Fenbendazole: Chemical Properties and Classification
Fenbendazole, âa widely used anthelmintic drug in veterinary medicine, belongs to the benzimidazole âclass of compounds. âThis article explores the chemical properties and classification of fenbendazole,providing an overview of its molecular âŁstructure,physical characteristics,and pharmacological categorization. Understandingâ these aspects is âessential for researchers,⣠veterinarians, and pharmaceutical professionals working with this significant antiparasitic agent.
Table âof Contents
- Chemical Structure and Molecular Properties of Fenbendazole
- Pharmacological Classification and Mechanism of Action
- Physical Characteristics and â˘Stability âof Fenbendazole
- Synthesis and Manufacturing Process of Fenbendazole
- Analytical Methods⣠for Fenbendazole Detection⣠and Quantification
- Regulatory Status and applications in Veterinary Medicine
- Q&A
- Key Takeaways
Chemical âStructure and Molecular⤠Properties of Fenbendazole
Fenbendazole is aâ benzimidazole compound with â˘the molecular⣠formula C15H13N3O2S.Its systematic name is methyl N-[6-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate. The compound features a benzimidazole core structure with a phenylthio group attached at the 6-position âand a methylcarbamateâ moiety linked to the 2-position.â This arrangement of atoms contributes toâ its unique chemical properties and biologicalâ activity.
Key molecular properties of fenbendazole include:
- Molecular weight: â 299.35 g/mol
- LogP: 3.3 (indicating moderate lipophilicity)
- Hydrogen bond donors: 2
- Hydrogen bondâ acceptors: 4
- Rotatable bonds: 4
These properties contribute to fenbendazole’s ability⢠to penetrate cell membranes and interact⢠with its target proteins. The compound’s relatively low solubility in water â(approximately 0.007 mg/mL at 25°C) influencesâ its pharmacokinetic behaviorâ and necessitates specific formulation strategies for â˘effective⣠drug delivery.
Pharmacological Classification and Mechanism of Action
Fenbendazole belongsâ to the benzimidazole class of anthelmintic drugs, which â˘are widely used for treating parasitic â˘worm infections⢠in both humans and animals.Its primaryâ mechanism of actionâ involves binding to β-tubulin in parasiticâ cells, disrupting â¤microtubule formation and ultimately leading to the deathâ of âthe parasite. Thisâ selective toxicity allows fenbendazole to effectively target helminths while minimizing adverse effects on the host âorganism.
along withâ its anthelmintic properties, fenbendazole has shown⣠potential â˘as anâ anticancer agent. Recent studies suggest that⤠it may⤠inhibit glucose uptake in cancer cells, interfere with microtubule â˘formation, and induce apoptosis⤠in tumor cells.⣠These multifaceted pharmacological effects have sparked interest in repurposing fenbendazole for various therapeutic applications beyond its âtraditional use as an antiparasitic⣠medication.
- Primary classification: Benzimidazole⢠anthelmintic
- Secondary classification: Potential anticancer agent
- Key mechanisms: ⤠β-tubulin binding, microtubule disruption, glucose uptake inhibition
Physical Characteristics and Stability of Fenbendazole
Fenbendazole presents as a white to off-white âŁcrystalline solid at room temperature. Its⤠molecular structure consists ofâ a benzimidazole ring fused with a carbamate group, contributing to its unique chemical properties. This compound exhibits low solubility âin water but dissolves readily âin organic solvents such as dimethyl sulfoxide⤠(DMSO) and methanol. The â¤melting point of fenbendazole typically ranges between 233°C and 240°C, indicating its âthermal stability under normalâ conditions.
The stability⤠of fenbendazole is a crucial factor âin its storage and request. This compound âdemonstratesâ remarkable resilience to environmental factors, maintaining its efficacy for extended periods when â˘stored properly.⢠However,exposure to⤠extreme temperatures,humidity,orâ direct sunlightâ may compromise its structural integrity.To ensure optimal stability,⣠it is indeed recommended⢠to store fenbendazole in the following conditions:
- Keep in a cool, dry⤠place
- Protect from direct light exposure
- Storeâ in airtight containers
- Avoid temperature fluctuations
Note: Adherence âto proper storage guidelines is essential for maintaining the compound’s effectiveness and safety profile.
Synthesis and⢠Manufacturing Process of Fenbendazole
The production of fenbendazole involves a multi-step chemical âŁprocess that begins with⢠the synthesis of its core structure.Chemists typically start with 2-aminobenzimidazole as the primary â˘building block, which undergoes⣠a series of reactions to form the benzimidazole carbamate skeleton. This intermediate compound is then⢠further modified through alkylation and sulfuration steps to yieldâ the final fenbendazole molecule.
