Probenecid

Systematic (IUPAC) name
4-(dipropylsulfamoyl)benzoic acid
Identifiers
CAS number	57-66-9
ATC code	M04AB01
PubChem	4911
DrugBank	APRD00167
Chemical data
Formula	C13H19NO4S
Mol. mass	285.36 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	75-95%
Metabolism	?
Half life	2-6 hours (dose: 0.5-1 g) 4-12 hours (dose: >2 g)
Excretion	renal (77-88%)
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	oral
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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]

Contents 1 Uses 2 Mechanism 3 See also 4 References

[edit] Uses

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.^{[citation needed]} 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]

[edit] Mechanism

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.

[edit] See also

• Probenecid and colchicine

[edit] References

v • d • e Antigout preparations (M04) Uricosurics primary: Probenecid · Sulfinpyrazone · Benzbromarone · Isobromindione secondary: Amlodipine · Atorvastatin · Fenofibrate · Guaifenesin · Losartan Xanthine oxidase inhibitors purine analogues: Allopurinol# · Oxypurinol · Tisopurine other: Febuxostat · Inositols (Phytic acid, Myo-inositol) Mitotic inhibitors Colchicine Other Cinchophen · NSAIDs except aspirin · Sevelamer · Urate oxidase (Rasburicase, Pegloticase†) #WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III