Page last updated: 2024-12-11

stilbamidine

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Description

stilbamidine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5351747
CHEMBL ID142304
SCHEMBL ID208655
MeSH IDM0125618

Synonyms (35)

Synonym
4-[2-(4-carbamimidoylphenyl)vinyl]benzamidine
NCI35605
stilbamidinum
stilbamidine
4,4'-diamidinostilbene
stilbamidine [ban]
brn 3206434
4,4'-stilbenedicarboxamidine
einecs 204-519-5
ba 2652
benzamidine, 4,4'-vinylenedi-
diamidino stilbene
CHEMBL142304 ,
4-[(e)-2-(4-carbamimidoylphenyl)ethenyl]benzenecarboximidamide
4-((e)-2-{4-[(z)-amino(imino)methyl]phenyl}vinyl)benzenecarboximidamide
bdbm50210461
4,4''-(ethene-1,2-diyl)dibenzimidamide
(stilbamidine)4-[2-[4-amino(imino)methylphenyl]-(e)-1-ethenyl]phenyl-iminomethanamine
4-((e)-2-{4-[(z)-amino(imino)methyl]phenyl}vinyl)benzenecarboximidamide(stilbamidine isethionate)
CCG-36712
st31iio5ew ,
unii-st31iio5ew
4-09-00-03639 (beilstein handbook reference)
122-06-5
benzenecarboximidamide, 4,4'-(1,2-ethenediyl)bis-
stilbamidine [who-dd]
stilbamidine [mi]
SCHEMBL208655
4,4'-(1,2-ethanediyl)bisbenzenecarboximidamide
MMURVNDSFNJHAM-OWOJBTEDSA-N
CS-6597
HY-U00007
stilbamidin
Q27289385
AKOS040740925

Research Excerpts

Dosage Studied

The EC50 values calculated by means of dose-response curves were 45, 80, 165, 259 and 600 microM for 4', 6-diamidino-2-phenylindole (DAPI), dibromo propamidine, pentamidine 2-hydroxy stilbamidine and stil bamidine. No inhibitory effects on cell growth were found at 1 mM propamIDS, phenamIDS and amicarbalide.

