Page last updated: 2024-12-05

fenoprofen

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

Description

Fenoprofen is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is a propionic acid derivative and acts by inhibiting the enzyme cyclooxygenase (COX), which is responsible for the production of prostaglandins, substances that cause pain, fever, and inflammation. Fenoprofen is used to treat a variety of conditions, including osteoarthritis, rheumatoid arthritis, and dysmenorrhea. It is available in oral and topical formulations. Fenoprofen is generally well-tolerated, but it can cause gastrointestinal side effects such as nausea, dyspepsia, and ulceration. It can also increase the risk of cardiovascular events, including heart attack and stroke. Fenoprofen is studied to better understand its mechanisms of action, potential benefits and risks, and its role in the management of various inflammatory and painful conditions.'

Fenoprofen: A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fenoprofen : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. [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]

Cross-References

ID SourceID
PubMed CID3342
CHEMBL ID1297
CHEBI ID5004
SCHEMBL ID3797
MeSH IDM0008332

Synonyms (132)

Synonym
AB00052197-04
benzeneacetic acid, .alpha.-methyl-3-phenoxy-, (.+/-.)-
DIVK1C_000848
KBIO1_000848
2-[3-(phenyloxy)phenyl]propanoic acid
SPECTRUM_001252
PRESTWICK3_000754
nalfon
(+-)-m-phenoxyhydratropic acid
fenoprofenum [inn-latin]
fenoprofene [inn-french]
hydratropic acid, m-phenoxy-, (+-)-
einecs 250-850-3
(+-)-2-(3-phenoxyphenyl)propionic acid
hsdb 3328
brn 2118687
lilly 53838
benzeneacetic acid, alpha-methyl-3-phenoxy-, (+-)-
fenoprofeno [inn-spanish]
SPECTRUM5_001311
PRESTWICK2_000754
BPBIO1_000846
BSPBIO_000768
IDI1_000848
AB00052197
31879-05-7
fenoprofen
C06997
(+/-)-fenoprofen
3-phenoxyhydratropic acid
(+/-)-2-(3-phenoxyphenyl)propionic acid
2-(3-phenoxyphenyl)propionic acid
alpha-methyl-3-phenoxybenzeneacetic acid
alpha-(m-phenoxyphenyl)propionic acid
dl-2-(3-phenoxyphenyl)propionic acid
DB00573
(+/-)-m-phenoxyhydratropic acid
2-(m-phenoxyphenyl)propionic acid
D02350
fenoprofen (usan/inn)
NCGC00094887-02
NCGC00094887-01
KBIOGR_001477
KBIO3_001860
KBIOSS_001732
KBIO2_004300
KBIO2_006868
KBIO2_001732
NINDS_000848
PRESTWICK1_000754
SPECTRUM2_001391
SPECTRUM4_001009
PRESTWICK0_000754
SPBIO_002707
SPECTRUM3_000910
SPBIO_001402
SPECTRUM1501011
HMS2092B07
HMS2090G18
nsc-757813
lilly-53858
CHEMBL1297 ,
fenoprofenum
fenoprofeno
CHEBI:5004 ,
fenoprofene
2-(3-phenoxyphenyl)propanoic acid
HMS502K10
HMS1921B19
AKOS005256238
NCGC00094887-03
pharmakon1600-01501011
nsc757813
CCG-39009
feneprofen calcium salt dihydrate
di-benzeneacetate, .alpha.-methyl-3-phenoxy-, calcium salt, dihydrate
einecs 249-770-1
unii-ra33eac7ky
ra33eac7ky ,
29679-58-1
fenoprofen [usan:inn:ban]
nsc 757813
lilly 53858
benzeneacetic acid, |a-methyl-3-phenoxy-
EPITOPE ID:139975
gtpl4820
fenoprofen [who-dd]
fenoprofen [vandf]
fenoprofen [mi]
fenoprofen [inn]
fenoprofen [hsdb]
fenoprofen [usan]
benzeneacetic acid, .alpha.-methyl-3-phenoxy-
SCHEMBL3797
alpha-(m-phenoxyphenyl)-propionic acid
3-phenoxy-hydratropic acid
2-(3-phenoxy-phenyl)-propionic acid
2-(3-phenoxyphenyl)-propionic acid
calcium;2-(3-phenoxyphenyl)propionic acid;hydrate
calcium;2-(3-phenoxyphenyl)propanoic acid;hydrate
bdbm54705
cid_16219353
2-(3-phenoxyphenyl)propanoic acid #
hydratropic acid, m-phenoxy-, (.+/-.)-
(.+/-.)-m-phenoxyhydratropic acid
AB00052197_05
AB00052197_06
DTXSID9023045 ,
mfcd00072027
sr-05000001767
SR-05000001767-1
benzeneacetic acid, ?-methyl-3-phenoxy-
J-018559
SBI-0051632.P002
STL554715
(2r)-2-(3-phenoxyphenyl)propanoic acid
Q2555245
AS-30559
BBL100921
benzeneacetic acid, alpha-methyl-3-phenoxy-
A875776
3-(4-phenoxyphenyl)propionic acid,98%
EN300-124340
HY-B1456A
CS-W019775
alpha-dl-2-(3-phenoxyphenyl)propionic acid
(+-)-m-phenoxyhydrotropic acid
fenoprofene (inn-french)
fenoprofenum (inn-latin)
m01ae04
dtxcid503045
fenoprofeno (inn-spanish)

