pirprofen

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 464208014

| IUPAC_name = 2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoic acid

| image = Pirprofen.png

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 31793-07-4

| ATC_prefix = M01

| ATC_suffix = AE08

| PubChem = 35935

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 33051

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T7KN291890

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05515

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 188952

| C=13 | H=14 | Cl=1 | N=1 | O=2

| smiles = O=C(O)C(c1cc(Cl)c(cc1)N2C/C=C\C2)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PIDSZXPFGCURGN-UHFFFAOYSA-N

}}

Pirprofen was a nonsteroidal anti-inflammatory drug (NSAID){{cite journal | vauthors = Todd PA, Beresford R | title = Pirprofen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy | journal = Drugs | volume = 32 | issue = 6 | pages = 509–37 | date = December 1986 | pmid = 3539573 | doi = 10.2165/00003495-198632060-00003 | s2cid = 195692709 }} 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.{{cite journal | vauthors = Depla AC, Vermeersch PH, van Gorp LH, Nadorp JH | title = Fatal acute liver failure associated with pirprofen. Report of a case and a review of the literature | journal = The Netherlands Journal of Medicine | volume = 37 | issue = 1–2 | pages = 32–6 | date = August 1990 | pmid = 2215831 | doi = | url = }} Ciba-Geigy voluntarily withdrew the drug from the market worldwide in 1990.WHO. [https://web.archive.org/web/20141108142051/http://apps.who.int/medicinedocs/en/d/Js16780e/ 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{{rp|223}}