Fenbendazole: Chemical Properties and Applications
Fenbendazole, a benzimidazole â˘anthelminticâ compound,â has âgarnered⣠attention â˘in â˘both veterinary and âŁmedical⣠fields due to its⣠diverse applications. This articleâ explores⣠the chemical properties of fenbendazole, including its molecular structure,⢠solubility, âand stability, as wellâ as its various usesâ in animal health and potential human applications. Byâ examiningâ the compound’s â˘characteristics and effectivenessâ against parasitic infections, we aim to â˘provide a thorough overview of⤠fenbendazole’s role⤠in modern medicine and⣠parasitology.
Table of Contents
- Chemical Structure and Composition of Fenbendazole
- Physicochemical Properties and Stabilityâ of Fenbendazole
- Mechanism of Action and⤠Pharmacokinetics
- Veterinary Applicationsâ and âDosage â˘Recommendations
- Potential âŁHuman Uses and Clinical âTrials
- Safety⢠Profile and â¤Environmental Impact âof Fenbendazole
- Q&A
- Insights and Conclusions
Chemical â¤structure and⣠Composition âof Fenbendazole
Fenbendazole is a âbenzimidazole compound âwith the⣠molecular formula C15H13N3O2S. Its systematic name is methyl N-[6-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate. The molecule consists⢠of â¤a benzimidazoleâ core âwith a phenylthio âgroup attached at the 6-position and a methyl carbamate group at the 2-position. This unique structural⣠arrangementâ contributesâ to its⣠anthelmintic âŁproperties â and its ability â˘to âdisrupt microtubule âŁformation in parasites.
Theâ chemical composition of⢠fenbendazole includes:
- Carbon (62.27%)
- hydrogen⣠(4.53%)
- Nitrogen (14.53%)
- Oxygen (11.07%)
- Sulfur (11.08%)
Its molecular weight is 299.35 âg/mol, and it appears as a⤠whiteâ to off-white crystalline solid. â˘Fenbendazole exhibits low solubility in water but is âsoluble⤠in organic⤠solvents such as dimethylâ sulfoxide (DMSO) and dimethylformamide (DMF). thisâ lipophilic nature allows it to easily penetrate cell membranes and âreach its target sitesâ within parasitic organisms.
Physicochemical Properties and stability of â¤Fenbendazole
Fenbendazole, a benzimidazole anthelmintic, exhibits distinct âphysicochemical characteristics that contribute to its efficacy⢠and stability. Thisâ white âŁto⤠off-white âŁcrystalline powder has a molecular weight of 299.35 g/mol andâ a melting point ranging from 233°Câ to 240°C. Its chemical formula, C15H13N3O2S, reflects âits composition of⢠carbon, hydrogen, nitrogen, oxygen, andâ sulfur atoms. Fenbendazole âdemonstrates low solubility inâ water (0.01 mg/L at 25°C) but is more â¤soluble in organicâ solvents such as dimethyl sulfoxide and dimethylformamide.
The â¤stability of â¤fenbendazole⣠is a âcrucial factorâ in its âshelf life and âŁeffectiveness. it remains stable⣠underâ normal storage conditions, with a⣠recommended storage temperature below 30°C. â˘Though, âexposure to âextreme heat, moisture, or direct sunlight can lead to degradation.The compound’s stability â˘is enhanced⢠byâ its⤠abilityâ to form stable complexes with⢠cyclodextrins, âwhich canâ improve its solubility and bioavailability. Fenbendazole’s chemical â˘structure,notablyâ the âpresence of a benzimidazole ring,contributes âto its resistance âŁagainst enzymatic breakdown,allowing for prolonged activity⢠withinâ the body.
| Property | Value |
|---|---|
| Molecular Formula | C15H13N3O2S |
| Melting Point | 233-240°C |
| Waterâ Solubility | 0.01 mg/L at 25°C |
| Appearance | White to off-white crystalline powder |
Mechanismâ of âAction and Pharmacokinetics
Fenbendazoleâ exertsâ its antiparasitic effects by bindingâ to β-tubulin, disrupting âŁmicrotubule formation in parasitic âcells. This interference leads to impaired glucose â¤uptake,depleted energy â¤reserves,and ultimately,parasite death. âThe drug’s selective â˘toxicity stems âfrom its higher⢠affinity for âparasite tubulin compared to mammalian tubulin. Additionally, fenbendazole inhibits the fumarateâ reductase âsystem, further compromising the parasite’s energy metabolism.