ExcerptRelevanceReference
" 2,5-Bis(4-guanylphenyl)-1,3-oxazole and -1,3,4-thiadiazole showed good activity, whithout acute toxicity, against Trypanosoma rhodesiense in mice, producing cures at a 3 mg/kg dosage level."( Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
Boykin, DW; Das, BP; Wallace, RA, 1980
)
0.26
" The EC50 values calculated by means of dose-response curves were 45, 80, 165, 259 and 600 microM for 4', 6-diamidino-2-phenylindole (DAPI), dibromo propamidine, pentamidine 2-hydroxy stilbamidine and stilbamidine, respectively, although no inhibitory effects on cell growth were found at 1 mM propamidine, phenamidine and amicarbalide."( Putrescine uptake inhibition by aromatic diamidines in Leishmania infantum promastigotes.
Alvarez Bujidos, ML; Balaña Fouce, R; Cubria, JC; Ordoñez, D; Reguera, R, 1994
)
0.48
" The three most active salts were selected: [PtIVBr6]H2 (pentamidine); [PtIVBr6]H2 (stilbamidine), and [PtIVCl6]H2 (2-piperazinyl(1) ethyl amine), which induced growth-inhibition rates of more than 50% at 24 h of treatment and at the maximum dosage tested."( In vitro and in vivo activity of two Pt(IV) salts against leishmania donovani.
Craciunescu, D; Mesa-Valle, CM; Moraleda-Lindez, V; Osuna, A; Rodriguez-Cabezas, MN; Sanchez-Moreno, M, 1998
)
0.52
" Depending on the intended indication and dosing regimen, PPL can delay or stop development of a compound in the drug discovery process."( Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.
Gehlhaar, D; Greene, N; Johnson, TO; Pelletier, DJ; Tilloy-Ellul, A,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Protein arginine N-methyltransferase 5Homo sapiens (human)IC50 (µMol)378.05000.00900.69158.6000AID1128526; AID1506648
RmtAAspergillus nidulansIC50 (µMol)29.90005.90005.90005.9000AID286626
Protein arginine N-methyltransferase 1Homo sapiens (human)IC50 (µMol)207.37140.25003.61679.4000AID1128525; AID1506647; AID1685578; AID286629; AID527461; AID527462; AID527466
Protein arginine N-methyltransferase 1Homo sapiens (human)Ki30.30000.40001.05501.7100AID527646; AID527647
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
peptidyl-arginine N-methylationProtein arginine N-methyltransferase 5Homo sapiens (human)
spliceosomal snRNP assemblyProtein arginine N-methyltransferase 5Homo sapiens (human)
chromatin remodelingProtein arginine N-methyltransferase 5Homo sapiens (human)
DNA-templated transcription terminationProtein arginine N-methyltransferase 5Homo sapiens (human)
regulation of mitotic nuclear divisionProtein arginine N-methyltransferase 5Homo sapiens (human)
peptidyl-arginine methylationProtein arginine N-methyltransferase 5Homo sapiens (human)
circadian regulation of gene expressionProtein arginine N-methyltransferase 5Homo sapiens (human)
endothelial cell activationProtein arginine N-methyltransferase 5Homo sapiens (human)
negative regulation of gene expression via chromosomal CpG island methylationProtein arginine N-methyltransferase 5Homo sapiens (human)
negative regulation of cell differentiationProtein arginine N-methyltransferase 5Homo sapiens (human)
negative regulation of DNA-templated transcriptionProtein arginine N-methyltransferase 5Homo sapiens (human)
positive regulation of mRNA splicing, via spliceosomeProtein arginine N-methyltransferase 5Homo sapiens (human)
positive regulation of oligodendrocyte differentiationProtein arginine N-methyltransferase 5Homo sapiens (human)
regulation of ERK1 and ERK2 cascadeProtein arginine N-methyltransferase 5Homo sapiens (human)
Golgi ribbon formationProtein arginine N-methyltransferase 5Homo sapiens (human)
liver regenerationProtein arginine N-methyltransferase 5Homo sapiens (human)
regulation of signal transduction by p53 class mediatorProtein arginine N-methyltransferase 5Homo sapiens (human)
positive regulation of adenylate cyclase-inhibiting dopamine receptor signaling pathwayProtein arginine N-methyltransferase 5Homo sapiens (human)
regulation of DNA-templated transcriptionProtein arginine N-methyltransferase 5Homo sapiens (human)
regulation of DNA-templated transcriptionHistone-arginine methyltransferase CARM1Homo sapiens (human)
positive regulation of cell population proliferationHistone-arginine methyltransferase CARM1Homo sapiens (human)
methylationHistone-arginine methyltransferase CARM1Homo sapiens (human)
