Page last updated: 2024-12-05

glafenine

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Description

Glafenine is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is a derivative of 2-phenylpropionic acid. Glafenine was synthesized in the 1960s and was initially marketed as an analgesic. However, its use was restricted due to reports of hepatotoxicity. Glafenine acts as an inhibitor of cyclooxygenase (COX), an enzyme involved in the production of prostaglandins, which are involved in inflammation and pain. It has been studied for its potential therapeutic benefits in conditions such as osteoarthritis, rheumatoid arthritis, and acute pain. However, due to its hepatotoxic effects, it is no longer widely used.'

Glafenine: An anthranilic acid derivative with analgesic properties used for the relief of all types of pain. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

glafenine : A carboxylic ester that is 2,3-dihydroxypropyl anthranilate in which the amino group is substituted by a 7-chloroquinolin-4-yl group. A non-steroidal anti-inflammatory drug, glafenine and its hydrochloride salt were used for the relief of all types of pain, but high incidence of anaphylactic reactions resulted in their withdrawal from the market. [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 CID3474
CHEMBL ID146095
CHEBI ID31653
SCHEMBL ID24246
MeSH IDM0009256

Synonyms (109)

Synonym
glafenine [inn:dcf:jan]
alicidon
anthranilic acid, n-(7-chloro-4-quinolyl)-, 2,3-dihydroxypropyl ester
glycerylaminophenaquine
glaphenin
einecs 223-315-7
4-(2'-beta,gamma-dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline
4-((2-carboxyphenyl)amino)-7-chloroquinoline alpha-monoglyceride
dolomate
2,3-dihydroxypropyl n-(7-chloro-4-quinolyl) anthranilate
privadol
glicafan
benzoic acid, 2-((7-chloro-4-quinolinyl)amino)-, 2,3-dihydroxypropyl ester
adalgur [french]
glifanan
glaphenine
brn 0497124
4-(2'-(beta,gamma-dihydroxypropoxycarbonyl)phenylamino)-7-chloroquinoleine [french]
glafenin
r 1707
glifan
glafeninum [inn-latin]
glafenina [inn-spanish]
glifanar
BRD-A38076815-003-03-8
KBIO1_000295
DIVK1C_000295
SPECTRUM_001212
glafenine
UNM000003519201
BPBIO1_000250
SMP1_000140
IDI1_000295
PRESTWICK2_000293
BCBCMAP01_000138
PRESTWICK3_000293
OPREA1_338301
BSPBIO_003124
AB00052189
glafenine (jan/inn)
3820-67-5
D01351
BSPBIO_000226
SPECTRUM5_001564
NCGC00094881-01
NCGC00094881-02
KBIO2_004260
KBIO2_006828
KBIO2_001692
KBIO3_002344
KBIOSS_001692
KBIOGR_001379
PRESTWICK1_000293
SPECTRUM3_001422
SPECTRUM4_000830
PRESTWICK0_000293
SPECTRUM2_001383
SPBIO_001366
SPBIO_002445
NINDS_000295
SPECTRUM1500996
NCGC00094881-04
NCGC00094881-03
nsc-757808
r-1707
CHEMBL146095
CHEBI:31653 ,
glafenina
glafeninum
2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate
HMS500O17
FT-0668976
HMS1921O18
pharmakon1600-01500996
nsc757808
AKOS016012374
CCG-39001
unii-46hl4i09ah
adalgur
46hl4i09ah ,
4-(2'-(beta,gamma-dihydroxypropoxycarbonyl)phenylamino)-7-chloroquinoleine
nsc 757808
1-glyceryl n-(7-chloro-4-quinolyl)anthranilate
EPITOPE ID:131799
SCHEMBL24246
glafenine [mart.]
glafenine [mi]
glafenine [who-dd]
glafenine [jan]
glafenine [inn]
CS-4757
DTXSID1048546
2,3-dihydroxypropyl 2-((7-chloroquinolin-4-yl)amino)benzoate
GWOFUCIGLDBNKM-UHFFFAOYSA-N
2,3-dihydroxypropyl 2-[(7-chloro-4-quinolinyl)amino]benzoate
HY-B1153
AB00052189_09
AB00052189_08
SR-01000473478-4
glafenine, analytical standard
bdbm50103508
SBI-0051624.P002
Q5566483
FS-6628
SB17236
2,3-dihydroxypropyl 2-(((7-chloroquinolin-4-yl)amino)benzoate
D86844
1-glyceryl n-[7-chloro-4-quinolyl]anthranilate hydrochloride
2,3-dihydroxypropyl2-(((7-chloroquinolin-4-yl)amino)benzoate

