Page last updated: 2024-12-05

dibrompropamidine

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

Dibrompropamidine is a synthetic, broad-spectrum antimicrobial agent that is effective against a wide range of bacteria, fungi, and parasites. It is a derivative of propamidine, a compound that was originally developed as an anti-trypanosomal drug. Dibrompropamidine is synthesized through a series of chemical reactions, typically starting with the halogenation of propamidine with bromine. The compound is known for its potent activity against trypanosomes, leishmania, and other protozoan parasites, making it a valuable tool for the treatment of diseases such as African trypanosomiasis and leishmaniasis. Dibrompropamidine is also effective against a variety of bacterial and fungal infections, including infections caused by Staphylococcus aureus, Candida albicans, and Cryptococcus neoformans. It is currently used in veterinary medicine to treat various infections in animals. Research into dibrompropamidine continues to explore its potential therapeutic applications, including its potential as an anti-cancer agent and its ability to inhibit viral replication. Studies are also being conducted to develop new synthetic analogs of dibrompropamidine with improved pharmacological properties.'

Cross-References

ID SourceID
PubMed CID11974
CHEMBL ID30044
CHEBI ID135760
SCHEMBL ID292947
MeSH IDM0151760

Synonyms (30)

Synonym
D07204
dibrompropamidine (inn)
496-00-4
dibrompropamidine
CHEBI:135760
dibromopropamidine
CHEMBL30044 ,
3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzenecarboximidamide
4-(3-{4-[amino(imino)methyl]-2-bromophenoxy}propoxy)-3-bromobenzenecarboximidamide
bdbm50098554
NCGC00189076-01
dibrompropamidinum
dibromopropamidina
unii-269m3ql74s
269m3ql74s ,
dibromopropamidina [inn-spanish]
4,4'-(trimethylenedioxy)bis(3-bromobenzamidine)
dibrompropamidine [inn:ban]
dibrompropamidinum [inn-latin]
SCHEMBL292947
dibrompropamidine [who-dd]
dibromopropamidine [mi]
dibrompropamidine [inn]
dibrompropamidin
DTXSID90197918
3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzene-1-carboximidamide
Q5272294
benzenecarboximidamide, 4,4'-[1,3-propanediylbis(oxy)]bis[3-bromo-
DB13548
GMJFVGRUYJHMCO-UHFFFAOYSA-N
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency18.10560.007215.758889.3584AID624030
[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)
ProthrombinHomo sapiens (human)Ki0.94600.00000.78469.0000AID211360
Urokinase-type plasminogen activatorHomo sapiens (human)Ki1.57000.01702.62687.0000AID228651
AcrosinSus scrofa (pig)Ki1.70001.70002.87504.0000AID1133059
Suppressor of tumorigenicity 14 proteinHomo sapiens (human)Ki0.53500.00000.87113.3500AID108587
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (54)

