Page last updated: 2024-12-05

hydroxystilbamidine

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

Description

hydroxystilbamidine: minor descriptor (63-86); on-line & INDEX MEDICUS search STILBAMIDINES (66-86); RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5284571
CHEMBL ID1301
CHEBI ID135161
SCHEMBL ID108492
MeSH IDM0263277

Synonyms (36)

Synonym
39j262e49w ,
hidroxiestilbamidina
BRD-K62186992-334-01-0
4-[(e)-2-{4-[amino(imino)methyl]phenyl}ethenyl]-3-hydroxybenzenecarboximidamide
hydroxystilbamidine
495-99-8
NCGC00166289-01
2-hydroxy-4,4'-stilbenedicarboxamidine
2-hydroxy-4,4'-diguanylstilbene
oxistilbamidinum
CHEBI:135161
CHEMBL1301
NCGC00166289-02
hydroxystilbamidine [mi]
hydroxystilbamidine [who-dd]
hydroxystilbamidine [inn]
SCHEMBL108492
cid_5494031
(4e)-4-[2-[4-[bis(azanyl)methylidene]cyclohexa-2,5-dien-1-ylidene]ethylidene]-3-oxidanylidene-cyclohexa-1,5-diene-1-carboximidamide;2-oxidanylethanesulfonic acid
(4e)-4-[2-[4-(diaminomethylene)cyclohexa-2,5-dien-1-ylidene]ethylidene]-3-keto-cyclohexa-1,5-diene-1-carboxamidine;2-hydroxyethanesulfonic acid
(4e)-4-[2-[4-(diaminomethylidene)cyclohexa-2,5-dien-1-ylidene]ethylidene]-3-oxocyclohexa-1,5-diene-1-carboximidamide;2-hydroxyethanesulfonic acid
(4e)-4-[2-[4-(diaminomethylidene)-1-cyclohexa-2,5-dienylidene]ethylidene]-3-oxo-1-cyclohexa-1,5-dienecarboximidamide;2-hydroxyethanesulfonic acid
bdbm58125
4-[(e)-2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzene-1-carboximidamide
(e)-4-(4-carbamimidoylstyryl)-3-hydroxybenzimidamide
1071752-67-4
DTXSID80873552
DB14753
Q65034878
(e)-hydroxystilbamidine
ohsa
4-(4-carbamimidoylstyryl)-3-hydroxybenzimidamide
4-[(e)-2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzenecarboximidamide
EN300-18567329
4-[2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzene-1-carboximidamide
AKOS040760002

Research Excerpts

Dosage Studied

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency28.18380.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency30.30010.000811.382244.6684AID686978; AID686979
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.58490.035520.977089.1251AID504332
flap endonuclease 1Homo sapiens (human)Potency28.18380.133725.412989.1251AID588795
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency35.48130.050127.073689.1251AID588590
DNA polymerase kappa isoform 1Homo sapiens (human)Potency56.23410.031622.3146100.0000AID588579
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency36.12540.005612.367736.1254AID624032
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency19.95260.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (56)

Assay IDTitleYearJournalArticle
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1124807Inhibition of mouse hippocampal neurons ASIC transfected in CHO cells assessed as inhibition of acid-evoked current at -60 mV holding potential by two-electrode voltage-clamp electrophysiology assay2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
Some non-conventional biomolecular targets for diamidines. A short survey.
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.
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.
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.
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.
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.
AID1130852Anti-leukemic activity against mouse L1210 cells allografted in ip dosed DBA2 mouse assessed as increase in host lifespan administered qd for 1 to 4 days1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
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.
AID1130854Binding affinity to DNA (unknown origin) assessed as decrease in velocity of L1210 DNA-dependent DNA polymerase reaction1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID1079945Animal toxicity known. [column 'TOXIC' 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]
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.
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.
AID1130855Displacement of ethidium from poly[d(A-T)]-poly[d(A-T)] DNA (unknown origin) by fluorimetric assay1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
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]
AID1130853Anti-leukemic activity against mouse L1210 cells allografted in ip dosed DBA2 mouse assessed as optimum drug dose required for the effect administered qd for 1 to 4 days1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
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.
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.
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.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' 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]
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.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
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.
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]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
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.
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.
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.
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.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' 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.
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.
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.
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]
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
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.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1130856Displacement of ethidium from poly[d(G-C)]-poly[d(G-C)] DNA (unknown origin) by fluorimetric assay1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Potential antitumor agents. 31. Quantitative structure-activity relationships for the antileukemic bis(guanylhydrazones).
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.
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.
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.
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.
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.
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.
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.
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.
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.
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]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (56)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (80.36)18.7374
1990's2 (3.57)18.2507
2000's5 (8.93)29.6817
2010's4 (7.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (7.69%)6.00%
Case Studies1 (1.54%)4.05%
Observational0 (0.00%)0.25%
Other59 (90.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]