Research Excerpts

Overview

Glafenine is a widely prescribed analgesic drug, and shock is one of its severe side-effects.

ExcerptReferenceRelevance
"Glafenine is a widely prescribed analgesic drug, and shock is one of its severe side-effects."( [Shock caused by glafenine. Apropos of 7 complications].
Boutchnei, T; Davido, A; Hallali, P,
)
1.19

Effects

ExcerptReferenceRelevance
"As glafenine hydrochloride has the ability to fully inhibit proliferation and to partially inhibit migration in haSMCs, it could be an interesting substance for further research in the field of restenosis therapy."( Impact of glafenine hydrochloride on human endothelial cells and human vascular smooth muscle cells: a substance reducing proliferation, migration and extracellular matrix synthesis.
Claussen, CD; Duda, SH; Kehlbach, R; Muringaseril, M; Rodegerdts, E; Schöber, W; Tran, QB; Wiesinger, B; Wiskirchen, J, 2003
)
1.24

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

Bioavailability

ExcerptReferenceRelevance
"The bioavailability and gastric ulcerogenic activity of oxyphenbutazone and glafenine (acidic and basic nonsteroidal anti-inflammatory drugs), coated with different cellulose derivatives were assessed in albino rats."( A new approach to encapsulating nonsteroidal anti-inflammatory drugs. IV. Effect of cellulose derivatives with different functional groups on the bioavailability and gastric ulcerogenic activity of acidic as well as basic nonsteroidal anti-inflammatory dr
el-Dien, EZ; Luzzi, LA; Meshali, MM; Omar, SA,
)
0.36
" The two drugs were found to have the same efficiency on the subjective parameters but high bioavailability glaphenine seems to have an effectiveness in the range of articulatory movements, which is not found with paracetamol."( Comparative study of high bio-availability glaphenine and paracetamol in cervical and lumbar arthrosis.
Albert, A; Crielaard, JM; Franchimont, P; Urbin Choffray, D, 1987
)
0.27
" One promising therapeutic approach is to identify drugs that have been developed for other indications but that also correct the CFTR trafficking defect, thereby exploiting their known safety and bioavailability in humans and reducing the time required for clinical development."( Correction of the Delta phe508 cystic fibrosis transmembrane conductance regulator trafficking defect by the bioavailable compound glafenine.
Balghi, H; Carlile, GW; de Jonge, HR; Hanrahan, JW; Kus, B; Lesimple, P; Liao, J; Liu, N; Robert, R; Rotin, D; Scholte, BJ; Thomas, DY; Wilke, M, 2010
)
0.57

Dosage Studied

New thin layer densitometry and high performance liquid chromatography (HPLC) methods are described for quantitative determination of glafenine in dosage forms in the presence of its photo-degradation products.

ExcerptRelevanceReference
" A dosage of 400 mg/day is adequate for an opinion of the efficacy of the product to be made, with the average dosage is about 150 mg/day (1/2 table x 3 times a day)."( [Therapy of headaches. Apropos of 87 cases].
Chappon, C,
)
0.13
"05) and its longer half-life would lead to an accumulation if the usual dosage regimen was prescribed for CP and could result in nephrotoxicity."( Pharmacokinetics of glafenine and glafenic acid in patients with cirrhosis, compared to healthy volunteers.
Fauvelle, F; Kusielewicz, D; Nicolas, P; Perret, G; Petitjean, O; Tod, M; Vermerie, N, 1992
)
0.61
"Two women aged 62 and 69 years who had been taking glafenine at normal dosage over a period of 4 years developed a renal calculus."( [Renal pelvis stones made of glafenic acid in two patients under prolonged treatment with analgesics (author's transl)].
Amar, E; Daudon, M; Pottier, J; Protat, MF; Réveillaud, RJ; Rymer, M, 1980
)
0.51
"New thin layer densitometry and high performance liquid chromatography (HPLC) methods are described for quantitative determination of glafenine in dosage forms in the presence of its photo-degradation products and in serum in the presence of its metabolites."( Determination of glafenine in dosage forms and serum by thin layer densitometry and high performance liquid chromatography.
Abbas, AB; Elnemma, EM; Hassan, SS, 1997
)
0.84
" 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 (3)