Upon âoral administration, fenbendazoleâ undergoes âextensive first-passâ metabolismâ in âthe liver.The primary metabolite,⣠oxfendazole, contributes significantly to the drug’s antiparasiticâ activity. Fenbendazole exhibits poor âwater solubility, leading to⤠variable absorptionâ rates across⤠species.⤠In most⢠animals, peak⢠plasma â˘concentrations⢠are reached âŁwithinâ 6-30 hours after ingestion.the⤠drug andâ its⣠metabolites are primarily excreted in feces, with⢠a â¤smaller portion âeliminated⣠through âurine. Notably, fenbendazole’s elimination half-life varies considerably among species:
- Cattle: 10-27 âhours
- Sheep: 8-15 hours
- Horses: 9-18 hours
- Dogs: 7-19 â¤hours
Veterinary âApplications âand Dosage Recommendations
In veterinary âmedicine, fenbendazole â˘playsâ a crucial⣠role in treating various âŁparasitic infections inâ animals. â¤It is â˘indeed âŁcommonly âusedâ to combatâ gastrointestinal nematodes, lungworms, and certain protozoan parasites⣠in livestock, companion animals, â˘and⣠wildlife. The drug’s broad-spectrum efficacy makesâ it âa valuable tool for veterinarians inâ managing parasitic diseases⤠across different species.
Dosage recommendations âfor â˘fenbendazole vary depending⢠onâ theâ animal species, body â˘weight, âŁand specific â¤parasite⢠being targeted. General guidelines include:
- Cattle:⤠5-10 mg/kg âbodyâ weight
- Sheep⣠and goats: 5 mg/kgâ body âŁweight
- Horses: 7.5-10⣠mg/kg body âŁweight
- Dogs and cats: 50 mg/kg body âweight daily for⤠3-5 âdays
| Animal | Typical âŁDuration | Administration Route |
|---|---|---|
| Livestock | Single dose | Oral suspension |
| Pets | 3-5 days | Tablets or liquid |
Potential Human Usesâ and Clinical Trials
Recent studies have âŁexplored the potential of fenbendazole in humanâ medicine, particularly âinâ cancer treatment. Researchers have observed anti-tumor effects in⢠various cancer cell lines,⢠including lung, breast,⢠and⢠colorectal⣠cancers.these⣠findings have sparked interest in repurposing this veterinary drug forâ human use,with several â ongoing clinical âtrials investigating its efficacy and safety profile in cancer patients.
Beyond oncology, fenbendazole’s antiparasitic properties âhave âŁled⤠to âinvestigations into âits use against humanâ parasitic infections.â Preliminary⤠research suggests it may be effectiveâ against:
- Giardiasis
- Cryptosporidiosis
- Soil-transmitted helminth âinfections
Additionally, scientists areâ exploringâ its potential as an antifungal agent and its role in modulating the immune system. As research âprogresses, fenbendazole could become⤠a valuable addition to the arsenal of human âmedical treatments.
