Pirprofen

Pirprofen
Systematic (IUPAC) name

2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoic acid
Identifiers
CAS Number	31793-07-4^N
ATC code	M01AE08
PubChem	CID 35935
ChemSpider	33051^Y
UNII	T7KN291890^Y
KEGG	D05515^Y
ChEMBL	CHEMBL188952^Y
Chemical data
Formula	C₁₃H₁₄ClNO₂
Molar mass	251.70876 g/mol
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)

Pirprofen was a non-steroidal anti-inflammatory drug 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.^[1]^:223

References

↑ 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 Consolidated List of Products - Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments, Twelfth Issue - Pharmaceuticals.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	Aminophenazone Ampyrone Azapropazone Clofezone 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 Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indomethacin Indomethacin farnesil Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tolmetin Zomepirac^†

Oxicams	Ampiroxicam Droxicam Lornoxicam Meloxicam Piroxicam Tenoxicam

Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ COX-inhibiting nitric oxide donator: Naproxcinod

N-Arylanthranilic acids (fenamates)	Azapropazone Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin

Coxibs	Apricoxib Celecoxib 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

Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.

Prostanoid signaling

Receptor
(ligands)

DP (D₂)

DP₁	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant

DP₂	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 OC-459 OC000459 QAV-680 Ramatroban Setipiprant TM30089 Vidupiprant

EP (E₂)

EP₁	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322

EP₂	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155

EP₃	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Sulprostone Antagonists: L-798106

EP₄	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: GW-627368 L-161982 ONO-AE3-208

Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Antagonists: 12-HETE
13-APA
AA-2414
Argatroban
Bay U3405
BMS-180,291
Daltroban
Domitroban
EP-045
GR-32191
ICI-185282
ICI-192605
Ifetroban
Imitrodast
L-655240
L-670596
Linotroban
Mipitroban
ONO-3708
ONO-11120
Picotamide
Pinane thromboxane A₂
Ramatroban
Ridogrel
S-145
Samixogrel
Seratrodast
SQ-28,668
SQ-29,548
Sulotroban
Terbogrel
Terutroban
TRA-418

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)	Aceclofenac Acemetacin Acetanilide Alclofenac Alminoprofen Aloxiprin AM404 Amfenac Ampiroxicam Anitrazafen Antrafenine Apricoxib Aspirin (acetylsalicylic acid) Azapropazone Bendazac Benorilate (benorylate) Benoxaprofen Bromfenac Bucetin Bucloxic acid (blucloxate) Bufexamac Bumadizone Butibufen Carbasalate calcium Carprofen Celecoxib Cimicoxib Cinmetacin Clobuzarit Clometacin Clonixeril Clonixin Curcumin Deracoxib Dexibuprofen Dexindoprofen Dexketoprofen Diclofenac Difenpiramide Diflunisal Dipyrocetyl Droxicam DuP-697 Enolicam Ethenzamide Etodolac Etofenamate Etoricoxib Felbinac Fenbufen Fenclofenac Fenoprofen Fentiazac Firocoxib FK-3311 Floctafenic acid (floctafenate) Floctafenine Flosulide Flufenamic acid (flufenamate) Flumizole Flunixin Flunoxaprofen Fluproquazone Flurbiprofen FR-122047 Glafenine Glimepiride Glucametacin Guacetisal Hyperforin Ibuprofen Ibuproxam Indometacin farnesil Indometacin (indomethacin) Indoprofen Isoxicam Itazigrel Ketoprofen Ketorolac L-655240 L-670596 Licofelone Lonazolac Lornoxicam Loxoprofen Lumiracoxib Magnesium salicylate Mavacoxib Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Meloxicam Menatetrenone (vitamin K₂) Mesalazine (5-aminosalicylic acid) Methyl salicylate Miroprofen Mofezolac Morniflumate Nabumetone Naproxcinod Naproxen NCX-466 NCX-4040 Niflumic acid (niflumate) Nimesulide NS-398 Oxametacin Oxaprozin Oxindanac Pamicogrel Paracetamol (acetaminophen) Parapropamol Parecoxib Phenacetin Piroxicam Pirprofen Polmacoxib Pranoprofen Proglumetacin Propacetamol Resveratrol Robenacoxib Rofecoxib Romazarit Rutecarpine Salacetamide Salicin Salicylamide Salicylic acid (salicylate) Salsalate Satigrel SC-236 SC-560 SC-58125 Sodium salicylate Sulindac Sulindac sulfide Suprofen Talinflumic acid (talinflumate) Tarenflurbil Tenidap Tenoxicam Tepoxalin Tiaprofenic acid (tiaprofenate) Tiflamizole Tilmacoxib Timegadine Tolfenamic acid (tolfenamate) Tolmetin Trifenagrel Triflusal Tropesin Valdecoxib Vedaprofen Zidometacin Zomepirac

PGD₂ synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGE synthase	HQL-79

PGF synthase	Bimatoprost

PGI₂ synthase	Tranylcypromine

TXA synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Leukotrienergics

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