regulation of intracellular estrogen receptor signaling pathwayHistone-arginine methyltransferase CARM1Homo sapiens (human)
positive regulation of fat cell differentiationHistone-arginine methyltransferase CARM1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IHistone-arginine methyltransferase CARM1Homo sapiens (human)
response to cAMPHistone-arginine methyltransferase CARM1Homo sapiens (human)
replication fork reversalHistone-arginine methyltransferase CARM1Homo sapiens (human)
positive regulation of epithelial cell apoptotic processHistone-arginine methyltransferase CARM1Homo sapiens (human)
negative regulation of dendrite developmentHistone-arginine methyltransferase CARM1Homo sapiens (human)
peptidyl-arginine methylation, to asymmetrical-dimethyl arginineHistone-arginine methyltransferase CARM1Homo sapiens (human)
chromatin remodelingHistone-arginine methyltransferase CARM1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIProtein arginine N-methyltransferase 6Homo sapiens (human)
base-excision repairProtein arginine N-methyltransferase 6Homo sapiens (human)
regulation of mitochondrion organizationProtein arginine N-methyltransferase 6Homo sapiens (human)
methylationProtein arginine N-methyltransferase 6Homo sapiens (human)
protein modification processProtein arginine N-methyltransferase 6Homo sapiens (human)
regulation of megakaryocyte differentiationProtein arginine N-methyltransferase 6Homo sapiens (human)
negative regulation of DNA-templated transcriptionProtein arginine N-methyltransferase 6Homo sapiens (human)
cellular senescenceProtein arginine N-methyltransferase 6Homo sapiens (human)
regulation of signal transduction by p53 class mediatorProtein arginine N-methyltransferase 6Homo sapiens (human)
negative regulation of ubiquitin-dependent protein catabolic processProtein arginine N-methyltransferase 6Homo sapiens (human)
peptidyl-arginine methylation, to asymmetrical-dimethyl arginineProtein arginine N-methyltransferase 6Homo sapiens (human)
chromatin remodelingProtein arginine N-methyltransferase 6Homo sapiens (human)
in utero embryonic developmentProtein arginine N-methyltransferase 1Homo sapiens (human)
protein methylationProtein arginine N-methyltransferase 1Homo sapiens (human)
DNA damage responseProtein arginine N-methyltransferase 1Homo sapiens (human)
cell surface receptor signaling pathwayProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of cell population proliferationProtein arginine N-methyltransferase 1Homo sapiens (human)
RNA splicingProtein arginine N-methyltransferase 1Homo sapiens (human)
peptidyl-arginine methylationProtein arginine N-methyltransferase 1Homo sapiens (human)
viral protein processingProtein arginine N-methyltransferase 1Homo sapiens (human)
regulation of BMP signaling pathwayProtein arginine N-methyltransferase 1Homo sapiens (human)
neuron projection developmentProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of erythrocyte differentiationProtein arginine N-methyltransferase 1Homo sapiens (human)
regulation of megakaryocyte differentiationProtein arginine N-methyltransferase 1Homo sapiens (human)
negative regulation of megakaryocyte differentiationProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of translationProtein arginine N-methyltransferase 1Homo sapiens (human)
negative regulation of JNK cascadeProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of hemoglobin biosynthetic processProtein arginine N-methyltransferase 1Homo sapiens (human)
cardiac muscle tissue developmentProtein arginine N-methyltransferase 1Homo sapiens (human)
protein homooligomerizationProtein arginine N-methyltransferase 1Homo sapiens (human)
cellular response to methionineProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of p38MAPK cascadeProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of TORC1 signalingProtein arginine N-methyltransferase 1Homo sapiens (human)
positive regulation of double-strand break repair via homologous recombinationProtein arginine N-methyltransferase 1Homo sapiens (human)
chromatin remodelingProtein arginine N-methyltransferase 1Homo sapiens (human)
peptidyl-arginine methylation, to asymmetrical-dimethyl arginineProtein arginine N-methyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (35)

