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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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

[1]

[2]

[3]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives ( profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids ( fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib ( +tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^# WHO-Essential Medicines; ^† withdrawn drugs; ^‡ veterinary use.
category commons portal

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives ( profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids ( fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib ( +tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^# WHO-Essential Medicines; ^† withdrawn drugs; ^‡ veterinary use.
category commons portal

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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)