CAS 43210-67-9 Fenbendazole - Analytical Products / Alfa Chemistry

CAT	APS43210679
CAS	43210-67-9
Structure
MDL Number	MFCD00144301
Synonyms	Fenbendazole, Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate, 2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazole, Axilur, Febendazole, Fenbendazol, Fenbendazole, Fenbion, HOE 881, Methyl 5-(phenylthio)-2-benzimidazolecarbamate, Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamate, Panacur, Safe-Guard, Vigisol
IUPAC Name	methyl N-(5-phenylsulfanyl-1H-benzimidazol-2-yl)carbamate
Molecular Weight	299.35
Molecular Formula	C15H13N3O2S
EC Number	256-145-7
Canonical SMILES	COC(=O)Nc1nc2cc(Sc3ccccc3)ccc2[nH]1
InChI	InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)
InChI Key	HDDSHPAODJUKPD-UHFFFAOYSA-N
REAXYS Number	759077

Description	United States Pharmacopeia (USP) Reference Standard, analytical standard
Accurate Mass	299.0728
Form	neat; gas chromatography (GC): suitable
Format	Neat
Grade	analytical standard
Size	100MG

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CAT	Size	Shipping	Storage Conditions	Description	Price
APS43210679-1	100MG	Ice pack (-20°C)	Freezer	API Family: Matrix - API Family See respective official monograph(s); Product Type: API; Subcategory: British Pharmacopoeia	Inquiry
APS43210679-2	100MG	Room Temperature	+20°C	Subcategory: Pharmaceutical and veterinary compounds and metabolites, EU Methods	Inquiry
APS43210679-3	150MG	Room Temperature	2-8°C Fridge/Coldroom	API Family: Matrix - API Family See respective official monograph(s); Product Type: API; Subcategory: European Pharmacopoeia (Ph. Eur.)	Inquiry
APS43210679-4	250MG	Room Temperature	+5°C	API Family: Matrix - API Family Oxfendazole; Febantel; Fenbendazole; Product Type: API/ Impurity; Subcategory: API standards, Mikromol, Antibiotics, Impurity standards	Inquiry

Case Study

Preparation of fenbendazole methyl-β-cyclodextrin inclusion complexes

Ding, Yili, et al. "Preparation and evaluation of fenbendazole methyl-β-cyclodextrin inclusion complexes." BMC Veterinary Research 20.1 (2024): 214.

Fenbendazole, a benzimidazole anthelmintic agent, is widely used in agriculture and veterinary medicine to treat parasitic infections. Recent studies have also demonstrated its potential as an anti-cancer agent, particularly in drug-resistant cancer cells. However, fenbendazole's poor water solubility (0.3 µg/mL) significantly limits its clinical application as an anticancer drug.
To overcome this limitation, an inclusion complex of fenbendazole with methyl-β-cyclodextrin (M-β-CD) was developed using a single-factor and orthogonal strategy. Fenbendazole was dissolved in formic acid and combined with M-β-CD in an aqueous solution under controlled stirring, temperature, and reaction time. After rotary evaporation and freeze-drying, the inclusion complex was obtained as a powder. The complex exhibited an inclusion rate of 29.2% and an inclusion yield of 89.5%, increasing fenbendazole's water solubility to 20.21 mg/mL-meeting the requirements for anticancer drug delivery.
Structural characterization using differential scanning calorimetry, scanning electron microscopy, and NMR spectroscopy confirmed successful complexation. In vitro pharmacokinetic studies showed that 75% of fenbendazole was released within 15 minutes. In vivo pharmacokinetic analysis revealed increased bioavailability of fenbendazole (138%), its major metabolite oxfendazole (149%), and its minor metabolite oxfendazole (169%). These findings suggest that the fenbendazole-M-β-CD complex enhances solubility and bioavailability, reducing dosing requirements and improving therapeutic outcomes, making it a promising candidate for anticancer drug development.

Fenbendazole (FZ) for Ovarian Cancer Treatment: Enhanced Delivery via PLGA Nanoparticles

Chang, Chi-Son, et al. "Anti-cancer effect of fenbendazole-incorporated PLGA nanoparticles in ovarian cancer." Journal of gynecologic oncology 34.5 (2023): e58.

Fenbendazole (FZ), a benzimidazole anthelmintic, has demonstrated potential as an anti-cancer agent, particularly against epithelial ovarian cancer (EOC). However, its poor water solubility limits its therapeutic application. In this study, FZ was encapsulated in poly(D,L-lactide-co-glycolide) acid (PLGA) nanoparticles (FZ-PLGA-NPs) to improve its systemic delivery and bioavailability for cancer therapy.
FZ-PLGA-NPs were prepared using an oil-in-water emulsion method, where FZ was dissolved in DMSO and mixed with PLGA in chloroform. The mixture was emulsified with a PVA solution using sonication, followed by solvent evaporation under reduced pressure. The resulting nanoparticles were characterized for size, zeta potential, and FZ loading efficiency.
In vitro and in vivo studies, including both cell line models and patient-derived xenografts (PDX), were conducted to evaluate the efficacy of FZ-PLGA-NPs in inhibiting EOC cell proliferation and inducing apoptosis. The FZ-PLGA-NPs demonstrated improved therapeutic efficacy compared to free FZ, offering a promising approach to enhance the bioavailability and anticancer activity of fenbendazole. This nanoparticle-based delivery system represents a significant advancement in overcoming the solubility limitations of FZ, paving the way for its clinical application in ovarian cancer treatment.

Preparation of Nanocrystals for Enhanced Solubility and Bioavailability of Fenbendazole

Melian, Maria Elisa, et al. AAPS PharmSciTech 21 (2020): 1-15.

Fenbendazole (FBZ), a widely used anthelmintic compound, faces limitations due to its poor water solubility, hindering its clinical and veterinary applications. In this study, a novel approach was developed to enhance the solubility and bioavailability of FBZ by preparing self-dispersible nanocrystals (SDNCs). These nanocrystals were synthesized using a media milling technique followed by spray-drying.
The formulation of FBZ was optimized with poloxamer 188 (P188) as the carrier, achieving the best process yield (53%) and re-dispersibility properties. The resultant nanocrystals had an average particle size of 258 nm and a polydispersity index of 0.2, demonstrating superior redispersibility in water. The dissolution profile of FBZ in the SDNC formulation showed a marked improvement, with 80% of FBZ dissolving within 15 minutes, compared to only 14% from the control formulation.
This work presents a promising strategy for enhancing the solubility of FBZ, utilizing SDNC technology. The optimized SDNC formulation provides a significant advancement over traditional drug delivery systems, offering increased dissolution rates and potentially improved therapeutic efficacy, which is crucial for overcoming the solubility limitations of FBZ and improving its clinical utility.