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Probenecid

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Probenecid chemical structure
Probenecid

4-(dipropylsulfamoyl)benzoic acid
IUPAC name
CAS number
57-66-9
ATC code

M04AB01

PubChem
4911
DrugBank
APRD00167
Chemical formula {{{chemical_formula}}}
Molecular weight 285.36 g/mol
Bioavailability
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 oral

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

Probenecid competitively inhibits the renal excretion of some drugs, thereby increasing their plasma concentration and prolonging their effects.

It was developed as an alternative to caronamide.[1]

UsesEdit

In one study, probenecid was shown to more than double blood concentrations of oseltamivir (trade name Tamiflu), an antiviral drug used to combat influenza.[2] This is significant because nations are currently stockpiling oseltamivir in anticipation of an influenza pandemic, and there could be supply shortages.[How to reference and link to summary or text] During World War II, probenecid was used to extend limited supplies of penicillin,[3] and is still currently used to increase antibiotic concentrations in serious infections.

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

MechanismEdit

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

Probenecid's exact mechanism is explained as follows. The kidney's organic anion transporter (OAT) reclaims uric acid from the urine and returns it to the plasma. Probenecid interferes with these systems.[5] 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 alsoEdit

ReferencesEdit

  1. MASON RM (June 1954). Studies on the effect of probenecid (benemid) in gout. Ann. Rheum. Dis. 13 (2): 120–30.
  2. 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.
  3. Butler D (2005). Wartime tactic doubles power of scarce bird-flu drug. Nature 438 (7064): 6.
  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.
  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.

Template:Antigout preparations

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