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Details

Stereochemistry ACHIRAL
Molecular Formula C13H19NO4S
Molecular Weight 285.359
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROBENECID

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)

HIDE SMILES / InChI

Molecular Formula C13H19NO4S
Molecular Weight 285.359
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

PubMed

TitleDatePubMed
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
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
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
Membrane Based Measurement Technology for in situ Monitoring of Gases in Soil.
2009
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
Prognostic significance of p53-expression in colorectal carcinoma as measured by a luminometric immunoassay.
2010 Oct 8
Interactions of urate transporter URAT1 in human kidney with uricosuric drugs.
2011 Feb
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
Patents

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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:43:19 UTC 2019
Edited
by admin
on Tue Oct 22 00:43:19 UTC 2019
Record UNII
PO572Z7917
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROBENECID
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
PROBENECID [USP-RS]
Common Name English
PROBAMPACIN COMPONENT PROBENECID
Common Name English
PROBENECID [WHO-DD]
Common Name English
PROBENECID [ORANGE BOOK]
Common Name English
PROBENECID [MART.]
Common Name English
PROBENECID [EP]
Common Name English
PROBENECID [USP]
Common Name English
PROBENATE
Common Name English
BENZOIC ACID, 4-((DIPROPYLAMINO)SULFONYL)-
Common Name English
PROBENECID [JAN]
Common Name English
PROBENECID COMPONENT OF COLBENEMID
Common Name English
PROBENECID [INN]
Common Name English
PROBENECID COMPONENT OF PROBAMPACIN
Common Name English
HC 5006
Code English
PROBENECID COMPONENT OF COL-PROBENECID
Common Name English
P-(DIPROPYLSULFAMOYL)BENZOIC ACID
Common Name English
PROBENECID [MI]
Common Name English
BENEMID
Brand Name English
PROBENECID [HSDB]
Common Name English
PROBENECID COMPONENT OF PROBEN-C
Common Name English
NSC-18786
Code English
PROBENECID [WHO-IP]
Common Name English
PROBENECIDUM [WHO-IP LATIN]
Common Name English
PROBENECID [VANDF]
Common Name English
PROBEN-C COMPONENT PROBENECID
Common Name English
COL-PROBENECID COMPONENT PROBENECID
Common Name English
COLBENEMID COMPONENT PROBENECID
Common Name English
PROBALAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C921
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
LIVERTOX 799
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
WHO-ATC M04AB01
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
WHO-VATC QM04AB01
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
Code System Code Type Description
IUPHAR
4357
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
HSDB
57-66-9
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
MERCK INDEX
M9142
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY Merck Index
EVMPD
SUB10053MIG
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL897
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
EPA CompTox
57-66-9
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
WIKIPEDIA
Probenecid
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
CAS
57-66-9
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
MESH
D011339
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
RXCUI
8698
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
PROBENECID
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
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.
LactMed
57-66-9
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
INN
563
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
DRUG BANK
DB01032
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
NCI_THESAURUS
C772
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-344-3
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
PUBCHEM
4911
Created by admin on Tue Oct 22 00:43:19 UTC 2019 , Edited by admin on Tue Oct 22 00:43:19 UTC 2019
PRIMARY
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