Probenecid 3210446 215488803 2008-05-28T12:41:29Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{drugbox | IUPAC_name = 4-(dipropylsulfamoyl)benzoic acid | image = Probenecid.svg | width = 142 | CAS_number = 57-66-9 | ATC_prefix = M04 | ATC_suffix = AB01 | ATC_supplemental = | PubChem = 4911 | DrugBank = APRD00167 | C=13 | H=19 | N=1 | O=4 | S=1 | molecular_weight = 285.36 g/mol | bioavailability = | protein_bound = 75-95% | metabolism = | elimination_half-life = 2-6 hours (dose: 0.5-1 g) 4-12 hours (dose: >2 g) | excretion = renal (77-88%) | pregnancy_category = | legal_status = | routes_of_administration = }} '''Probenecid''' is a [[uricosuric]] drug, primarily used in treating [[gout]] or [[hyperuricemia]], that increases uric acid removal in the urine. One of its trade names is 'Benuryl.' Probenecid also decreases the renal excretion of some drugs. In one study, probenecid was shown to more than double blood concentrations of [[oseltamivir]] (trade name Tamiflu), an antiviral drug used to combat influenza.<ref name="pmid11744606">{{cite journal | author = Hill G, Cihlar T, Oo C, ''et al'' | title = The anti-influenza drug oseltamivir exhibits low potential to induce pharmacokinetic drug interactions via renal secretion-correlation of in vivo and in vitro studies | journal = Drug Metab. Dispos. | volume = 30 | issue = 1 | pages = 13–9 | year = 2002 | pmid = 11744606 | doi = | url = http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11744606 }}</ref> This is significant because nations are currently stockpiling oseltamivir in anticipation of an [[influenza pandemic]], and there could be supply shortages.{{Fact|date=December 2007}} During World War II, probenecid was used to extend limited supplies of [[penicillin]],<ref>{{cite journal |author=Butler D |title=Wartime tactic doubles power of scarce bird-flu drug |journal=Nature |volume=438 |issue=7064 |pages=6 |year=2005 |pmid=16267514 |url=http://www.nature.com/nature/journal/v438/n7064/full/438006a.html |doi=10.1038/438006a}}</ref> and is still currently used to increase antibiotic concentrations in serious infections. It has also found use as a masking agent by athletes attempting to get away with using performance enhancing drugs.{{Fact|date=March 2008}} In the kidneys it is filtered at the glomerulus, secreted in the proximal tubule and reabsorbed in the distal tubule. Probenecid's exact mechanism is explained as follows. Gout is caused by elevated levels of uric acid in the plasma which can lead to the formation of uric acid crystals in joints, causing pain. The kidney's organic anion transporter (OAT) reclaims uric acid from the urine and returns it to the plasma. If probenecid (an organic acid) is administered to a patient, the OAT binds to probenecid instead of to uric acid, preventing the reabsorption of uric acid. As a result, more uric acid leaves the body in the urine, lowering the uric acid concentration in the plasma. This is an example of the way in which competition between substrates transported across cell membranes has been put to use in medicine. ==See also== * [[Gout]] ==References== <references/> * [http://mado.alp.mcgill.ca:8100/meded/drugdb/probenecid/probenecid_db.htm Probenecid pharmacology from McGill University] {{Antigout preparations}} [[Category:Antigout agents]] [[de:Probenecid]] [[fr:Probénécide]] [[pl:Probenecid]] [[pt:Probenecida]]