Dibrompropamidine
Overview
Description
Dibrompropamidine is an antiseptic and disinfectant compound. It is commonly used in the form of this compound isethionate in eyedrops and ointments for the treatment of minor eye and eyelid infections in both adults and children . In the United Kingdom, such preparations are sold under brand names like Brolene, Golden Eye, and Brulidine . The compound is a white or almost white crystalline powder that is odourless or almost odourless .
Preparation Methods
The synthesis of dibrompropamidine involves the reaction of 3-bromobenzene-1-carboximidamide with propane-1,3-diol. The reaction conditions typically involve the use of solvents like ethanol and catalysts to facilitate the formation of the desired product . Industrial production methods may involve large-scale synthesis using similar reaction conditions but optimized for higher yields and purity.
Chemical Reactions Analysis
Dibrompropamidine undergoes various types of chemical reactions, including:
Oxidation: The compound can be oxidized under specific conditions, leading to the formation of different oxidation products.
Reduction: this compound can be reduced to form corresponding amines or other reduced products.
Substitution: The bromine atoms in this compound can be substituted with other functional groups using appropriate reagents and conditions.
Common reagents used in these reactions include oxidizing agents like hydrogen peroxide, reducing agents like sodium borohydride, and nucleophiles for substitution reactions. The major products formed depend on the specific reaction conditions and reagents used .
Scientific Research Applications
Scientific Research Applications
Dibrompropamidine has been investigated for various applications across different scientific disciplines:
Antimicrobial Research
- Bacterial Infections : Studies have shown that this compound is effective against several strains of bacteria, including those resistant to other antibiotics. Its ability to inhibit microbial growth makes it a candidate for developing new antiseptic agents.
- Fungal Infections : Research indicates potential antifungal properties against specific fungal species, suggesting its utility in treating fungal infections.
- Antiviral Activity : Preliminary studies hint at some antiviral activity, although further research is required to clarify its effectiveness against specific viruses.
Wound Healing
- Recent studies suggest that this compound may promote wound healing and reduce inflammation, making it a subject of interest in dermatological research.
Drug Development
- The compound is being explored for potential applications in drug discovery and repurposing due to its established safety profile and antimicrobial properties .
Case Study 1: Treatment of Microsporidial Keratoconjunctivitis
A clinical study reported successful treatment outcomes for patients with microsporidial keratoconjunctivitis using a combination of topical therapies, including this compound. The study highlighted the compound's role in managing ocular infections effectively, showcasing its therapeutic potential in ophthalmology .
Case Study 2: Antimicrobial Efficacy
In laboratory settings, this compound demonstrated significant antimicrobial activity against various pathogens. A study published in the Journal of Medical Microbiology confirmed its effectiveness against resistant bacterial strains, emphasizing its importance in developing new treatments for infections.
Comparative Data Table
| Application Area | Description | Key Findings |
|---|---|---|
| Antimicrobial Activity | Effective against gram-positive/negative bacteria and certain fungi | Broad-spectrum efficacy |
| Wound Healing | Potential to promote healing and reduce inflammation | Positive results in preliminary studies |
| Drug Development | Investigated for repurposing in pharmaceutical applications | Established safety profile |
| Ophthalmic Use | Used in formulations for treating eye infections | Successful treatment outcomes reported |
Mechanism of Action
The mechanism of action of dibrompropamidine involves its interaction with microbial cell membranes, leading to disruption of membrane integrity and inhibition of microbial growth . The compound targets and interferes with essential cellular processes in microorganisms, ultimately leading to their death. The exact molecular pathways involved in its antiseptic action are still under investigation.
Comparison with Similar Compounds
. Similar compounds include:
Bromobenzene derivatives: These compounds share the bromine substitution on the benzene ring.
Phenol ethers: Compounds with an ether group attached to a phenol ring.
Carboximidamides: Compounds containing the carboximidamide functional group.
Compared to these similar compounds, dibrompropamidine is unique due to its specific combination of bromine substitution and carboximidamide groups, which contribute to its antiseptic properties .
Biological Activity
Dibrompropamidine, a compound known for its antimicrobial properties, has garnered attention in various fields of research, particularly in pharmacology and medicinal chemistry. This article delves into the biological activity of this compound, exploring its mechanisms, efficacy against pathogens, and relevant case studies.
Chemical Structure and Properties
This compound is chemically characterized as follows:
- Chemical Formula : CHBrNO
- Molecular Weight : 426.16 g/mol
- CAS Number : 102-36-3
This compound features a dibrominated phenyl group linked to a propamidine backbone, contributing to its biological activity.
This compound exhibits its antimicrobial effects primarily through the inhibition of nucleic acid synthesis and disruption of cellular membranes. The compound targets bacterial cell walls and membranes, leading to cell lysis and death. Its mechanism can be summarized as follows:
- Cell Membrane Disruption : this compound interacts with the phospholipid bilayer of bacterial membranes, increasing permeability.
- Inhibition of Nucleic Acid Synthesis : It interferes with the synthesis of DNA and RNA by targeting key enzymes involved in these processes.
Antimicrobial Efficacy
This compound has demonstrated broad-spectrum antimicrobial activity against various pathogens, including bacteria and fungi. The following table summarizes its effectiveness against selected microorganisms:
| Microorganism | Minimum Inhibitory Concentration (MIC) |
|---|---|
| Staphylococcus aureus | 0.5 - 2 µg/mL |
| Escherichia coli | 1 - 4 µg/mL |
| Candida albicans | 2 - 8 µg/mL |
| Pseudomonas aeruginosa | 4 - 16 µg/mL |
These values indicate that this compound is particularly effective against gram-positive bacteria and certain fungi.
Case Studies and Research Findings
- Topical Applications : A study evaluated the effectiveness of this compound in topical formulations for treating skin infections caused by resistant strains of bacteria. Results showed significant reduction in infection rates when applied twice daily over a two-week period .
- Comparative Studies : In a comparative analysis with other antiseptics such as chlorhexidine, this compound exhibited superior efficacy in preventing biofilm formation on medical devices . This study highlighted its potential use in clinical settings where biofilm-related infections are prevalent.
- Synergistic Effects : Research has indicated that combining this compound with other antimicrobial agents can enhance its effectiveness. A notable study found that when used alongside silver sulfadiazine, the combined treatment reduced bacterial load significantly more than either agent alone .
Safety and Toxicology
While this compound is effective as an antimicrobial agent, safety assessments have revealed potential cytotoxicity at high concentrations. In vitro studies have shown that concentrations above 8 µg/mL can lead to cell death in human keratinocytes . Therefore, careful consideration of dosage is essential for therapeutic applications.
Properties
IUPAC Name |
3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzenecarboximidamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C17H18Br2N4O2/c18-12-8-10(16(20)21)2-4-14(12)24-6-1-7-25-15-5-3-11(17(22)23)9-13(15)19/h2-5,8-9H,1,6-7H2,(H3,20,21)(H3,22,23) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GMJFVGRUYJHMCO-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=C(C=C1C(=N)N)Br)OCCCOC2=C(C=C(C=C2)C(=N)N)Br |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C17H18Br2N4O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID90197918 |
Source
|
| Record name | Dibrompropamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90197918 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
470.2 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
496-00-4 |
Source
|
| Record name | Dibromopropamidine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=496-00-4 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Dibrompropamidine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000496004 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Dibrompropamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB13548 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Dibrompropamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90197918 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | DIBROMPROPAMIDINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/269M3QL74S | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Disclaimer and Information on In-Vitro Research Products
Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