Industrial-scale manufacturing of âfenbendazole⤠relies on carefully controlled conditions to ensure highâ purity and yield. Key aspects â¤of the process include:
- Temperature regulation during â˘critical reactionâ stages
- Precise pH control âto optimize⤠product formation
- Solvent selection âfor efficient extraction â¤and⤠purification
- Specialized filtration techniques to remove impurities
| Process Step | Key Parameters |
|---|---|
| Core synthesis | 60-80°C, 4-6 hours |
| Alkylation | pH 8-9, inert âŁatmosphere |
| Purification | Recrystallization,â 95% yield |
Analytical Methods for Fenbendazole Detection and â˘Quantification
Several refinedâ techniques are âemployed to detect and quantify âfenbendazole inâ various matrices. High-performance liquid chromatography (HPLC) coupled with âŁUV detection is widely used due to its sensitivity and accuracy. This method allows for precise separation⤠and identification of fenbendazole and its metabolites. Additionally, ⣠liquid chromatography-mass âspectrometry âŁ(LC-MS) offers enhanced selectivity and lower detection limits, making it⢠ideal for trace analysis in⣠complex⣠biological samples.
Other analytical approaches include:
- Gas chromatography-mass spectrometry (GC-MS)
- Enzyme-linked immunosorbent assay (ELISA)
- Thin-layer chromatography (TLC)
Each method has â¤its strengths â˘and limitations, with selection⤠depending on factors such as âsample type, âŁrequired sensitivity, and available â¤resources. Researchers continue â˘to develop and refine theseâ techniques to improve detection limits and expand their applicability across various⢠matrices, âŁfrom pharmaceutical formulations to environmental samples.
Regulatory⣠Status and Applications in Veterinary Medicine
fenbendazole’s use in veterinary medicine is subject to various regulatory frameworks across⤠different countries. âŁInâ the United â¤States, it is indeed⢠approved by⢠the Food and Drug⤠Administration (FDA) for use in multiple animal â¤species, including cattle, horses, dogs, and⣠cats. The European Medicines Agency (EMA) has also authorized its use⣠in veterinary practice within the European Union. Though, regulations may vary in other regions, and veterinarians must adhere âto local guidelines when prescribing this anthelmintic drug.
The applications of fenbendazole in veterinary medicine are diverse, targeting a wide range of âparasitic infections. It is commonly used to treat:
- Gastrointestinal roundworms
- lungworms
- Tapeworms in some species
- Certain protozoan infections
Its broad-spectrum efficacy and relatively low toxicity âŁmake it a valuable tool in veterinaryâ practice. Though, as with â˘anyâ medication, proper dosing and administration are crucial to ensureâ both safety and⤠effectiveness in treating parasitic infections in âanimals.
Q&A
Q: What is fenbendazole?
A: Fenbendazole is a broad-spectrum anthelmintic medication used primarily in veterinary medicine to treat various parasitic worm infections in âanimals.
Q: What is the chemical formula âof Fenbendazole?
A: Theâ chemical formulaâ of Fenbendazole is C15H13N3O2S.
Q: what is the IUPAC name for Fenbendazole?
A: The IUPAC name for Fenbendazole isâ Methyl N-[6-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate.
Q: What is the molecular weight of â˘Fenbendazole?
A:â The molecular weight of Fenbendazole is â299.35 g/mol.
Q: What is âthe physical appearance of âFenbendazole?
A: Fenbendazole appears as a white to off-white crystalline solid at⣠roomâ temperature.
Q: Toâ which class of compounds⣠does Fenbendazole belong?
A: Fenbendazole⢠belongs âŁto the benzimidazole class of compounds.
Q: What isâ the â¤mechanism of action of âFenbendazole?
A:â Fenbendazole works by binding â˘to and inhibiting theâ polymerization of tubulin in parasitic worms, disrupting their cellular structure and metabolism.
Q: Is Fenbendazole water-soluble?
A: No, Fenbendazole has very low water solubility. It is practically insoluble in âwater.
Q: In whichâ solvents is Fenbendazole soluble?
A:â Fenbendazole is soluble in dimethylsulfoxide (DMSO) and slightly soluble in methanol and ethanol.
Q: What is âthe melting point of Fenbendazole?
A: âThe melting point of Fenbendazole is approximately⣠233°C (451.4°F).
Key Takeaways
fenbendazole’s chemical properties and classification place âit firmly within the benzimidazole family of âanthelmintic drugs. âIts âmolecularâ structure, solubility characteristics, and mechanism of action contribute to its effectiveness against various⢠parasitic worms. As âa broad-spectrumâ antiparasitic âagent, âfenbendazole continuesâ to play âa âsignificant role inâ veterinary medicine and, increasingly, in⢠potential human applications. Further research into this compound may reveal additional uses and refinements âin its administration and efficacy.
