Pirprofen

Pirprofen
Clinical data
ATC code	M01AE08 (WHO) ;
Identifiers
	IUPAC name 2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoic acid;
CAS Number	31793-07-4 ;
PubChem CID	35935;
ChemSpider	33051 ;
UNII	T7KN291890;
KEGG	D05515 ;
ChEMBL	ChEMBL188952 ;
CompTox Dashboard (EPA)	DTXSID7023489 ;
ECHA InfoCard	100.046.172
Chemical and physical data
Formula	C13H14ClNO2
Molar mass	251.71 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
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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

^ 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.
^ 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.
^ 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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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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[Todd_1986-1] 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.

[Depla_1990-2] 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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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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[2]

[3]

Clinical data

ATC code	M01AE08 (WHO)
Identifiers
IUPAC name 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^Y
UNII	T7KN291890
KEGG	D05515^Y
ChEMBL	ChEMBL188952^Y
CompTox Dashboard (EPA)	DTXSID7023489
ECHA InfoCard	100.046.172
Chemical and physical data
Formula	C₁₃H₁₄ClNO₂
Molar mass	251.71 g·mol⁻¹
3D model (JSmol)	Interactive image
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)