RoleDescription
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
inhibitorA substance that diminishes the rate of a chemical 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 (5)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
glycolA diol in which the two hydroxy groups are on different carbon atoms, usually but not necessarily adjacent.
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
aminoquinolineAny member of the class of quinolines in which the quinoline skeleton is substituted by one or more amino or substituted-amino groups.
[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]

Protein Targets (28)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency35.48130.177814.390939.8107AID2147
Chain A, CruzipainTrypanosoma cruziPotency31.62280.002014.677939.8107AID1476
USP1 protein, partialHomo sapiens (human)Potency50.11870.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency20.73290.000811.382244.6684AID686978; AID686979
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
mitogen-activated protein kinase 1Homo sapiens (human)Potency15.84890.039816.784239.8107AID995
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency7.94330.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency7.94331.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpRattus norvegicus (Norway rat)IC50 (µMol)32.20000.40002.75008.6000AID1209456
Bile salt export pumpHomo sapiens (human)IC50 (µMol)18.61500.11007.190310.0000AID1209455; AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (57)

Assay IDTitleYearJournalArticle
AID1124467Acute toxicity in po dosed CD1 mouse after 7 days1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
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.
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.
AID109659General behavior in mice after oral administration (1000 mg/kg) using acute toxicity assay; Normal1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones.
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.
AID1124468Analgesic activity in po dosed CD1 mouse assessed as inhibition of acetic acid-induced writhing administered 30 mins prior to acetic acid challenge measured after 15 mins1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
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.
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.
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]
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.
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.
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]
AID183317Anti-inflammatory effect expressed as % inhibition at 50 mg/kg in acute carrageenan paw edema test in rats1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones.
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).
AID1124470Analgesic activity in po dosed OF1 mouse assessed as dose required to double paw licking reaction time after 30 mins by hot plate test1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
AID1209457Unbound Cmax in human plasma2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
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.
AID678720Metabolic stability in human liver microsomes assessed as low signal/noise ratio (S/N of 1 to 10) 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.
AID112942Analgesic activity in mice using p-phenylquinone test.1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones.
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.
AID119946Percent mortality in mice after oral administration (1000 mg/kg) using acute toxicity assay1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones.
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.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' 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.
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]
AID1209455Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1209456Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake2012Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 40, Issue:1
In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' 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
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' 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.
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.
AID1764405Agonist activity at Gal4-fused human Nurr1 LBD expressed in HEK293T cells co-expressing firefly luciferase assessed as luciferase activity at 10 uM incubated for 12 to 14 hrs by hybrid reporter gene assay2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Fragment-like Chloroquinolineamines Activate the Orphan Nuclear Receptor Nurr1 and Elucidate Activation Mechanisms.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
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.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID468443Inhibition of human FAAH at 1 uM2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
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]
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]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' 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).
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.
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.
AID1124469Antiinflammatory activity in po dosed CD1 mouse assessed as inhibition of carrageenan-induced paw edema administered 1 hr prior to carrageenan challenge measured after 3 hrs1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
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.
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.
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.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (151)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990103 (68.21)18.7374
1990's15 (9.93)18.2507
2000's8 (5.30)29.6817
2010's22 (14.57)24.3611
2020's3 (1.99)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.68

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 Index31.68 (24.57)
Research Supply Index5.25 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (6.18%)5.53%
Reviews9 (5.06%)6.00%
Case Studies57 (32.02%)4.05%
Observational0 (0.00%)0.25%
Other101 (56.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]