Page last updated: 2024-11-04

4-aminobenzamidine

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

Description

4-Aminobenzamidine is a synthetic compound that acts as a potent inhibitor of the enzyme trypanothione reductase. Trypanothione reductase is a critical enzyme in the antioxidant defense system of trypanosomes, which are parasitic protozoa responsible for diseases like African trypanosomiasis. The inhibition of trypanothione reductase by 4-aminobenzamidine disrupts the parasite's ability to combat oxidative stress, leading to its death. This makes 4-aminobenzamidine a promising lead compound for the development of new drugs to treat trypanosomiasis. It is currently being investigated for its potential therapeutic applications, including its effectiveness against other parasitic infections. Its synthesis involves a multi-step process, starting with the reaction of 4-nitrobenzamidine with hydrazine hydrate to yield 4-aminobenzamidine.'

4-aminobenzamidine: a urokinase inhibitor; inhibits acrosin; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1725
CHEMBL ID124632
SCHEMBL ID150756
MeSH IDM0049099

Synonyms (48)

Synonym
AKOS005444850
unii-63gk9kt599
63gk9kt599 ,
nsc-227928
nsc227928
3858-83-1
brn 0386209
4-aminobenzenecarboximidamide
nsc 227928
einecs 223-370-7
4-aminobenzamidine
benzamidine, p-amino-
benzenecarboximidamide, 4-amino-
lopac-a-7148
NCGC00015084-01
LOPAC0_000070
STK367857
p-aminobenzamidine
ABD ,
NCGC00162057-01
NCGC00015084-03
bdbm50092660
CHEMBL124632 ,
4-amino-benzamidine
inchi=1/c7h9n3/c8-6-3-1-5(2-4-6)7(9)10/h1-4h,8h2,(h3,9,10)
wpanetawygdrll-uhfffaoysa-
BBL007616
CCG-204165
NCGC00015084-02
4-aminobenzene-1-carboximidamide
4-aminobenzamidine-d4 dihydrochloride
AB00374717-08
SCHEMBL150756
WPANETAWYGDRLL-UHFFFAOYSA-N
4-aminobenzimidamide
DTXSID30191899
NCGC00015084-04
FT-0768066
1185995-47-4
1329499-33-3
p-aminobenzamidine . 2 hcl
SDCCGSBI-0050058.P002
NCGC00015084-05
Q27263611
(6s)-tetrahydro-l-biopterin-d3 disulfate
4-aminobenzimidamide? (dabigatran impurity pound(c)
CS-0165920
EN300-70197

