Page last updated: 2024-12-06

pirprofen

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Pirprofen is a nonsteroidal anti-inflammatory drug (NSAID) that was originally developed in the 1970s. It works by inhibiting the enzyme cyclooxygenase (COX), which is involved in the production of prostaglandins, chemicals that cause inflammation, pain, and fever. Pirprofen was initially marketed for the treatment of pain and inflammation associated with rheumatoid arthritis and osteoarthritis. However, it was later withdrawn from the market due to concerns about its potential for liver toxicity and gastrointestinal side effects. Research on pirprofen continues to explore its potential for use in treating other conditions, such as cancer and Alzheimer's disease. Pirprofen has been shown to exhibit anti-tumor activity in some studies, and it may also have neuroprotective properties.'

pirprofen: anti-inflammatory agent used in therapy of rheumatoid arthritis; prostaglandin synthetase inhibitor; more potent than indomethacin; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID35935
CHEMBL ID188952
CHEBI ID135028
SCHEMBL ID24311
MeSH IDM0053200

Synonyms (44)

Synonym
su-21524
rengasil
2-[3-chloro-4-(2,5-dihydro-1h-pyrrol-1-yl)phenyl]propanoic acid
hydratropic acid, 3-chloro-4-(3-pyrrolin-1-yl)-
einecs 250-805-8
pirprofenum [inn-latin]
benzeneacetic acid, 3-chloro-4-(2,5-dihydro-1h-pyrrol-1-yl)-alpha-methyl-
pirprofeno [inn-spanish]
su 21524
pirprofene [inn-french]
brn 1686438
3-chloro-4-(3-pyrrolin-1-yl)hydratropic acid
pirprofen (usan/inn)
D05515
31793-07-4
pirprofen
CHEBI:135028
2-[3-chloro-4-(2,5-dihydropyrrol-1-yl)phenyl]propanoic acid
seflenyl
CHEMBL188952
racemic pirprofen
rangasil 400
t7kn291890 ,
5-20-04-00276 (beilstein handbook reference)
pirprofen [usan:inn:ban]
pirprofene
unii-t7kn291890
pirprofenum
pirprofeno
pirprofen [jan]
(+/-)-pirprofen
pirprofen [inn]
pirprofen [mi]
2-(3-chloro-4-(2,5-dihydropyrrol-1-yl)-phenyl)propanoic acid
pirprofen [usan]
46801-03-0
pirprofen [mart.]
2-(3-chloro-4-(3-pyrrolin-1-yl)phenyl)propionic acid
benzeneacetic acid, 3-chloro-4-(2,5-dihydro-1h-pyrrol-1-yl)-.alpha.-methyl-
pirprofen [who-dd]
SCHEMBL24311
DTXSID7023489
Q3905662
DB13722

Research Excerpts

Overview

Pirprofen is a new non-steroidal anti-inflammatory drug. It is related structurally to drugs such as ibuprofen, ketoprofen and naproxen.

ExcerptReferenceRelevance
"Pirprofen is a new non-steroidal anti-inflammatory drug. "( [Pharmacological study of pirprofen].
Cohen, M, 1982
)
2.01
"Pirprofen is a non-steroidal anti-inflammatory drug, related structurally to drugs such as ibuprofen, ketoprofen and naproxen. "( Pirprofen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.
Beresford, R; Todd, PA, 1986
)
3.16

Effects

ExcerptReferenceRelevance
"Pirprofen has an apparent elimination half-life of about 7 hr."( Disposition of pirprofen, a new anti-inflammatory drug.
Bartlett, F; Egger, H; Gaito, MJ; Gum, OB; Li, C; Luders, RC; Maggio-Cavaliere, MB; Resnick, O; Soo, A, 1977
)
1.33
"Pirprofen has an apparent elimination half-life of about 7 hr."( Disposition of pirprofen, a new anti-inflammatory drug.
Bartlett, F; Egger, H; Gaito, MJ; Gum, OB; Li, C; Luders, RC; Maggio-Cavaliere, MB; Resnick, O; Soo, A, 1977
)
1.33

Toxicity

ExcerptReferenceRelevance
" An understanding of structure-activity relationships (SARs) of chemicals can make a significant contribution to the identification of potential toxic effects early in the drug development process and aid in avoiding such problems."( Developing structure-activity relationships for the prediction of hepatotoxicity.
Fisk, L; Greene, N; Naven, RT; Note, RR; Patel, ML; Pelletier, DJ, 2010
)
0.36

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetics of pirprofen in these children were compared to the pharmacokinetic parameter values obtained in healthy volunteers and in elderly arthritic adults receiving 400 mg of pirprofen."( Pharmacokinetics of pirprofen in children with juvenile chronic arthritis.
Dubois, JP; Gioud-Paquet, M; Hallé, F; Lenoir, G; Marfil, F; Prieur, AM; Sioufi, A,
)
0.76
" and the pharmacokinetic profile of the drug and the metabolite was calculated."( Pharmacokinetics of pirprofen and its pyrrol metabolite in elderly patients.
Balladore, GE; Bichisao, E; Ferrario, P; Ferrero, M; Fraschini, F; Maresca, V; Monza, GC; Rossi, FA; Zecca, L, 1988
)
0.6

Compound-Compound Interactions

ExcerptReferenceRelevance
"A study of pirprofen (rengasil) combined with small doses of corticosteroids in 93 patients with rheumatoid arthritis during a double blind multicentre testing showed good and satisfactory therapeutic results in 60%."( [Study of pirprofen (rengasil) combined with maintenance doses of corticosteroids in rheumatoid arthritis in a double-blind multicenter trial].
Alekberova, ZS; Kobaladze, SG; Pokryshkin, VI; Taletene, IP; Trofimova, TM, 1986
)
1.06

Bioavailability

Pirprofen was well absorbed by man, rhesus monkey, rat, and mouse after oral administration of a solution of 14C-labeled compound.