Research Excerpts

Overview

Fenoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) against rheumatoid arthritis, degenerative joint disease, ankylosing spondylitis and gout. It is a chiral non-steroid antiinflammatory drug, marketed as a racemic mixture of its R(-) and S(+) enantiomers.

ExcerptReferenceRelevance
"Fenoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) against rheumatoid arthritis, degenerative joint disease, ankylosing spondylitis and gout. "( Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity.
Hey-Hawkins, E; Laube, M; Lönnecke, P; Maksimović-Ivanić, D; Mijatović, S; Mojić, M; Pietzsch, J; Useini, L, 2023
)
2.66
"Fenoprofen is a non-steroidal anti-inflammatory drug (NSAID), available in several different countries, but not widely used."( Single dose oral fenoprofen for acute postoperative pain in adults.
Derry, S; Moore, RA; Traa, MX, 2011
)
2.15
"Fenoprofen (FPF) is a chiral non-steroid antiinflammatory drug, marketed as a racemic mixture of its R(-) and S(+) enantiomers. "( Chiral inversion of fenoprofen in horses and dogs: an in vivo-in vitro study.
Benoit, E; Delatour, P; Jaussaud, P; Soraci, A, 1996
)
2.06
"Fenoprofen calcium (FC) is a nonsteroidal, anti-inflammatory, analgesic, and antipyretic agent. "( Dehydration, hydration behavior, and structural analysis of fenoprofen calcium.
Kidd, C; Long, S; Varlashkin, P; Xu, J; Zhu, H, 2001
)
2

Effects

ExcerptReferenceRelevance
"Fenoprofen has compared favourably with phenylbutazone in osteoarthrosis of the hips and with aspirin in osteoarthrosis of the shoulders, hips, knees and spine."( Fenoprofen: a review of its pharmacological properties and therapeutic efficacy in rheumatic diseases.
Avery, GS; Brogden, RN; Pinder, RM; Speight, TM, 1977
)
2.42

Actions

ExcerptReferenceRelevance
"Fenoprofen was found to inhibit the formation of palmitoyl-CoA in both microsomal and peroxisomal fractions whereas the formation of lignoceroyl-CoA and cerotoyl-CoA was not inhibited at all."( Studies on the effect of fenoprofen on the activation and oxidation of long chain and very long chain fatty acids in hepatocytes and subcellular fractions from rat liver.
Lageweg, W; Wanders, RJ, 1993
)
1.31

