Diloxanid
Übersicht
Beschreibung
Diloxanide is a medication primarily used to treat infections caused by protozoa, specifically amoebas. It is commonly used to manage and eliminate Entamoeba histolytica infections, which can cause amoebic dysentery and other gastrointestinal problems .
Wissenschaftliche Forschungsanwendungen
Introduction to Diloxanide
Diloxanide, particularly in its furoate form, is an anti-protozoal medication primarily employed in the treatment of infections caused by Entamoeba histolytica, which leads to amoebiasis. This compound is notable for its efficacy in treating asymptomatic intestinal amebiasis and can be used in conjunction with other anti-amebic agents for more severe cases.
Treatment of Amoebiasis
Diloxanide is primarily indicated for the treatment of asymptomatic intestinal amebiasis, where it serves as a first-line agent. It can also be used alongside nitroimidazoles (e.g., metronidazole) for invasive forms of the disease, showcasing its versatility in addressing varying severities of E. histolytica infections .
Alternative Therapies
Recent research has explored the potential of diloxanide furoate in alternative therapies, particularly against Cryptosporidium parvum, a protozoan that causes gastrointestinal illness. Studies have focused on developing bioadhesive formulations that incorporate diloxanide furoate to enhance drug delivery and efficacy against this pathogen .
Analytical Methods
There has been significant progress in developing analytical methods for the simultaneous determination of diloxanide furoate and other compounds. Techniques such as high-performance liquid chromatography (HPLC) have been validated for their accuracy and reliability in detecting diloxanide furoate alongside other anti-amebic agents like metronidazole and spiramycin .
Case Study 1: Efficacy Against Entamoeba histolytica
A clinical study evaluated the effectiveness of diloxanide furoate in patients diagnosed with asymptomatic intestinal amebiasis. Results indicated high rates of cyst clearance and symptomatic resolution when administered as a standalone treatment or in combination with metronidazole. The study highlighted the importance of using diloxanide as a primary treatment option due to its favorable safety profile and effectiveness .
Case Study 2: Formulation Development
In another research effort, scientists developed a particulate drug formulation utilizing diloxanide furoate aimed at improving treatment outcomes for cryptosporidiosis. The formulation involved encapsulating the drug within microspheres made from chitosan and poly(vinyl alcohol), which demonstrated enhanced bioavailability and therapeutic efficacy in preclinical models .
Data Tables
| Study Focus | Treatment Regimen | Outcome |
|---|---|---|
| Asymptomatic Amoebiasis | Diloxanide furoate alone | High cyst clearance rate |
| Severe Amoebiasis | Diloxanide + Metronidazole | Improved symptom resolution |
| Cryptosporidiosis | Bioadhesive formulation | Enhanced drug delivery |
Wirkmechanismus
Target of Action
Diloxanide primarily targets the protozoan parasite Entamoeba histolytica . This parasite is responsible for causing amoebiasis, a type of gastrointestinal infection. The drug acts as a luminal amebicide, meaning it works within the intestines to eliminate the parasite .
Mode of Action
histolytica, which are the active, feeding stage of the parasite . It is also suggested that Diloxanide may inhibit protein synthesis .
Biochemical Pathways
Diloxanide’s action leads to the destruction of E. histolytica trophozoites, which eventually form into cysts . These cysts are then excreted by individuals infected with asymptomatic amoebiasis
Pharmacokinetics
Diloxanide furoate, the prodrug form of Diloxanide, is hydrolyzed in the gastrointestinal tract to produce the active drug . The bioavailability of Diloxanide is approximately 90% . After absorption, Diloxanide is extensively metabolized, primarily through glucuronidation . About 90% of the drug is rapidly excreted in the urine as a glucuronide metabolite, and the remaining 10% is excreted in the feces as Diloxanide . The half-life of Diloxanide is approximately 3 hours .
Result of Action
The primary result of Diloxanide’s action is the elimination of E. histolytica from the intestines of infected individuals . By destroying the trophozoites and preventing the formation of new cysts, Diloxanide helps to stop the spread of the infection .
Action Environment
Diloxanide is effective in the environment of the human gastrointestinal tract, where E. histolytica resides . The drug is designed to withstand the conditions of this environment, ensuring its stability and efficacy.
Biochemische Analyse
Biochemical Properties
Diloxanide is a luminal amebicide, meaning it destroys the trophozoites of E. histolytica that eventually form into cysts .
Cellular Effects
Diloxanide exerts its effects primarily on the cells of the protozoa E. histolytica. It destroys the trophozoites of this organism, which are the active, feeding stage of the life cycle . The destruction of these cells prevents the formation of cysts, which are the dormant stage that allows the protozoa to survive outside the host .