Processvia Protein(s)Taxonomy
p53 bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
transcription corepressor activityProtein arginine N-methyltransferase 5Homo sapiens (human)
protein bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
methyl-CpG bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
protein-arginine N-methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
protein-arginine omega-N symmetric methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
histone methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
identical protein bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
ribonucleoprotein complex bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
histone H4R3 methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
protein heterodimerization activityProtein arginine N-methyltransferase 5Homo sapiens (human)
E-box bindingProtein arginine N-methyltransferase 5Homo sapiens (human)
histone H3 methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
histone arginine N-methyltransferase activityProtein arginine N-methyltransferase 5Homo sapiens (human)
transcription cis-regulatory region bindingHistone-arginine methyltransferase CARM1Homo sapiens (human)
transcription coactivator activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
protein bindingHistone-arginine methyltransferase CARM1Homo sapiens (human)
beta-catenin bindingHistone-arginine methyltransferase CARM1Homo sapiens (human)
protein methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
histone arginine N-methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
protein-arginine N-methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
nuclear receptor coactivator activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
protein-arginine omega-N asymmetric methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
histone H3R17 methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
histone methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
lysine-acetylated histone bindingHistone-arginine methyltransferase CARM1Homo sapiens (human)
histone H3R2 methyltransferase activityHistone-arginine methyltransferase CARM1Homo sapiens (human)
DNA-binding transcription factor bindingHistone-arginine methyltransferase CARM1Homo sapiens (human)
chromatin bindingProtein arginine N-methyltransferase 6Homo sapiens (human)
protein bindingProtein arginine N-methyltransferase 6Homo sapiens (human)
histone arginine N-methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
protein-arginine N-methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
protein-arginine omega-N monomethyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
protein-arginine omega-N asymmetric methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
histone methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
histone bindingProtein arginine N-methyltransferase 6Homo sapiens (human)
histone H4R3 methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
histone H3R2 methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
histone H2AR3 methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
histone H3 methyltransferase activityProtein arginine N-methyltransferase 6Homo sapiens (human)
RNA bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
protein bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
N-methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
protein methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
methyl-CpG bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
protein-arginine N-methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
enzyme bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
protein-arginine omega-N monomethyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
protein-arginine omega-N asymmetric methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
histone methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
identical protein bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
histone H4R3 methyltransferase activityProtein arginine N-methyltransferase 1Homo sapiens (human)
mitogen-activated protein kinase p38 bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
GATOR1 complex bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
S-adenosyl-L-methionine bindingProtein arginine N-methyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusProtein arginine N-methyltransferase 5Homo sapiens (human)
nucleoplasmProtein arginine N-methyltransferase 5Homo sapiens (human)
Golgi apparatusProtein arginine N-methyltransferase 5Homo sapiens (human)
cytosolProtein arginine N-methyltransferase 5Homo sapiens (human)
methylosomeProtein arginine N-methyltransferase 5Homo sapiens (human)
chromatinProtein arginine N-methyltransferase 5Homo sapiens (human)
cytoplasmProtein arginine N-methyltransferase 5Homo sapiens (human)
histone methyltransferase complexProtein arginine N-methyltransferase 5Homo sapiens (human)
cytosolProtein arginine N-methyltransferase 5Homo sapiens (human)
nucleusProtein arginine N-methyltransferase 5Homo sapiens (human)
nuclear replication forkHistone-arginine methyltransferase CARM1Homo sapiens (human)
nucleusHistone-arginine methyltransferase CARM1Homo sapiens (human)
nucleoplasmHistone-arginine methyltransferase CARM1Homo sapiens (human)
cytoplasmHistone-arginine methyltransferase CARM1Homo sapiens (human)
cytosolHistone-arginine methyltransferase CARM1Homo sapiens (human)
nucleusProtein arginine N-methyltransferase 6Homo sapiens (human)
nucleoplasmProtein arginine N-methyltransferase 6Homo sapiens (human)
nucleolusProtein arginine N-methyltransferase 6Homo sapiens (human)
lysosomal membraneProtein arginine N-methyltransferase 1Homo sapiens (human)
nucleusProtein arginine N-methyltransferase 1Homo sapiens (human)
nucleoplasmProtein arginine N-methyltransferase 1Homo sapiens (human)
cytoplasmProtein arginine N-methyltransferase 1Homo sapiens (human)
cytosolProtein arginine N-methyltransferase 1Homo sapiens (human)
methylosomeProtein arginine N-methyltransferase 1Homo sapiens (human)
nucleusProtein arginine N-methyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (87)