Toxicity

ExcerptReferenceRelevance
" No serious adverse effects were encountered."( Fenoprofen calcium in steroid treated rheumatoid arthritis: efficacy, safety, and steroid-sparing effect.
Blechman, WJ; Zane, S, 1976
)
1.7
" In this work, the antinociceptive and toxic effects of two new coordination complexes: Cu₂(fen)₄(caf)₂ [fen: fenoprofenate anion; caf: caffeine] and Cu₂(fen)₄(dmf)₂ [dmf: N-N'-dimethylformamide] were evaluated in mice."( Anti-nociceptive activity and toxicity evaluation of Cu(II)-fenoprofenate complexes in mice.
Agotegaray, M; Bras, C; Gandini, NA; Gumilar, F; Minetti, A; Quinzani, O, 2012
)
0.83
"Many adverse drug reactions are caused by the cytochrome P450 (CYP)-dependent activation of drugs into reactive metabolites."( Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
Jones, LH; Nadanaciva, S; Rana, P; Will, Y, 2016
)
0.43

Pharmacokinetics

ExcerptReferenceRelevance
" The bioavailability parameters Cmax, tmax, and AUC0--12 hr for the drug in plasma were consistent with a linear pharmacokinetic model, as were the amounts of fenoprofen and hydroxyfenoprofen excreted in the urine."( Linear pharmacokinetics of orally administered fenoprofen calcium.
Bechtol, LD; Bopp, RJ; Bunde, CA; Farid, KZ; Nash, JF; Spradlin, CT, 1979
)
0.71
" The development of NSAIDs having safer therapeutic profile depends on the better understanding of their mechanisms, physicochemical and pharmacokinetic properties."( Self-organizing molecular field analysis of NSAIDs: assessment of pharmacokinetic and physicochemical properties using 3D-QSPkR approach.
Kumar, M; Sinha, VR; Thareja, S, 2012
)
0.38

Compound-Compound Interactions

ExcerptReferenceRelevance
"The influence of albumin towards the metabolism behavior of fenoprofen enantiomers and relevant drug-drug interaction was investigated in the present study."( Albumin Supplement Affects the Metabolism and Metabolism-Related Drug-Drug Interaction of Fenoprofen Enantiomers.
Chen, JW; Meng, Y; Wang, F; Wang, JX; Wang, N; Yang, GH, 2015
)
0.88

Bioavailability

Free access to hay significantly reduced the peak plasma concentration and bioavailability of fenoprofen. Large interindividual differences in absorption and elimination pattern occurred.

ExcerptReferenceRelevance
"The bioavailability of fenoprofen from three different fenoprofen calcium capsule formulations containing the equivalent of 60, 165, and 300 mg of fenoprofen was determined in two studies."( Linear pharmacokinetics of orally administered fenoprofen calcium.
Bechtol, LD; Bopp, RJ; Bunde, CA; Farid, KZ; Nash, JF; Spradlin, CT, 1979
)
0.83
" The absorption rate and the correlation between pH and membrane diffusion rate constant were investigated in vitro using the "Sartorius" apparatus."( Biopharmaceutical investigation of fenoprofen.
Kéri, E; Marton, S; Plachy, J; Rácz, I, 1987
)
0.55
" This procedure has been used for routine assay of multiple samples from bioavailability and compliance studies."( High-performance liquid chromatographic assay for fenoprofen in human plasma.
Bopp, RJ; Farid, KZ; Nash, JF, 1981
)
0.52
" Free access to hay significantly reduced the peak plasma concentration and bioavailability of fenoprofen, and large interindividual differences in absorption and elimination pattern occurred."( Disposition of human drug preparations in the horse. IV. Orally administered fenoprofen.
Debackere, M; Delbeke, FT; Landuyt, J, 1995
)
0.74
" The lower Cl(T)/f of (-)-(R)-FEN observed for patients with rheumatoid arthritis is consistent with lower clearance by inversion, although other metabolic pathways, drug interactions, and bioavailability of the individual enantiomers may also contribute to the difference."( Influence of rheumatoid arthritis in the enantioselective disposition of fenoprofen.
Barissa, GR; Donadi, EA; Dos Reis, ML; Lanchote, VL; Poggi, JC, 2004
)
0.56
" The relative bioavailability of the selected gum tablet was found to be 166."( Immediate release three-layered chewing gum tablets of fenoprofen calcium: preparation, optimization and bioavailability studies in healthy human volunteers.
Abdelbary, AA; Amin, MM; El Assassy, AE, 2012
)
0.63

Dosage Studied

The S/R ratio of fenoprofen in plasma always exceeds 1 and increases with time after dosage. The ratio of its 4'-hydroxy metabolite remains almost unchanged at 1.