Molecular Mechanism
It is thought that diloxanide may inhibit protein synthesis . This would interfere with the growth and reproduction of the protozoa, leading to their destruction .
Temporal Effects in Laboratory Settings
The effects of diloxanide have been studied extensively in laboratory settings. Diloxanide is a prodrug, and is hydrolyzed in the gastrointestinal tract to produce the active ingredient . It has a half-life of about 3 hours .
Dosage Effects in Animal Models
The effects of diloxanide in animal models have not been extensively studied. It is known that diloxanide is used in the treatment of asymptomatic (cyst passers) intestinal amebiasis caused by Entamoeba histolytica .
Metabolic Pathways
Diloxanide is metabolized in the body by hydrolysis to furoic acid and diloxanide. The diloxanide is then extensively glucuronidated, with 99% of diloxanide occurring as glucuronide and 1% as free diloxanide in the systemic circulation .
Transport and Distribution
Diloxanide is slowly absorbed from the gastrointestinal tract . It is then distributed throughout the body, where it exerts its effects on the cells of the protozoa E. histolytica .
Subcellular Localization
The subcellular localization of diloxanide is not well understood. As a luminal amebicide, it is likely that it exerts its effects primarily in the lumen of the intestine, where the protozoa E. histolytica reside .
Vorbereitungsmethoden
Synthesewege und Reaktionsbedingungen: Diloxanid kann durch einen mehrstufigen Prozess synthetisiert werden, der die Reaktion von 4-Chloranilin mit Dichloracetylchlorid zur Bildung von Dichloracetyl-4-chloranilin umfasst. Dieser Zwischenstoff wird dann mit Furan-2-carbonsäure umgesetzt, um this compound zu erhalten .
Industrielle Produktionsmethoden: Die industrielle Produktion von this compound erfolgt in der Regel im großen Maßstab unter Verwendung der gleichen chemischen Grundreaktionen, die jedoch zur Steigerung der Effizienz und Ausbeute optimiert wurden. Dies beinhaltet die präzise Steuerung von Reaktionsbedingungen wie Temperatur, Druck und pH-Wert, um eine hohe Reinheit und Konsistenz des Endprodukts zu gewährleisten .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Diloxanid unterliegt verschiedenen Arten von chemischen Reaktionen, darunter:
Hydrolyse: Diloxanidfuroat wird im Magen-Darm-Trakt hydrolysiert, um this compound und Furoinsäure zu bilden.
Glucuronidierung: this compound unterliegt einer ausgedehnten Glucuronidierung in der Leber, wobei Glucuronidkonjugate gebildet werden, die im Urin ausgeschieden werden.
Häufige Reagenzien und Bedingungen:
Hydrolyse: Findet typischerweise unter sauren oder basischen Bedingungen in Gegenwart von Wasser statt.
Glucuronidierung: Katalysiert durch Enzyme in der Leber unter physiologischen Bedingungen.
Hauptprodukte, die gebildet werden:
Hydrolyse: Bildet this compound und Furoinsäure.
Glucuronidierung: Bildet Diloxanidglucuronid.
Vergleich Mit ähnlichen Verbindungen
Paromomycin: Another luminal amebicide used to treat amoebic infections.
Metronidazole: Used to treat symptomatic amoebic infections and can penetrate tissues, unlike diloxanide.
Tinidazole: Similar to metronidazole, used for treating symptomatic amoebic infections.
Comparison:
Diloxanide vs. Paromomycin: Diloxanide is often used as a second-line treatment when paromomycin is not available or suitable.
Diloxanide vs. Metronidazole/Tinidazole: Diloxanide is used after treatment with metronidazole or tinidazole for symptomatic infections.
Diloxanide’s unique role as a luminal amebicide makes it a valuable tool in the treatment of amoebic infections, particularly in cases where other treatments are not suitable or available.
Biologische Aktivität
Diloxanide, particularly in its furoate form, is an anti-protozoal medication primarily used to treat asymptomatic intestinal amebiasis caused by Entamoeba histolytica. Its efficacy and biological activity have been the subject of various studies, revealing critical insights into its pharmacodynamics, mechanisms of action, and clinical applications.
The exact mechanism of action of diloxanide remains largely unknown; however, it is believed to act as a luminal amebicide , effectively destroying the trophozoites of E. histolytica that can develop into cysts. This action prevents the excretion of cysts by asymptomatic carriers, thereby controlling the spread of the infection . Some studies suggest that diloxanide may inhibit protein synthesis in E. histolytica, which contributes to its anti-amebic effects .
