Pirprofen

Pirprofen was a nonsteroidal anti-inflammatory drug (NSAID)[1] that was brought to market by Ciba-Geigy in 1982 as a treatment for arthritis and pain. Its label was restricted after adverse events arose, including some cases of fatal liver toxicity.[2] Ciba-Geigy voluntarily withdrew the drug from the market worldwide in 1990.[3]: 223 

Pirprofen
Clinical data
ATC code
Identifiers
IUPAC name
  • 2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.172
Chemical and physical data
FormulaC13H14ClNO2
Molar mass251.71 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)C(c1cc(Cl)c(cc1)N2C/C=C\C2)C
InChI
  • InChI=1S/C13H14ClNO2/c1-9(13(16)17)10-4-5-12(11(14)8-10)15-6-2-3-7-15/h2-5,8-9H,6-7H2,1H3,(H,16,17) Y
  • Key:PIDSZXPFGCURGN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

References
  1. Todd PA, Beresford R (December 1986). "Pirprofen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy". Drugs. 32 (6): 509–37. doi:10.2165/00003495-198632060-00003. PMID 3539573.
  2. Depla AC, Vermeersch PH, van Gorp LH, Nadorp JH (August 1990). "Fatal acute liver failure associated with pirprofen. Report of a case and a review of the literature". The Netherlands Journal of Medicine. 37 (1–2): 32–6. PMID 2215831.
  3. WHO. Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals. United Nations - New York, 2005


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