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Pirprofen

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Chemical compound

Pharmaceutical compound
Pirprofen
Clinical data
ATC code
Identifiers
IUPAC name
  • 2-propanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.172 Edit this at Wikidata
Chemical and physical data
FormulaC13H14ClNO2
Molar mass251.71 g·mol
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)
  • Key:PIDSZXPFGCURGN-UHFFFAOYSA-N
  (what is this?)  (verify)

Pirprofen was a nonsteroidal anti-inflammatory drug (NSAID) 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. Ciba-Geigy voluntarily withdrew the drug from the market worldwide in 1990.

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. S2CID 195692709.
  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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use.
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators


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