Pharmacokinetics
- Bioavailability : Diloxanide has a bioavailability of approximately 90% when administered in its parent form. In contrast, diloxanide furoate is slowly absorbed from the gastrointestinal tract, ensuring prolonged luminal concentration .
- Metabolism : Diloxanide furoate is hydrolyzed into diloxanide and furoic acid in the intestinal lumen before absorption. The absorbed diloxanide undergoes extensive glucuronidation, with 99% existing as glucuronide in systemic circulation .
Clinical Efficacy
Diloxanide has demonstrated high efficacy rates in clinical settings:
- In a study involving 54 patients treated with a combination of diloxanide furoate and metronidazole, parasitic clearance was achieved in 100% of cases .
- Another study reported an efficacy rate of 93% for patients treated with diloxanide furoate among those who previously failed treatment with metronidazole or tinidazole .
Efficacy in Asymptomatic Patients
A significant body of research highlights the effectiveness of diloxanide furoate in treating asymptomatic carriers:
- A randomized controlled trial showed that among patients treated with diloxanide furoate, the parasitological cure rate was significantly higher (93%) compared to metronidazole (29%-56%) in previous studies .
- In a broader analysis involving 575 treatment courses for asymptomatic individuals passing cysts, an 86% cure rate was observed following a full treatment course .
Cost-Effectiveness Analysis
A cost-effectiveness analysis indicated that combining metronidazole with diloxanide results in improved treatment outcomes at a slightly higher cost. The incremental cost-effectiveness ratio (ICER) was calculated at $8 per amoebic case cured when comparing this combination to metronidazole alone .
Efficacy Comparison Table
| Treatment Regimen | Cure Rate (%) |
|---|---|
| Metronidazole Alone | 29 - 56 |
| Metronidazole + Diloxanide | 100 |
| Diloxanide Alone | 93 |
| Overall Cure Rate (asymptomatic cases) | 86 |
Pharmacokinetic Profile Table
| Parameter | Diloxanide | Diloxanide Furoate |
|---|---|---|
| Bioavailability | ~90% | Slow absorption |
| Metabolism | Glucuronidation | Hydrolyzed to active form |
| Route of Elimination | Not specified | Not specified |
Eigenschaften
IUPAC Name |
2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C9H9Cl2NO2/c1-12(9(14)8(10)11)6-2-4-7(13)5-3-6/h2-5,8,13H,1H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GZZZSOOGQLOEOB-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN(C1=CC=C(C=C1)O)C(=O)C(Cl)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C9H9Cl2NO2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0022939 |
Source
|
| Record name | Diloxanide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0022939 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
234.08 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Mechanism of Action |
Unknown. Diloxanide may inhibit protein synthesis. |
Source
|
| Record name | Diloxanide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08792 | |
| 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) | |
CAS No. |
579-38-4 |
Source
|
| Record name | Diloxanide | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=579-38-4 | |
| 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 | Diloxanide [INN:BAN:DCF] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000579384 | |
| 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 | Diloxanide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08792 | |
| 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 | Diloxanide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0022939 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Diloxanide | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.008.583 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | DILOXANIDE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/89134SCM7M | |
| 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
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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
Q1: How does Diloxanide furoate exert its effects within the body?
A1: While the precise mechanism of action remains not fully elucidated, research suggests Diloxanide furoate primarily targets the lumen of the intestine, exerting its effects directly on luminal amoebae. [] It is considered a luminal amoebicide, primarily active against Entamoeba histolytica trophozoites residing within the gut. [, ] This targeted action makes it particularly effective for treating asymptomatic intestinal amoebiasis. [, ]
Q2: What is the molecular formula and weight of Diloxanide furoate?
A2: Diloxanide furoate has the molecular formula C14H11Cl2NO4 and a molecular weight of 328.15 g/mol. []
Q3: Are there any spectroscopic data available for Diloxanide furoate?
A3: Yes, several studies employ spectroscopic techniques for analysis:
- PMR Spectroscopy: A PMR spectroscopy method using tetramethylsilane (TMS) as an internal standard was developed to quantify Diloxanide furoate in both pure powder and tablet formulations. The method relies on the N-CH3 protons singlet peak at δ = 3.23 for quantitative measurement. []
- UV Spectrophotometry: UV spectrophotometry plays a crucial role in analyzing Diloxanide furoate. Studies use specific wavelengths for detection and quantification, including 258 nm, 270 nm, 280 nm, and 311 nm, depending on the analytical method and the other compounds present in the sample. [, , , , , ]
Q4: How does the presence of carbohydrates affect the stability of Diloxanide furoate?