Safety Profile and⤠Environmental Impact ofâ Fenbendazole
Fenbendazole exhibits a⢠favorable â˘safety profile when used as directed in veterinary applications. Its low toxicity to âŁmammals and selective action⢠against parasites â¤make it a preferred choice âforâ treating various⣠animalâ species. Though, caution â¤is advised for pregnant animals and those with liver conditions. In rare cases,⢠mild side⤠effects such as vomiting or⤠diarrheaâ may occur. It’s âimportant to note thatâ whileâ fenbendazole isâ generallyâ well-tolerated, off-label use in humans or improper dosing can lead to⢠adverse effects.
regarding environmental impact, fenbendazole demonstrates relatively âlow â˘persistence⣠inâ soil and âwater systems. âItâ undergoes⣠gradual degradationâ through natural⢠processes, minimizing âlong-term accumulation.Though, â¤concerns exist â˘about its potential effects on non-target organisms, particularly aquatic⣠invertebrates and âŁsome soil-dwelling species. To mitigateâ risks, proper disposal âof unused medication and animalâ wasteâ containing fenbendazole residues is crucial. âOngoing research aims to further understand and address any âpotential ecological implications associated with widespread use of⤠this antiparasitic compound.
- Key safetyâ considerations:
- Low mammalian toxicity
- Cautionâ for⢠pregnant animals
- Possible mild side effects
- Environmental factors:
- Limited âsoil and water persistence
- Potential impact on ânon-targetâ organisms
- Proper⤠disposal practices recommended
Q&A
Q: What is fenbendazole?
A: Fenbendazole is a broad-spectrum anthelmintic medication âbelonging to the benzimidazole âclass of⢠compounds.
Q: What is â¤the chemical⤠formula ofâ fenbendazole?
A: The âchemical formula of fenbendazole is âC15H13N3O2S.
Q: What areâ the⤠physical â¤propertiesâ of fenbendazole?
A: Fenbendazole isâ a âwhite to off-white crystalline solidâ with a melting point of approximately 233°C (451°F).
Q: Is fenbendazole âsoluble in â¤water?
A: Fenbendazole has vrey low solubility â˘in water, butâ it is soluble in organic solvents such⣠as dimethyl sulfoxide (DMSO).
Q: What is the primary veterinaryâ use ofâ fenbendazole?
A: Fenbendazole âis primarily used â¤as an antiparasitic medication to treat various âintestinal wormsâ in animals, including roundworms, hookworms, and âwhipworms.
Q: Does fenbendazole have any âapplications in human medicine?
A: While primarily âused âŁin veterinary medicine, âŁfenbendazole has been investigated for potential applications inâ human medicine, particularly âin cancer research.
Q: âHow does fenbendazole âŁwork as⢠anâ anthelmintic?
A: Fenbendazole works by binding â¤to tubulin in parasitic cells, disrupting⢠cell division and energy metabolism, which leads to the death of theâ parasites.
Q:⤠What isâ the typical dosage âformâ of fenbendazole?
A: Fenbendazole is commonly⣠available⤠as oral âsuspensions, âŁtablets, or granules âfor veterinary use.
Q: Are there any known drug âinteractions with fenbendazole?
A: Fenbendazole may interact with other⣠medications metabolized by⣠the liver, but âdrug interactions are⣠generally considered minimal âwhen used as directed in veterinary applications.
Q: âWhat are someâ potential side effects of fenbendazole in âanimals?
A: Side⢠effects in animals are â˘generally rare but may include vomiting, diarrhea, or âloss of appetite in some cases.
Insights and conclusions
fenbendazole’s unique chemical properties make⣠it a âversatile compound with applications⢠spanning veterinary⢠medicine, âŁagriculture,⢠and âŁpotential human treatments. Its broad-spectrum â˘anthelmintic activity,⤠coupled with its relatively low toxicity to mammals, has established it âas a valuable tool in parasite control. As â¤research⢠continues, further⤠understanding of fenbendazole’s mechanisms of action and potential newâ applications â˘may expand its utility in â¤various fields.The â¤ongoing study of this â˘benzimidazole derivative underscores the importance âŁof â¤continued investigation into antiparasitic agents and âŁtheirâ diverse âŁroles in health⣠and agriculture.