ExcerptRelevanceReference
"The determination of drug-protein binding parameters (n's and K's) can lead to important information on the required therapeutic dosage regimen and possible clinical complications associated with competitive displacement of one drug by a concurrently administered agent."( Comparison of graphical and computerized methods for calculating binding parameters for two strongly bound drugs to human serum albumin.
Perrin, JH; Vallner, JJ; Wold, S, 1976
)
0.26
" These data show linearity of kinetics for fenoprofen in plasma throughout the 60--300-mg dosage range after a single dose."( Linear pharmacokinetics of orally administered fenoprofen calcium.
Bechtol, LD; Bopp, RJ; Bunde, CA; Farid, KZ; Nash, JF; Spradlin, CT, 1979
)
0.78
"Several fenoprofen salts were prepared to obtain the most acceptable form for an oral dosage formulation."( Fenoprofen: drug form selection and preformulation stability studies.
Brannon, JL; Hirsch, CA; Messenger, RJ, 1978
)
2.14
" The pyrogram enables the identification of the drug to be achieved as the pure compound, in a formulated dosage form or excreted in urine."( The identification of ibuprofen and analogues in urine by pyrolysis gas chromatography mass spectrometry.
Irwin, WJ; Slack, JA, 1978
)
0.26
" At the dosage level employed, no significant differences were noted between the two anti-inflammatory agents in regard to efficacy."( Fenoprofen in rheumatoid arthritis: a controlled crossover multi-centre study.
Gum, OB, 1976
)
1.7
" Of the 510 urines collected from 102 individuals during these dosage regimens, two gave false-positive tests for cannabinoid by enzyme-mediated immunoassay (EMIA), one after 1200 mg of ibuprofen in three divided doses for one day and one in a patient taking naproxyn on a chronic basis; none was falsely positive for benzodiazepines."( Investigation of interference by nonsteroidal anti-inflammatory drugs in urine tests for abused drugs.
Jennison, TA; Jones, G; Rollins, DE, 1990
)
0.28
" When this type of drug fails to provide relief for a woman suffering from primary dysmenorrhea, switching to another NSAID may be more appropriate than increasing the dosage and the probability of dosage-related side effects."( Efficacy of fenoprofen in the treatment of primary dysmenorrhea.
Burt, RA; Caldwell, BV; Kaul, AF; Naftolin, F; Osathanondh, R; Scavone, JM; Sokoloff, BJ; White, RM, 1985
)
0.65
"This paper evaluates the dose-response relationship of several doses of fenoprofen calcium, between 12."( Dose response to fenoprofen calcium using placebo and codeine as controls.
Gruber, CM; Offen, WW, 1985
)
0.84
" Initial fenoprofen dosage was 900 mg/m2/d increased to 1800 mg/m2/d (3200 mg/d-max)."( Aspirin and fenoprofen (Nalfon) in the treatment of juvenile rheumatoid arthritis results of the double blind-trial. A segment II study.
Baum, J; Bernstein, B; Brewer, EJ; Emery, HM; Fink, CW; Giannini, EH; Schaller, JG,
)
0.93
"Studies were conducted on postpartum and postoperative patients to estimate the dose-response line of fenoprofen and to contrast it with codeine and placebo."( Fenoprofen and codeine analgesia.
Laska, EM; Sunshine, A, 1981
)
1.92
" Dosage and side effect information, in particular, cannot be reliably extrapolated from data derived from studies in adults."( The position of the pharmaceutical industry in the development of drugs for pediatric use.
Christensen, CN, 1980
)
0.26
" 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]

Roles (6)

RoleDescription
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
antipyreticA drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
drug allergenAny drug which causes the onset of an allergic reaction.
[role 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]