Assay IDTitleYearJournalArticle
AID110812Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 40 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1685578Inhibition of PRMT1 (unknown origin)2021RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1
Pharmacophore-based screening of diamidine small molecule inhibitors for protein arginine methyltransferases.
AID527466Inhibition of human GST-tagged PRMT1-mediated arginine methylation expressed in Escherichia coli BL21 (DE3) using H4(1-20) and [14C]-AdoMet by scintillation counting2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID1136527Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 640 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID1146859Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 160 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID110814Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 5 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
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]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID286632Hypomethylation of arginine on histone H4 in HepG2 cells at 50 uM by Western blot2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID110805Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 160 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID1124314Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 6.5 mg/kg, po treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID110802Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 10 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID110806Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 2.5 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID527649Inhibition of HAT p300-mediated arginine methylation assessed as residual activity at 1 mM using H4(1-20) and [14C]-acetyl CoA by scintillation counting2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID1136521Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 10 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID1124305Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 106 mg/kg, po treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
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.
AID1124311Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 13.3 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID286634Reduction of arginine methylation on histone H3 in HepG2 cells at 50 uM2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID527647Binding affinity to His6x-tagged PRMT1 expressed in Escherichia coli BL21 (DE3) using fluorescein-labeled H4(1-11) peptide by spectrofluorimeter analysis2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID1146855Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 10 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1124308Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 53 mg/kg, po treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID1124299Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 424 mg/kg, po treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID1136523Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 40 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID1124309Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 26.5 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
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]
AID286629Inhibition of human recombinant PRMT1 by TRF assay2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1506648Inhibition of PRMT5 (unknown origin) assessed as reduction in methyl transfer from [3H]-SAM to biotinylated histone H4 peptide H4-20-Biotin pre-incubated for 3 mins before [3H]-SAM addition and measured after 45 mins by scintillation proximity assay2017MedChemComm, Feb-01, Volume: 8, Issue:2
Discovery of Decamidine as a New and Potent PRMT1 Inhibitor.
AID1128527Inhibition of GST-tagged CARM1 (unknown origin) using [3H]SAM and histone H3.1 as substrate at 20 uM after 1 hr by P81 filter binding assay2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Diamidine compounds for selective inhibition of protein arginine methyltransferase 1.
AID1124307Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 53 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID396382Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 by [3H]hypoxanthine uptake2008European journal of medicinal chemistry, Dec, Volume: 43, Issue:12
Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.
AID1136520Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 5 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
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]
AID1124304Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 106 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID1136524Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 80 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID53470Inhibitory dose against oncornaviral DNA polymerase activity of moloney murine leukemia virus1980Journal of medicinal chemistry, Jul, Volume: 23, Issue:7
Diaryl amidine derivatives as oncornaviral DNA polymerase inhibitors.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1124301Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 212 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID110818Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 80 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID1146856Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 20 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID110807Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 20 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
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]
AID527646Inhibition of His6x-tagged PRMT1-mediated arginine methylation expressed in Escherichia coli BL21 (DE3) using H4(1-11) and [14C]-SAM by scintillation counting2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1128526Inhibition of HA-tagged recombinant PRMT5 (unknown origin) expressed in HEK293T cells using [3H]SAM and histone H4 (1 to 20) as substrate after 8 mins by P81 filter binding assay2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Diamidine compounds for selective inhibition of protein arginine methyltransferase 1.
