Pirprofen

Chemical compound
  • M01AE08 (WHO)
Identifiers
  • 2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoic acid
CAS Number
  • 31793-07-4 ☒N
PubChem CID
  • 35935
ChemSpider
  • 33051 checkY
UNII
  • T7KN291890
KEGG
  • D05515 checkY
ChEMBL
  • ChEMBL188952 checkY
CompTox Dashboard (EPA)
  • DTXSID7023489 Edit this at Wikidata
ECHA InfoCard100.046.172 Edit this at WikidataChemical and physical dataFormulaC13H14ClNO2Molar mass251.71 g·mol−13D model (JSmol)
  • Interactive image
  • 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) checkY
  • Key:PIDSZXPFGCURGN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 

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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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
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Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidinessalicylatesacetic acid derivatives
and related substancesoxicamspropionic acid
derivatives (profens)n-arylanthranilic
acids (fenamates)COX-2 inhibitors
(coxibs)otherNSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; withdrawn drugs; veterinary use.
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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
  • Antagonists: AH-6809
  • ONO-8130
  • SC-19220
  • SC-51089
  • SC-51322
EP2Tooltip Prostaglandin EP2 receptor
  • Antagonists: AH-6809
  • PF-04418948
  • TG 4-155
EP3Tooltip Prostaglandin EP3 receptor
  • Antagonists: L-798106
EP4Tooltip Prostaglandin EP4 receptor
  • Antagonists: Grapiprant
  • GW-627368
  • L-161982
  • ONO-AE3-208
Unsorted
  • Agonists: 16,16-Dimethyl Prostaglandin E2
  • Aganepag
  • Carboprost
  • Evatanepag
  • Gemeprost
  • Nocloprost
  • Omidenepag
  • Prostaglandin F (dinoprost)
  • Simenepag
  • Taprenepag
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
  • Antagonists: RO1138452
TP (TXA2)Tooltip Thromboxane receptor
  • Agonists: Carbocyclic thromboxane A2
  • I-BOP
  • Thromboxane A2
  • U-46619
  • Vapiprost
Unsorted
  • Arbaprostil
  • Ataprost
  • Ciprostene
  • Clinprost
  • Cobiprostone
  • Delprostenate
  • Deprostil
  • Dimoxaprost
  • Doxaprost
  • Ecraprost
  • Eganoprost
  • Enisoprost
  • Eptaloprost
  • Esuberaprost
  • Etiproston
  • Fenprostalene
  • Flunoprost
  • Froxiprost
  • Lanproston
  • Limaprost
  • Luprostiol
  • Meteneprost
  • Mexiprostil
  • Naxaprostene
  • Nileprost
  • Nocloprost
  • Ornoprostil
  • Oxoprostol
  • Penprostene
  • Pimilprost
  • Piriprost
  • Posaraprost
  • Prostalene
  • Rioprostil
  • Rivenprost
  • Rosaprostol
  • Spiriprostil
  • Tiaprost
  • Tilsuprost
  • Tiprostanide
  • Trimoprostil
  • Viprostol
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
HQL-79
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators


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