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Thus, 2-aminobenzimidazoles may have improved pharmacokinetic properties which could increase the bioavailability of inhibitors which contain this moiety."( Identification of novel inhibitors of urokinase via NMR-based screening.
Boyd, S; Davidson, D; Fesik, SW; Hajduk, PJ; Nettesheim, D; Nienaber, V; Rockway, T; Severin, J; Smith, R, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" Linear dose-response curves were obtained and gave ED50 values (50% inhibition of fertilization) of 230 microM for BD, 27 microM for ABD, 35 nM for MUGB, and 13 nM for NPGB."( Inhibition of in-vitro fertilization of mouse gametes by proteinase inhibitors.
Beyler, SA; Zaneveld, LJ, 1982
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
dopamine D1 receptorHomo sapiens (human)Potency0.01840.00521.30228.1995AID624455
ThrombopoietinHomo sapiens (human)Potency7.94330.02517.304831.6228AID917; AID918
regulator of G-protein signaling 4Homo sapiens (human)Potency37.68580.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency33.58750.035520.977089.1251AID504332
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency11.20150.00106.000935.4813AID943; AID944
[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)
Urokinase-type plasminogen activatorHomo sapiens (human)IC50 (µMol)7.00000.03703.385910.0000AID215985
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
positive regulation of cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
response to hypoxiaUrokinase-type plasminogen activatorHomo sapiens (human)
proteolysisUrokinase-type plasminogen activatorHomo sapiens (human)
chemotaxisUrokinase-type plasminogen activatorHomo sapiens (human)
signal transductionUrokinase-type plasminogen activatorHomo sapiens (human)
blood coagulationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of signaling receptor activityUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
negative regulation of plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
smooth muscle cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of smooth muscle cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell adhesion mediated by integrinUrokinase-type plasminogen activatorHomo sapiens (human)
urokinase plasminogen activator signaling pathwayUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell population proliferationUrokinase-type plasminogen activatorHomo sapiens (human)
fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
negative regulation of fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of wound healingUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of smooth muscle cell-matrix adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityUrokinase-type plasminogen activatorHomo sapiens (human)
protein bindingUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
extracellular regionUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular spaceUrokinase-type plasminogen activatorHomo sapiens (human)
plasma membraneUrokinase-type plasminogen activatorHomo sapiens (human)
focal adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
external side of plasma membraneUrokinase-type plasminogen activatorHomo sapiens (human)
cell surfaceUrokinase-type plasminogen activatorHomo sapiens (human)
specific granule membraneUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular exosomeUrokinase-type plasminogen activatorHomo sapiens (human)
tertiary granule membraneUrokinase-type plasminogen activatorHomo sapiens (human)
serine protease inhibitor complexUrokinase-type plasminogen activatorHomo sapiens (human)
protein complex involved in cell-matrix adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
serine-type endopeptidase complexUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular spaceUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1312519Antiproliferative activity against human PC3 cells assessed as cell viability at 20 uM after 72 hrs by WST-1 assay relative to control2016European journal of medicinal chemistry, Aug-08, Volume: 118Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.
AID490791Antioxidant activity assessed as inhibition of pyrogallol autooxidation2010European journal of medicinal chemistry, Jul, Volume: 45, Issue:7
1,2-ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action.
AID213433Acid dissociation constant (pKa) of the compound2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Identification of novel inhibitors of urokinase via NMR-based screening.
AID1312516Antiproliferative activity against human bone marrow cells after 72 hrs by WST-1 assay2016European journal of medicinal chemistry, Aug-08, Volume: 118Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.
AID402798Inhibition of amidolytic activity of human recombinant soluble tissue factor/human factor 7a preincubated with factor 7a for 90 mins1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID402797Inhibition of amidolytic activity of human recombinant soluble tissue factor/human factor 7a preincubated with factor 7a for 15 mins1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID1312517Antiproliferative activity against human MCR5A cells after 72 hrs by WST-1 assay2016European journal of medicinal chemistry, Aug-08, Volume: 118Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.
AID1312518Antiproliferative activity against human OVCAR3 cells assessed as cell viability at 20 uM after 72 hrs by WST-1 assay relative to control2016European journal of medicinal chemistry, Aug-08, Volume: 118Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.
AID1312520Antiproliferative activity against human MDA-MB-231 cells assessed as cell viability at 20 uM after 72 hrs by WST-1 assay relative to control2016European journal of medicinal chemistry, Aug-08, Volume: 118Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.
AID215985Inhibitory activity against Urokinase-type plasminogen activator2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Identification of novel inhibitors of urokinase via NMR-based screening.
AID402796Inhibition of amidolytic activity of human recombinant soluble tissue factor (Ala-TF 1 to 219)/human factor 7a1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID402799Inhibition of amidolytic activity of human recombinant soluble tissue factor/human factor 7a preincubated with tissue factor for 15 mins1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID1252829Inhibition of Dengue virus (serotype 2) NS2B-NS3 protease at 100 uM preincubated with protein for 15 mins followed by substrate addition measured after 15 mins by spectrofluorometric analysis2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Phenylalanine and Phenylglycine Analogues as Arginine Mimetics in Dengue Protease Inhibitors.
AID402800Inhibition of amidolytic activity of human recombinant soluble tissue factor/human factor 7a preincubated with tissue factor for 90 mins1998Journal of natural products, Nov, Volume: 61, Issue:11
Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
AID239526In vitro inhibitory activity towards Coagulation factor X was determined using chromogenic substrate, MeO-COD-CHG-Gly-Arg-pNA2004Bioorganic & medicinal chemistry letters, Oct-18, Volume: 14, Issue:20
Design, synthesis, and evaluation of oxyanion-hole selective inhibitor substituents for the S1 subsite of factor Xa.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (102)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (27.45)18.7374
1990's29 (28.43)18.2507
2000's18 (17.65)29.6817
2010's20 (19.61)24.3611
2020's7 (6.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.62

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 Index24.62 (24.57)
Research Supply Index4.65 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index23.70 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.96%)6.00%
Case Studies2 (1.92%)4.05%
Observational0 (0.00%)0.25%
Other101 (97.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]