yes [Ki 54.9 uM] | ||||
| yes [Ki 766 uM] | yes (co-administration study) Comment: S2-OAT2 (prostaglandin F2alpha); Coadministration of Probenecid (1000 mg QD oral) increased Dicloxacillin (500 mg SD oral) AUC by 1.9-fold and Cmax by 1.8-fold. |
|||
| yes | yes (co-administration study) Comment: Coadministration of Probenecid (1000 mg qid on Day 1, 500 mg qid on Days 2-3, and 500 mg QD on Day 4) increased Naproxen (500 mg QD on Day 4) AUCinf by over 2-fold. |
|||
| yes | yes (co-administration study) Comment: Coadministration of Probenecid (500 mg BID X 10 days) decreased Carbamazepine (200 mg QD on Day 6) AUCinf by 18% and increased Cmax by 3% while increased Carbamazepine 10,11-epoxide AUCinf by 35% and Cmax by 47%. |
|||
| yes | yes (co-administration study) Comment: Coadministration of Probenecid (1000 mg qid on Day 1, 500 mg qid on Days 2-3, and 500 mg QD on Day 4) increased Naproxen (500 mg QD on Day 4) AUCinf by over 2-fold. |
|||
| yes | yes (co-administration study) Comment: Coadministration of Probenecid (500 mg BID X 10 days) decreased Carbamazepine (200 mg QD on Day 6) AUCinf by 18% and increased Cmax by 3% while increased Carbamazepine 10,11-epoxide AUCinf by 35% and Cmax by 47%. |
|||
| yes | yes (co-administration study) Comment: Coadministration of Probenecid (500 mg q8h X 3 days) increased Zidovudine (q8h x 3 day) AUC by 80%. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Novel para-phenyl substituted diindolylmethanes protect against MPTP neurotoxicity and suppress glial activation in a mouse model of Parkinson's disease. | 2015-02 |
|
| Neuroprotective effect of the chemical chaperone, trehalose in a chronic MPTP-induced Parkinson's disease mouse model. | 2014-09 |
|
| Gene expression regulation of Bcl2, Bax and cytochrome-C by geraniol on chronic MPTP/probenecid induced C57BL/6 mice model of Parkinson's disease. | 2014-06-25 |
|
| A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. | 2014-01 |
|
| Interactions with selected drug renal transporters and transporter-mediated cytotoxicity in antiviral agents from the group of acyclic nucleoside phosphonates. | 2013-09-15 |
|
| Targeting organic anion transporter 3 with probenecid as a novel anti-influenza a virus strategy. | 2013-01 |
|
| Uricosuric and nephroprotective properties of Ramulus Mori ethanol extract in hyperuricemic mice. | 2012-10-11 |
|
| Interactions of human organic anion transporter 1 (hOAT1) with substances associated with forensic toxicology. | 2011-07 |
|
| Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. | 2011-02 |
|
| Prognostic significance of p53-expression in colorectal carcinoma as measured by a luminometric immunoassay. | 2010-10-08 |
|
| Characterization of cellular uptake of perfluorooctanoate via organic anion-transporting polypeptide 1A2, organic anion transporter 4, and urate transporter 1 for their potential roles in mediating human renal reabsorption of perfluorocarboxylates. | 2010-10 |
|
| Multidrug resistance proteins restrain the intestinal absorption of trans-resveratrol in rats. | 2010-03 |
|
| Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes. | 2010-03 |
|
| On call. I've had gout for many years. I used to take Zyloprim without any problems, but I just had a severe allergic reaction, so my doctor switched me to Benemid. I'm doing okay, but the drug sometimes upsets my stomach. Do you have any suggestions? | 2010-01 |
|
| Pannexin 1 contributes to ATP release in airway epithelia. | 2009-11 |
|
| Molecular evidence for an involvement of organic anion transporters (OATs) in aristolochic acid nephropathy. | 2009-10-01 |
|
| Neuroprotective effect of long-term NDI1 gene expression in a chronic mouse model of Parkinson disorder. | 2009-08 |
|
| Detection of HER-2/neu, c-myc amplification and p53 inactivation by FISH in Egyptian patients with breast cancer. | 2009-05-06 |
|
| Pharmacological characterization of pannexin-1 currents expressed in mammalian cells. | 2009-02 |
|
| Effects of endurance exercise on ventral tegmental area neurons in the chronic 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and probenecid-treated mice. | 2009-01-30 |
|
| Efficacy and tolerability of urate-lowering drugs in gout: a randomised controlled trial of benzbromarone versus probenecid after failure of allopurinol. | 2009-01 |
|
| Membrane Based Measurement Technology for in situ Monitoring of Gases in Soil. | 2009 |
|
| Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways. | 2007-10 |
|
| Transient receptor potential V2 expressed in sensory neurons is activated by probenecid. | 2007-09-25 |
|
| Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients. | 2007-09 |
|
| Probenecid-induced membranous nephropathy. | 2007-08 |
|
| Multidrug resistance protein 1 (MRP1) in rabbit conjunctival epithelial cells: its effect on drug efflux and its regulation by adenoviral infection. | 2007-08 |
|
| One center's experience: the serology and drugs associated with drug-induced immune hemolytic anemia--a new paradigm. | 2007-04 |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007-01 |
|
| Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4. | 2006-11 |
|
| Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. | 2006-10 |
|
| Membrane transporter proteins: a challenge for CNS drug development. | 2006 |
|
| Beta-trace protein (prostaglandin D synthase)--a stable and reliable protein in perilymph. | 2005-06-23 |
|
| The mechanisms of target cell injury by nephrotoxins. | 1986-06-01 |
|
| Probenecid induced immune hemolytic anemia. | 1986-02 |
|
| Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. | 1986-01-15 |
|
| Immune hemolytic anemia associated with probenecid. | 1985-09 |
|
| Enhancement of cisplatin nephrotoxicity by probenecid. | 1984-02 |
|
| One gram of cefoxitin cures uncomplicated gonococcal urethritis caused by penicillinase-producing Neisseria gonorrhoeae (PPNG). | 1983-07-01 |
|
| Effect of probenecid on the natriuresis and renin release induced by bumetanide in man. | 1981-11-01 |
|
| Treatment of gonorrhea: comparison of cefotaxime and penicillin. | 1981-05 |
|
| Skin sensitizing properties of arylalcanoic acids and their analogues. | 1979-09 |
|
| Letter: Drug-induced red cell aplasia. | 1974-10-19 |
|
| Acute Heinz-body anaemia in burned patients. | 1973-09-01 |
|
| Probenecid-induced nephrotic syndrome. | 1972-09 |
|
| Haematuria during methicillin therapy. | 1971-07 |
|
| Penicillin-induced haemolytic anaemia. | 1968-09-07 |
|
| Probenecid and renal failure. | 1968-09-07 |
|
| Probenecid, nephrotic syndrome, and renal failure. | 1968-05 |
|
| Nephrotic syndrome caused by probenecid. | 1967-01-02 |
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
FXB45Q4ZVK
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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DTXSID80178478
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m9142
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23795-03-1
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