Processvia Protein(s)Taxonomy
positive regulation of protein phosphorylationProthrombinHomo sapiens (human)
proteolysisProthrombinHomo sapiens (human)
acute-phase responseProthrombinHomo sapiens (human)
cell surface receptor signaling pathwayProthrombinHomo sapiens (human)
G protein-coupled receptor signaling pathwayProthrombinHomo sapiens (human)
blood coagulationProthrombinHomo sapiens (human)
positive regulation of cell population proliferationProthrombinHomo sapiens (human)
regulation of cell shapeProthrombinHomo sapiens (human)
response to woundingProthrombinHomo sapiens (human)
negative regulation of platelet activationProthrombinHomo sapiens (human)
platelet activationProthrombinHomo sapiens (human)
regulation of blood coagulationProthrombinHomo sapiens (human)
positive regulation of blood coagulationProthrombinHomo sapiens (human)
positive regulation of cell growthProthrombinHomo sapiens (human)
positive regulation of insulin secretionProthrombinHomo sapiens (human)
positive regulation of collagen biosynthetic processProthrombinHomo sapiens (human)
fibrinolysisProthrombinHomo sapiens (human)
negative regulation of proteolysisProthrombinHomo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STATProthrombinHomo sapiens (human)
negative regulation of astrocyte differentiationProthrombinHomo sapiens (human)
positive regulation of release of sequestered calcium ion into cytosolProthrombinHomo sapiens (human)
regulation of cytosolic calcium ion concentrationProthrombinHomo sapiens (human)
cytolysis by host of symbiont cellsProthrombinHomo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionProthrombinHomo sapiens (human)
negative regulation of fibrinolysisProthrombinHomo sapiens (human)
antimicrobial humoral immune response mediated by antimicrobial peptideProthrombinHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumProthrombinHomo sapiens (human)
positive regulation of lipid kinase activityProthrombinHomo sapiens (human)
negative regulation of cytokine production involved in inflammatory responseProthrombinHomo sapiens (human)
positive regulation of protein localization to nucleusProthrombinHomo sapiens (human)
positive regulation of phospholipase C-activating G protein-coupled receptor signaling pathwayProthrombinHomo sapiens (human)
ligand-gated ion channel signaling pathwayProthrombinHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processProthrombinHomo sapiens (human)
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)
neural tube closureSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
proteolysisSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
protein catabolic processSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
keratinocyte differentiationSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
epithelial cell morphogenesis involved in placental branchingSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
lipopolysaccharide bindingProthrombinHomo sapiens (human)
serine-type endopeptidase activityProthrombinHomo sapiens (human)
signaling receptor bindingProthrombinHomo sapiens (human)
calcium ion bindingProthrombinHomo sapiens (human)
protein bindingProthrombinHomo sapiens (human)
growth factor activityProthrombinHomo sapiens (human)
heparin bindingProthrombinHomo sapiens (human)
thrombospondin receptor activityProthrombinHomo sapiens (human)
serine-type endopeptidase activityUrokinase-type plasminogen activatorHomo sapiens (human)
protein bindingUrokinase-type plasminogen activatorHomo sapiens (human)
serine-type endopeptidase activitySuppressor of tumorigenicity 14 proteinHomo sapiens (human)
serine-type peptidase activitySuppressor of tumorigenicity 14 proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
external side of plasma membraneProthrombinHomo sapiens (human)
collagen-containing extracellular matrixProthrombinHomo sapiens (human)
extracellular regionProthrombinHomo sapiens (human)
extracellular spaceProthrombinHomo sapiens (human)
endoplasmic reticulum lumenProthrombinHomo sapiens (human)
Golgi lumenProthrombinHomo sapiens (human)
plasma membraneProthrombinHomo sapiens (human)
extracellular exosomeProthrombinHomo sapiens (human)
blood microparticleProthrombinHomo sapiens (human)
collagen-containing extracellular matrixProthrombinHomo sapiens (human)
extracellular spaceProthrombinHomo sapiens (human)
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)
extracellular spaceSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
plasma membraneSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
external side of plasma membraneSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
basolateral plasma membraneSuppressor of tumorigenicity 14 proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID108587compound was tested for inhibitory activity against Matriptase2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase.
AID1133059Reversible competitive inhibition of boar spermatozoa acrosin using BzArgOEt as substrate by Dixon plot analysis1978Journal of medicinal chemistry, Nov, Volume: 21, Issue:11
Structure-activity relationships for the inhibition of acrosin by benzamidine derivatives.
AID228651compound was tested for inhibitory activity against Urokinase-type plasminogen activator (microPa)2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase.
AID211360compound was tested for inhibitory activity against Thrombin2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (45.45)18.7374
1990's8 (24.24)18.2507
2000's9 (27.27)29.6817
2010's1 (3.03)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.46

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 Index24.46 (24.57)
Research Supply Index3.56 (2.92)
Research Growth Index4.11 (4.65)
Search Engine Demand Index50.43 (26.88)
Search Engine Supply Index4.00 (0.95)

This Compound (24.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies12 (35.29%)4.05%
Observational0 (0.00%)0.25%
Other22 (64.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Randomized, Active-Controlled, Phase 3 Study to Evaluate Efficacy, Safety and Tolerability of 0.08% PHMB Ophthalmic Solution in Comparison With 0.02% PHMB + 0.1% Propamidine Combination Therapy in Subjects Affected by Acanthamoeba Keratitis [NCT03274895]Phase 3135 participants (Actual)Interventional2017-08-13Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT03274895 (3) [back to overview]Clinical Resolution Rate
NCT03274895 (3) [back to overview]Time to Cure
NCT03274895 (3) [back to overview]Visual Acuity

Clinical Resolution Rate

Percentage of patients cured 30 days after discontinuing all study therapies, within 12 months of randomization (NCT03274895)
Timeframe: 12 months

Interventionpercentage of participants (Number)
PHMB 0.08% Plus Placebo84.8
PHMB 0.02% Plus Propamidine 0.1%88.5

[back to top]

Time to Cure

Time needed to reach a clinical resolution (NCT03274895)
Timeframe: maximum 12 months

Interventiondays (Median)
PHMB 0.08% Plus Placebo140
PHMB 0.02% Plus Propamidine 0.1%114

[back to top]

Visual Acuity

Final visual acuity (best corrected) (NCT03274895)
Timeframe: maximum 12 months

InterventionLogMAR (Median)
PHMB 0.08% Plus Placebo0.000
PHMB 0.02% Plus Propamidine 0.1%0.000

[back to top]