Drug Classes (1)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy group.
[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]

Pathways (1)

PathwayProteinsCompounds
Fenoprofen Action Pathway2967

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)2.73000.00032.177410.0000AID1397088
Prostaglandin G/H synthase 1Homo sapiens (human)IC50 (µMol)0.14500.00021.557410.0000AID625243
Prostaglandin G/H synthase 2Ovis aries (sheep)IC50 (µMol)26.30000.00101.453910.0000AID1397089
Lactoylglutathione lyaseHomo sapiens (human)Ki388.66670.00122.59479.1400AID568008; AID568009; AID604299
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin G/H synthase 1Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 1Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 1Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 1Homo sapiens (human)
regulation of cell population proliferationProstaglandin G/H synthase 1Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 1Homo sapiens (human)
carbohydrate metabolic processLactoylglutathione lyaseHomo sapiens (human)
regulation of transcription by RNA polymerase IILactoylglutathione lyaseHomo sapiens (human)
glutathione metabolic processLactoylglutathione lyaseHomo sapiens (human)
methylglyoxal metabolic processLactoylglutathione lyaseHomo sapiens (human)
osteoclast differentiationLactoylglutathione lyaseHomo sapiens (human)
negative regulation of apoptotic processLactoylglutathione lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 1Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 1Homo sapiens (human)
protein bindingProstaglandin G/H synthase 1Homo sapiens (human)
heme bindingProstaglandin G/H synthase 1Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 1Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 1Homo sapiens (human)
lactoylglutathione lyase activityLactoylglutathione lyaseHomo sapiens (human)
protein bindingLactoylglutathione lyaseHomo sapiens (human)
zinc ion bindingLactoylglutathione lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
photoreceptor outer segmentProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 1Homo sapiens (human)
Golgi apparatusProstaglandin G/H synthase 1Homo sapiens (human)
intracellular membrane-bounded organelleProstaglandin G/H synthase 1Homo sapiens (human)
extracellular exosomeProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 1Homo sapiens (human)
nucleoplasmLactoylglutathione lyaseHomo sapiens (human)
cytoplasmLactoylglutathione lyaseHomo sapiens (human)
cytosolLactoylglutathione lyaseHomo sapiens (human)
plasma membraneLactoylglutathione lyaseHomo sapiens (human)
extracellular exosomeLactoylglutathione lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (79)