AID527461Inhibition of His6x-tagged PRMT1-mediated protein arginine methylation expressed in Escherichia coli BL21 (DE3) using H4(1-20) and [14C]-SAM by scintillation counting2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
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]
AID1136519Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 2.5 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID540236Phospholipidosis-positive literature compound observed in human
AID1136525Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 160 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID26757DNA binding dissociation constant as KD; No data1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics.
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]
AID527462Inhibition of His6x-tagged PRMT1-mediated protein arginine methylation expressed in Escherichia coli BL21 (DE3) using GAR R4 peptide and [14C]-AdoMet by scintillation counting2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID286633Hypomethylation of arginine on histone H4 in HepG2 cells at 25 uM by Western blot2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1124302Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 212 mg/kg, po treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID588208Literature-mined public compounds from Lowe et al phospholipidosis modelling dataset2010Molecular pharmaceutics, Oct-04, Volume: 7, Issue:5
Predicting phospholipidosis using machine learning.
AID1146852Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 2.5 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID527471Binding affinity to PRMT1 expressed in Escherichia coli BL21 (DE3) using fluorescein-labeled GAR R4 peptide by spectrofluorimeter analysis2010Journal of medicinal chemistry, Aug-26, Volume: 53, Issue:16
Discovery and mechanistic study of a class of protein arginine methylation inhibitors.
AID1128525Inhibition of His6x-tagged recombinant PRMT1 (unknown origin) expressed in Escherichia coli BL21(DE3) using [3H]SAM and histone H4 (1 to 20) as substrate after 8 mins by P81 filter binding assay2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Diamidine compounds for selective inhibition of protein arginine methyltransferase 1.
AID286630Inhibition methylation of R3 in histone H4 in HepG2 cells2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1146860Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 320 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1506647Inhibition of PRMT1 (unknown origin) assessed as reduction in methyl transfer from [3H]-SAM to biotinylated histone H4 peptide H4-20-Biotin at 10 uM pre-incubated for 3 mins before [3H]-SAM addition and measured after 15 mins by scintillation proximity as2017MedChemComm, Feb-01, Volume: 8, Issue:2
Discovery of Decamidine as a New and Potent PRMT1 Inhibitor.
AID286637Inhibition of estradiol-mediated ERalpha activation in MCF-7-2a cells at 150 uM2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1146857Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 40 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1128528Inhibition of His6x-tagged PRMT6 (unknown origin) using [3H]SAM and histone H3.1 as substrate at 20 uM after 1 hr by P81 filter binding assay2014Journal of medicinal chemistry, Mar-27, Volume: 57, Issue:6
Diamidine compounds for selective inhibition of protein arginine methyltransferase 1.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID286626Inhibition of Aspergillus nidulans RmtA by TRF assay2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1146854Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 5 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1124298Antiplasmodial activity against Trypanosoma brucei rhodesiense Wellcome CT infected in ICR/HA mouse assessed as curated mouse at 424 mg/kg, sc treated within 2 hrs of parasite infection measured up to 30 days1979Journal of medicinal chemistry, Apr, Volume: 22, Issue:4
A new chemical series active against African trypanosomes: benzyltriphenylphosphonium salts.
AID1146858Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 80 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1136526Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 320 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID286631Hypomethylation of arginine on histone H4 in HepG2 cells at 150 uM by Western blot2007Journal of medicinal chemistry, May-17, Volume: 50, Issue:10
Target-based approach to inhibitors of histone arginine methyltransferases.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID110811Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 320 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID1136522Antitrypanosomal activity against Trypanosoma rhodesiense CT infected in ICR/HA Swiss mouse assessed as 30-day increase in survival time at 20 mg/kg relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans.
AID110801Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 1.25 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID1146861Antitrypanosomal activity against Trypanosoma rhodesiense infected in mouse assessed as increase in survival time by 30 days at 640 mg/kg relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)thiophenes and -pyrroles.
AID110817Tested for antiTrypanosomal activity against Trypanosoma rhodesiense in mice at dose of 640 mg/kg expressed as mean survival time (MST) or cures1980Journal of medicinal chemistry, May, Volume: 23, Issue:5
Synthesis and antitrypanosomal activity of some bis(4-guanylphenyl) five- and six-membered ring heterocycles.
AID496825Antimicrobial activity against Leishmania mexicana2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (138)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990122 (88.41)18.7374
1990's5 (3.62)18.2507
2000's5 (3.62)29.6817
2010's5 (3.62)24.3611
2020's1 (0.72)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.98

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 Index19.98 (24.57)
Research Supply Index5.02 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other151 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]