ExcerptReferenceRelevance
"Pirprofen was well absorbed by man, rhesus monkey, rat, and mouse after oral administration of a solution of 14C-labeled compound."( Metabolism of pirprofen in man, monkey, rat, and mouse.
Bartlett, F; Egger, H; Karliner, J; Yuan, HP,
)
1.93
" The rate of absorption decreased significantly when pirprofen was administered as a capsule in comparison with a solution."( Absorption kinetics and model characteristics of orally administered pirprofen.
Gerardin, A; Luders, RC; Wagner, WE, 1983
)
0.75
" The absolute bioavailability of the active S-enantiomer (78."( Influence of the route of administration on the pharmacokinetics of pirprofen enantiomers in the rat.
Brocks, DR; Jamali, F; Liang, WT, 1993
)
0.52

Dosage Studied

Pirprofen proved more active than pentazocin. In three female rats which were dosed with 10 mg/kg racemic pirprofen orally, plasma concentrations of the enantiomers could be followed for 24 h.

ExcerptRelevanceReference
" In the multicentre study, a further 80 athletes were treated with a variable dosage (600-1200 mg/day) until the disappearance of symptoms, but for no longer than 2 weeks."( Pirprofen in the treatment of sports injuries.
Azzolini, V; Braconaro, F; Garagiola, U; Giani, E; Maresca, V; Porretti, E; Ventura, A; Volpi, P,
)
1.57
" Repeated dosing increased plasma drug concentrations in both groups but the extent was as predicted from the single dose data."( Pharmacokinetics of pirprofen in young volunteers and elderly patients.
Hosie, J; John, VA; Kendall, MJ; Main, A; Rooney, L, 1985
)
0.59
" The recommended dosage in osteoarthritis is 450-600 mg/d."( Pirprofen.
Dionne, RE; Weber, SS, 1983
)
1.71
" At either of the two dosage levels, pirprofen proved more active than pentazocin."( [A study of the analgesic effects of pirprofen after oral surgery].
Sperr, W, 1982
)
0.81
" The binding characteristics of these drugs were not altered when plasma containing either warfarin or tolbutamide at concentrations equivalent to those expected normally after therapeutic dosing were concomitantly spiked with therapeutic amounts of pirprofen."( Effect of pirprofen on protein binding of warfarin and tolbutamide in human plasma.
Chao, D; Luders, RC, 1981
)
0.85
" No significant differences were detected between the enantiomers after oral or iv dosing in t1/2, Vd, or sigma Xu."( Influence of the route of administration on the pharmacokinetics of pirprofen enantiomers in the rat.
Brocks, DR; Jamali, F; Liang, WT, 1993
)
0.52
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrrolineAny organic heteromonocyclic compound with a structure based on a dihydropyrrole.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID678717Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-benzyloxyquinoline as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID625293Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in LTKB-BD2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID243647In vitro inhibitory activity against ovine cyclooxygenase-1 (COX-1) at 200 uM; Inactive2004Journal of medicinal chemistry, Sep-23, Volume: 47, Issue:20
Novel cyclooxygenase-1 inhibitors discovered using affinity fingerprints.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID625295Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in Pfizer data2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID678712Inhibition of human CYP1A2 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using ethoxyresorufin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID678719Metabolic stability in human liver microsomes assessed as medium signal/noise ratio (S/N of 10 to 100) by measuring GSH adduct formation at 100 uM after 90 mins by HPLC-MS analysis2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID678722Covalent binding affinity to human liver microsomes assessed per mg of protein at 10 uM after 60 mins presence of NADPH2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID678716Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using diethoxyfluorescein as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID678714Inhibition of human CYP2C19 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 3-butyryl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID678713Inhibition of human CYP2C9 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-methoxy-4-trifluoromethylcoumarin-3-acetic acid as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID588209Literature-mined public compounds from Greene et al multi-species hepatotoxicity modelling dataset2010Chemical research in toxicology, Jul-19, Volume: 23, Issue:7
Developing structure-activity relationships for the prediction of hepatotoxicity.
AID588210Human drug-induced liver injury (DILI) modelling dataset from Ekins et al2010Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 38, Issue:12
A predictive ligand-based Bayesian model for human drug-induced liver injury.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID678715Inhibition of human CYP2D6 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 4-methylaminoethyl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID625276FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of most concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (113)

TimeframeStudies, This Drug (%)All Drugs %
pre-199091 (80.53)18.7374
1990's13 (11.50)18.2507
2000's2 (1.77)29.6817
2010's7 (6.19)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.56 (24.57)
Research Supply Index5.24 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials53 (39.55%)5.53%
Reviews4 (2.99%)6.00%
Case Studies14 (10.45%)4.05%
Observational0 (0.00%)0.25%
Other63 (47.01%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]