A4: Research indicates that certain carbohydrates can influence Diloxanide furoate stability. In alkaline conditions, sucrose, glucose, fructose, and lactose were found to accelerate the hydrolysis of Diloxanide furoate at 40°C. [] Interestingly, Diloxanide furoate exhibited better stability in fructose, lactose, and sorbitol solutions at room temperature. []
Q5: How does light exposure impact the stability of Diloxanide furoate?
A5: Studies reveal Diloxanide furoate is susceptible to photodegradation. Exposure to UV irradiation, artificial room light, and sunlight leads to degradation. The photodegradation process follows first-order kinetics in both quartz cells and glass bottles. Solvent choice also influences the rate of photodegradation. []
Q6: What strategies can enhance Diloxanide furoate's photostability?
A6: The addition of photoprotective agents like para-aminobenzoic acid (PABA) and ascorbic acid significantly improves the photostability of Diloxanide furoate solutions exposed to 254 nm UV irradiation. Commercially available Tang® preparation, containing sugars, buffers, stabilizers, and artificial colors, also demonstrated a photoprotective effect. []
Q7: What formulation strategies are explored to enhance Diloxanide furoate's delivery and performance?
A7: Several approaches are under investigation to optimize Diloxanide furoate delivery:
- Cyclodextrin Complexation: Complexation with β-cyclodextrin (βCD), methyl-β-cyclodextrin (MβCD), and hydroxypropyl-β-cyclodextrin (HPβCD) has been shown to significantly improve the solubility and dissolution rate of Diloxanide furoate. [] This strategy holds promise for enhancing its bioavailability and therapeutic efficacy.
- pH-Dependent Polymers: Studies explore colon-targeted delivery using pH-sensitive polymers like Eudragit S100, Eudragit L 100, and Cellulose acetate phthallate. These polymers aim to control drug release in specific intestinal regions for optimal therapeutic effect. []
Q8: What analytical techniques are commonly employed in Diloxanide furoate research?
A8: A range of analytical techniques are utilized to characterize and quantify Diloxanide furoate:
- High-Performance Liquid Chromatography (HPLC): This versatile technique is frequently used to assay Diloxanide furoate in pharmaceutical formulations, study its stability, and analyze its presence in biological samples. Different variations of HPLC, including RP-HPLC, are employed. [, , , , , , , , , , , , , ]
- Thin-Layer Chromatography (TLC): This method provides a rapid and cost-effective way to separate and quantify Diloxanide furoate in mixtures. High-performance TLC (HPTLC) offers enhanced sensitivity and resolution for analysis. [, ]
- UV Spectrophotometry: This technique utilizes the absorption properties of Diloxanide furoate at specific wavelengths to determine its concentration in various samples. [, , , ]
- Difference Spectrophotometry: This technique measures the absorbance difference at specific wavelengths, allowing the determination of Diloxanide furoate in the presence of other components. []
Q9: How is the validity of these analytical methods ensured?
A9: The analytical methods employed in Diloxanide furoate research undergo rigorous validation procedures following guidelines set by organizations like the International Conference on Harmonisation (ICH). [, , , , , , , ] The validation process typically involves assessing parameters like linearity, accuracy, precision, specificity, limit of detection (LOD), and limit of quantitation (LOQ). [, , , , , , ] This rigorous validation process ensures the reliability and reproducibility of the results obtained from these analytical methods.
Q10: What is the clinical significance of distinguishing pathogenic from non-pathogenic Entamoeba histolytica strains?
A10: The identification of distinct pathogenic and non-pathogenic Entamoeba histolytica strains has important implications for treatment decisions. While both strains can colonize the human gut, only pathogenic strains cause invasive disease. [] Therefore, treatment with Diloxanide furoate, a luminal amebicide, is typically recommended only for infections confirmed to be caused by pathogenic strains. [, , ]
Q11: What challenges are associated with treating intestinal amoebiasis in specific populations?
A11: Difficulties in treatment can arise in settings where hygiene and sanitation are compromised, potentially leading to reinfection. This has been observed in institutions housing mentally disabled individuals. In such cases, combined therapeutic approaches, including metronidazole followed by Diloxanide furoate, have proven effective in controlling the spread of infection. []
Q12: How does Diloxanide furoate compare to other available treatments for amoebiasis?
A12: While Diloxanide furoate effectively targets luminal amoebae, it might not be sufficient to completely eliminate amoebae residing within tissues. [, , , ] In such cases, a combination therapy approach, often involving metronidazole or other nitroimidazole derivatives followed by Diloxanide furoate, is recommended. [, , , ] The choice of treatment often depends on the clinical presentation, the severity of infection, and the presence or absence of extraintestinal involvement.
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