Assay IDTitleYearJournalArticle
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1397089Inhibition of ovine COX2 assessed as reduction in PGH2 production by enzyme immunoassay2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Synthesis and biological properties of aryl methyl sulfones.
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
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
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.
AID1211792Hepatic clearance in human2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
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.
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]
AID1636440Drug activation in human Hep3B cells assessed as human CYP2D6-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 300 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of NA2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1744122Inhibition of human ACMSD assessed as picolinic acid level at 1 mM by HPLC analysis (Rvb = 83.6 +/- 3.1%)2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Diflunisal Derivatives as Modulators of ACMS Decarboxylase Targeting the Tryptophan-Kynurenine Pathway.
AID1636357Drug activation in human Hep3B cells assessed as human CYP3A4-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 300 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of NA2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID677462Dissociation constant, pKa of the compound2012European journal of medicinal chemistry, Jul, Volume: 53Self-organizing molecular field analysis of NSAIDs: assessment of pharmacokinetic and physicochemical properties using 3D-QSPkR approach.
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]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' 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.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID625287Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatomegaly2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1397088Inhibition of ovine COX1 assessed as reduction in PGH2 production by enzyme immunoassay2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Synthesis and biological properties of aryl methyl sulfones.
AID624619Specific activity of expressed human recombinant UGT2B72000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID373867Hepatic clearance in human hepatocytes in absence of fetal calf serum2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
First-principle, structure-based prediction of hepatic metabolic clearance values in human.
AID1211791Fraction unbound in human hepatocytes2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID625284Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic failure2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1211795Dissociation constant, pKa of the compound2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID1397090Selectivity ratio of IC50 for ovine COX1 to IC50 for ovine COX22018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Synthesis and biological properties of aryl methyl sulfones.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
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]
AID624608Specific activity of expressed human recombinant UGT1A42000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID625283Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for elevated liver function tests2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625282Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cirrhosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
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]
AID625281Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholelithiasis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID625285Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic necrosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1211796Intrinsic clearance in cryopreserved human HepaRG cells assessed per 10'6 cells by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID1211798Intrinsic clearance in human using well stirred liver model by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID1744121Inhibition of human ACMSD assessed as QUIN level at 1 mM by HPLC analysis (Rvb = 16.4 +/- 2.9%)2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Diflunisal Derivatives as Modulators of ACMS Decarboxylase Targeting the Tryptophan-Kynurenine Pathway.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1211793Lipophilicity, log P of the compound2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID568009Inhibition of glyoxalase 12011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Identification of curcumin derivatives as human glyoxalase I inhibitors: A combination of biological evaluation, molecular docking, 3D-QSAR and molecular dynamics simulation studies.
AID297158Inhibition of CXCL1-induced cell migration in human PMN cells at 0.01 uM by chemotaxis assay2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2.
AID624607Specific activity of expressed human recombinant UGT1A32000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID624615Specific activity of expressed human recombinant UGT2B102000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID625288Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for jaundice2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID624612Specific activity of expressed human recombinant UGT1A92000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1636496Drug activation in human Hep3B cells assessed as human CYP2C9-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 71.3 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of N2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID515780Intrinsic solubility of the compound in water2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
QSAR-based solubility model for drug-like compounds.
AID625280Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholecystitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1211797Intrinsic clearance in cryopreserved human hepatocytes cells assessed per 10'6 cells by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID625286Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID624641Inhibition of 4-methylumbelliferone glucuronidation by human UGT enzymes from liver microsomes2005Pharmacology & therapeutics, Apr, Volume: 106, Issue:1
UDP-glucuronosyltransferases and clinical drug-drug interactions.
AID263728Drug level in mouse plasma at 50 mg/kg, po2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.
AID624606Specific activity of expressed human recombinant UGT1A12000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
AID625290Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver fatty2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625289Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver disease2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID297157Inhibition of CXCL8-induced cell migration in human PMN cells at 0.01 uM by chemotaxis assay2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID625279Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for bilirubinemia2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID263727Drug level in mouse brain at 50 mg/kg, po2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.
AID263729Ratio of drug level in brain against plasma in mice at 50 mg/kg, po2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.
AID604299Inhibition of human glyoxalase 12011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Structural investigation into the inhibitory mechanisms of indomethacin and its analogues towards human glyoxalase I.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID625291Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver function tests abnormal2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID624618Specific activity of expressed human recombinant UGT2B42000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID568008Inhibition of human recombinant His-tagged glyoxalase 1 expressed in Escherichia coli BL21 (DE3) preincubated for 20 mins by Dixon plot analysis2011Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3
Identification of curcumin derivatives as human glyoxalase I inhibitors: A combination of biological evaluation, molecular docking, 3D-QSAR and molecular dynamics simulation studies.
AID625292Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) combined score2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
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]
AID1211794Fraction unbound in blood (not specified)2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
Comparison of cryopreserved HepaRG cells with cryopreserved human hepatocytes for prediction of clearance for 26 drugs.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1346932Human SMCT1 (Sodium iodide symporter, sodium-dependent multivitamin transporter and sodium-coupled monocarboxylate transporters)2006Pharmaceutical research, Jun, Volume: 23, Issue:6
Interaction of ibuprofen and other structurally related NSAIDs with the sodium-coupled monocarboxylate transporter SMCT1 (SLC5A8).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (295)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990180 (61.02)18.7374
1990's39 (13.22)18.2507
2000's34 (11.53)29.6817
2010's36 (12.20)24.3611
2020's6 (2.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 50.71

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index50.71 (24.57)
Research Supply Index5.92 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index83.50 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (50.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials60 (19.17%)5.53%
Reviews20 (6.39%)6.00%
Case Studies43 (13.74%)4.05%
Observational0 (0.00%)0.25%
Other190 (60.70%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]