Probenecid

from Wikipedia, the free encyclopedia
Structural formula
Structure of probenecid
General
Non-proprietary name Probenecid
other names
  • 4- (Dipropylsulfamoyl) benzoic acid ( IUPAC )
  • Probenecidum ( Latin )
Molecular formula
  • C 13 H 19 NO 4 S (probenecid)
  • C 13 H 19 NNaO 4 S (probenecid sodium salt )
Brief description

slightly bitter-tasting crystals with a pleasant aftertaste

External identifiers / databases
CAS number
  • 57-66-9 (probenecid)
  • 23795-03-1 (probenecid sodium salt)
EC number 200-344-3
ECHA InfoCard 100,000,313
PubChem 4911
DrugBank DB01032
Wikidata Q900898
Drug information
ATC code

M04 AB01

Drug class

Urikosurika

properties
Molar mass 285.36 g · mol -1 (probenecid)
Physical state

firmly

Melting point

194–196 ° C (probenecid)

pK s value

5.8

solubility

practically insoluble in water (probenecid)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data
  • 1604 mg kg −1 ( LD 50 ,  rat ,  oral , probenecid sodium salt)
  • 394 mg kg −1 ( LD 50 ,  rat ,  ip , probenecid sodium salt)
  • 611 mg kg −1 ( LD 50 ,  rat ,  sc , probenecid sodium salt)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Probenecid is a drug used to treat hyperuricemia or gout . It belongs to the so-called uricosuric drugs . MSD Sharp & Dohme received a patent for probenecid . It is available in Switzerland under the trade name Santuril ; available in Germany as a generic .

Mechanism of action

Probenecid is a strong inhibitor of OA is - (organic anions) - secretion of the proximal tubular cells of the kidney. It inhibits the OAT1 (organic anion transporter type 1) on the basolateral side of the cell. The OAT1 takes OA - (.. P-aminohippurate, phenol red, urate, penicillin, barbiturates u a) from the blood into the tubule cells, in exchange with dicarboxylates like succinate and 2-oxoglutarate.

The main mechanism of action of probenecid is to increase the renal excretion of uric acid . It inhibits the tubular reabsorption of uric acid in the kidneys and thereby increases its excretion in the urine . Probenecid has no influence on the formation of uric acid.

Pharmacokinetics

In the online edition of the journal Nature of November 1, 2005, the substance was ascribed the property of significantly reducing the excretion of oseltamivir ( Tamiflu ® , an agent against influenza A diseases ), so that the same antiviral effect is achieved at half the dose could be. In the event of a flu pandemic, the possibly inadequate supply of this drug can be improved accordingly. However, since the effect also affects many other drugs, its use should be problematic , especially in risk groups with underlying diseases such as diabetes or conditions after a heart attack .

doping

Probenecid is on the WADA anti-doping list as a masking agent .

Individual evidence

  1. ↑ a b c Entry on probenecid. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  2. ↑ a b c d e The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1333, ISBN 978-0-911910-00-1 .
  3. ↑ a b data sheet probenecid from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
  4. ↑ Butler D: Wartime tactic doubles power of scarce bird-flu drug . In: Nature . 438 , No. 7064, November 2005, p. 6. doi : 10.1038 / 438006a . PMID 16267514 .
  5. ↑ List of prohibited substances and methods (DOPING LIST) ( Memento of April 23, 2016 in the Internet Archive ), valid from January 1, 2007.