Probenecid

Probenecid
Systematic (IUPAC) name
4-(dipropylsulfamoyl)benzoic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682395
Pregnancy cat.  ?
Legal status  ?
Routes oral
Pharmacokinetic data
Protein binding 75-95%
Half-life 2-6 hours (dose: 0.5-1 g)
Excretion renal (77-88%)
Identifiers
CAS number 57-66-9 YesY
ATC code M04AB01
PubChem CID 4911
DrugBank APRD00167
ChemSpider 4742 YesY
UNII PO572Z7917 YesY
KEGG D00475 YesY
ChEMBL CHEMBL897 YesY
Chemical data
Formula C13H19NO4S 
Mol. mass 285.36 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Probenecid (Benuryl, Benemid, Probalan) is a uricosuric drug that increases uric acid excretion in the urine. It is primarily used in treating gout and hyperuricemia.

Probenecid was developed as an alternative to caronamide.[1] Their primary goal was to competitively inhibit renal excretion of some drugs, thereby increasing their plasma concentration and prolonging their effects.

Contents

Uses

During World War II, probenecid was used to extend limited supplies of penicillin,[2] and is still currently used to increase antibiotic concentrations in serious infections. In one study, probenecid was shown to more than double blood concentrations of oseltamivir (trade name Tamiflu), an antiviral drug used to combat influenza, suggesting that this property applies to antivirals as well.[3]

It has also found use as a masking agent.[4]

Drug Interactions

Some of the important clinical interactions of Probenecid include those with Captopril, Indomethacin, Ketoprofen, Ketorolac, Naproxen, Cephalosporins, Quinolones, Penicillins, Methotrexate, Zidovudine, Gancyclovir, Aciclovir. In all these interactions the excretion of these drugs is reduced due to Probenecid.

Pharmacology

In the kidneys probenecid is filtered at the glomerulus, secreted in the proximal tubule and reabsorbed in the distal tubule.

Probenecid works by interfering with the kidney's organic anion transporter (OAT), which reclaims uric acid from the urine and returns it to the plasma.[5] If probenecid (an organic acid) is present, the OAT binds preferentially to it (instead of to uric acid), preventing re-absorption of the uric acid. Hence, the urine retains more uric acid, lowering uric acid concentration in the plasma. (This is a good example of a medical usage for competition between substrates transported across cell membranes). Probenecid also inhibits pannexin channels.[6]

See also

References

  1. ^ MASON RM (June 1954). "Studies on the Effect of Probenecid ('Benemid') in Gout". Ann. Rheum. Dis. 13 (2): 120–30. doi:10.1136/ard.13.2.120. PMC 1030399. PMID 13171805. http://ard.bmj.com/cgi/pmidlookup?view=long&pmid=13171805. 
  2. ^ Butler D (2005). "Wartime tactic doubles power of scarce bird-flu drug". Nature 438 (7064): 6. doi:10.1038/438006a. PMID 16267514. http://www.nature.com/nature/journal/v438/n7064/full/438006a.html. 
  3. ^ Hill G, Cihlar T, Oo C et al. (2002). "The anti-influenza drug oseltamivir exhibits low potential to induce pharmacokinetic drug interactions via renal secretion-correlation of in vivo and in vitro studies". Drug Metab. Dispos. 30 (1): 13–9. doi:10.1124/dmd.30.1.13. PMID 11744606. http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11744606. 
  4. ^ Morra V, Davit P, Capra P, Vincenti M, Di Stilo A, Botrè F (December 2006). "Fast gas chromatographic/mass spectrometric determination of diuretics and masking agents in human urine: Development and validation of a productive screening protocol for antidoping analysis". J Chromatogr A 1135 (2): 219–29. doi:10.1016/j.chroma.2006.09.034. PMID 17027009. http://linkinghub.elsevier.com/retrieve/pii/S0021-9673(06)01791-2. 
  5. ^ Hsyu PH, Gisclon LG, Hui AC, Giacomini KM (January 1988). "Interactions of organic anions with the organic cation transporter in renal BBMV". Am. J. Physiol. 254 (1 Pt 2): F56–61. PMID 2962517. http://ajprenal.physiology.org/cgi/pmidlookup?view=reprint&pmid=2962517. 
  6. ^ Silverman W, Locovei S, Dahl G (September 2008). "Probenecid, a gout remedy, inhibits pannexin 1 channels". Am J Physiol Cell Physiol 295 (3): C761-7. PMID 18596212. http://ajpcell.physiology.org/content/295/3/C761.abstract. 

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Look at other dictionaries:

  • Probenecid — Saltar a navegación, búsqueda Probenecid A …   Wikipedia Español

  • probenecid — Uricosúrico y coadyuvante de los antibióticos. Se prescribe para el tratamiento de la gota y como coadyuvante para prolongar la actividad de la penicilina o de las cefalosporinas en algunas infecciones, como la gonorrea …   Diccionario médico

  • probenecid — [prō ben′ə sid] n. a white, crystalline drug, C13H19NO4S, that influences the ability of the kidney to separate various compounds from the blood, used to increase the urinary excretion of uric acid in cases of gout and to decrease the urinary… …   English World dictionary

  • Probenecid — Strukturformel Allgemeines Freiname Probenecid Andere Namen …   Deutsch Wikipedia

  • probenecid — /proh ben euh sid/, n. Pharm. a white, crystalline, water insoluble powder, C13H19NO4S, used chiefly in the treatment of gout. [1945 50; PRO(PYL) + BEN(ZEN)E + (A)CID] * * * ▪ drug       drug used in the treatment of chronic gout, a disorder that …   Universalium

  • probenecid — noun Etymology: irregular from propyl + benzoic acid Date: 1950 a drug C13H19NO4S that acts on renal tubular function and is used to increase the concentration of some drugs (as penicillin) in the blood by inhibiting their excretion and to… …   New Collegiate Dictionary

  • probenecid — noun A particular pharmaceutical drug used to treat hyperuricemia …   Wiktionary

  • probenecid — A competitive inhibitor of the secretion of penicillin or p aminohippurate by kidney tubules; a uricosuric agent used in chronic gouty arthritis. * * * pro·ben·e·cid prō ben ə səd n a drug C13H19 …   Medical dictionary

  • probenecid — n. drug used to treat arthritis …   English contemporary dictionary

  • probenecid — pro·ben·e·cid …   English syllables

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