Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H19NO4S |
| Molecular Weight | 285.359 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O
InChI
InChIKey=DBABZHXKTCFAPX-UHFFFAOYSA-N
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)
| Molecular Formula | C13H19NO4S |
| Molecular Weight | 285.359 |
| Charge | 0 |
| 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 Date4.17743995E11 |
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| 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 Date4.17743995E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
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 |
|---|---|---|
| Nephrotic syndrome caused by probenecid. | 1967 Jan 2 |
|
| Probenecid, nephrotic syndrome, and renal failure. | 1968 May |
|
| Penicillin-induced haemolytic anaemia. | 1968 Sep 7 |
|
| Probenecid and renal failure. | 1968 Sep 7 |
|
| Haematuria during methicillin therapy. | 1971 Jul |
|
| Probenecid-induced nephrotic syndrome. | 1972 Sep |
|
| Acute Heinz-body anaemia in burned patients. | 1973 Sep 1 |
|
| Letter: Drug-induced red cell aplasia. | 1974 Oct 19 |
|
| Skin sensitizing properties of arylalcanoic acids and their analogues. | 1979 Sep |
|
| Treatment of gonorrhea: comparison of cefotaxime and penicillin. | 1981 May |
|
| Effect of probenecid on the natriuresis and renin release induced by bumetanide in man. | 1981 Nov-Dec |
|
| One gram of cefoxitin cures uncomplicated gonococcal urethritis caused by penicillinase-producing Neisseria gonorrhoeae (PPNG). | 1983 Jul-Sep |
|
| Enhancement of cisplatin nephrotoxicity by probenecid. | 1984 Feb |
|
| Immune hemolytic anemia associated with probenecid. | 1985 Sep |
|
| Probenecid induced immune hemolytic anemia. | 1986 Feb |
|
| Mechanism of S-(1,2-dichlorovinyl)glutathione-induced nephrotoxicity. | 1986 Jan 15 |
|
| The mechanisms of target cell injury by nephrotoxins. | 1986 Jun-Jul |
|
| In vivo nephrotoxic action of an isomeric mixture of S-(1-phenyl-2-hydroxyethyl)glutathione and S-(2-phenyl-2-hydroxyethyl)glutathione in Fischer-344 rats. | 1991 Mar 25 |
|
| Beta-trace protein (prostaglandin D synthase)--a stable and reliable protein in perilymph. | 2005 Jun 23 |
|
| Membrane transporter proteins: a challenge for CNS drug development. | 2006 |
|
| A concise history of gout and hyperuricemia and their treatment. | 2006 |
|
| Transport of estrone sulfate by the novel organic anion transporter Oat6 (Slc22a20). | 2006 Aug |
|
| Inhibitory effects of angiotensin II receptor antagonists and leukotriene receptor antagonists on the transport of human organic anion transporter 4. | 2006 Nov |
|
| Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. | 2006 Oct |
|
| One center's experience: the serology and drugs associated with drug-induced immune hemolytic anemia--a new paradigm. | 2007 Apr |
|
| Probenecid-induced membranous nephropathy. | 2007 Aug |
|
| Multidrug resistance protein 1 (MRP1) in rabbit conjunctival epithelial cells: its effect on drug efflux and its regulation by adenoviral infection. | 2007 Aug |
|
| In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
| Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways. | 2007 Oct |
|
| Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients. | 2007 Sep |
|
| Transient receptor potential V2 expressed in sensory neurons is activated by probenecid. | 2007 Sep 25 |
|
| Neuroprotective effect of long-term NDI1 gene expression in a chronic mouse model of Parkinson disorder. | 2009 Aug |
|
| Pharmacological characterization of pannexin-1 currents expressed in mammalian cells. | 2009 Feb |
|
| Efficacy and tolerability of urate-lowering drugs in gout: a randomised controlled trial of benzbromarone versus probenecid after failure of allopurinol. | 2009 Jan |
|
| 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 Jan 30 |
|
| Detection of HER-2/neu, c-myc amplification and p53 inactivation by FISH in Egyptian patients with breast cancer. | 2009 May 6 |
|
| Pannexin 1 contributes to ATP release in airway epithelia. | 2009 Nov |
|
| Molecular evidence for an involvement of organic anion transporters (OATs) in aristolochic acid nephropathy. | 2009 Oct 1 |
|
| 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 Jan |
|
| Multidrug resistance proteins restrain the intestinal absorption of trans-resveratrol in rats. | 2010 Mar |
|
| Biliary efflux transporters involved in the clearance of rosuvastatin in sandwich culture of primary rat hepatocytes. | 2010 Mar |
|
| 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 Oct |
|
| Interactions of human organic anion transporter 1 (hOAT1) with substances associated with forensic toxicology. | 2011 Jul |
|
| Uricosuric and nephroprotective properties of Ramulus Mori ethanol extract in hyperuricemic mice. | 2012 Oct 11 |
|
| Targeting organic anion transporter 3 with probenecid as a novel anti-influenza a virus strategy. | 2013 Jan |
|
| Interactions with selected drug renal transporters and transporter-mediated cytotoxicity in antiviral agents from the group of acyclic nucleoside phosphonates. | 2013 Sep 15 |
|
| 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 Jan |
|
| 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 Jun 25 |
|
| Neuroprotective effect of the chemical chaperone, trehalose in a chronic MPTP-induced Parkinson's disease mouse model. | 2014 Sep |
|
| Novel para-phenyl substituted diindolylmethanes protect against MPTP neurotoxicity and suppress glial activation in a mouse model of Parkinson's disease. | 2015 Feb |
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
by
admin
on
Edited
Fri Dec 16 16:52:37 UTC 2022
by
admin
on
Fri Dec 16 16:52:37 UTC 2022
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| Record UNII |
PO572Z7917
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C921
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LIVERTOX |
NBK548599
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WHO-ATC |
M04AB01
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WHO-VATC |
QM04AB01
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PO572Z7917
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4357
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Probenecid
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3387
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M9142
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SUB10053MIG
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CHEMBL897
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DTXSID9021188
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Probenecid
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57-66-9
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1563003
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2268
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D011339
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18786
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8698
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PROBENECID
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 25 parts of ethanol (~750 g/l) TS and in 12 parts of acetone R; soluble in dilutesolutions of alkali hydroxides. Category: Antigout drug. Storage: Probenecid should be kept in a well-closed container. Definition: Probenecid contains not less than 98.0% and not more than 101.0% of C13H19NO4S, calculated with reference to thedried substance. | ||
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PO572Z7917
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8426
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563
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DB01032
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C772
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200-344-3
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4911
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Primary target.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
