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| Other Sizes |
| Targets |
Albendazole oxide targets tubulin, a protein that polymerizes to form microtubules, which are essential components of the cytoskeleton and play a critical role in cellular division, intracellular transport, and maintenance of cell shape. By binding to tubulin, Albendazole oxide inhibits its polymerization, thereby disrupting microtubule formation. This disruption interferes with the mitotic spindle formation during cell division, leading to the immobilization and death of parasites. The compound's selective toxicity for parasites over host cells is due to its higher affinity for parasite tubulin. Albendazole oxide is the active metabolite of albendazole and is responsible for the drug's anthelmintic activity.
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| ln Vitro |
Escherichia multilocularis is susceptible to the parasiticidal effects of albendazole sulfoxide (10 μg/mL, 3–16 days) [2].
In vitro studies have demonstrated that Albendazole oxide is a potent inhibitor of tubulin polymerization. It disrupts microtubule formation in parasite cells, leading to the immobilization and death of the parasites. In vitro culture of Echinococcus multilocularis has shown that albendazole sulphoxide at concentrations of 500 µg/L significantly reduces protoscolex viability. The compound's activity against various parasites, including nematodes, tapeworms, and trematodes, has been characterized in vitro. These studies confirm that Albendazole oxide is a potent anthelmintic agent with activity against a broad range of parasitic worms. |
| ln Vivo |
In Balb/c mice infected with protoscoleces, albendazole sulfoxide (0.5 mg/kg, surgical injection, BID, 15 days) decreases cyst size and weight [3].
In vivo studies have demonstrated that Albendazole oxide is effective in treating parasitic infections in livestock and poultry. It is used for the treatment of nematode disease, tapeworm disease, and trematodiasis. The compound is the active metabolite of albendazole and is responsible for its anthelmintic activity in vivo. Pharmacokinetic studies have shown that albendazole is metabolized to albendazole sulphoxide (Albendazole oxide), which is the active metabolite. The pharmacokinetics of albendazole sulphoxide have been studied in humans, showing marked inter-individual variation in maximum plasma concentration and area under the curve. Albendazole oxide is used in veterinary medicine to treat parasitic infections in livestock and poultry. |
| Enzyme Assay |
The in vitro assays for Albendazole oxide measure its effects on tubulin polymerization and parasite viability. Tubulin polymerization assays typically involve incubating purified tubulin with Albendazole oxide and measuring the formation of microtubules spectrophotometrically. The inhibition of polymerization is calculated, and the IC50 is determined. Parasite viability assays involve culturing parasites (e.g., Echinococcus multilocularis protoscoleces) with varying concentrations of Albendazole oxide and assessing viability using vital dye exclusion or other methods. These assays confirm the compound's mechanism of action and its potency against parasites.
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| Cell Assay |
In vitro cell-based assays for Albendazole oxide are used to study its effects on parasite cells and its cytotoxicity. Parasite cultures (e.g., protoscoleces of Echinococcus multilocularis) are treated with varying concentrations of Albendazole oxide, and viability is assessed using vital dye staining or by measuring metabolic activity. The compound's effects on mammalian cells can also be assessed to determine its selectivity. These cell-based assays confirm that Albendazole oxide is a potent inhibitor of parasite growth with selective toxicity for parasites over host cells.
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| Animal Protocol |
In vivo animal experiments for Albendazole oxide are conducted in livestock and poultry to evaluate its efficacy against parasitic infections. In a typical study, animals naturally or artificially infected with parasites are treated with Albendazole oxide or its parent drug albendazole. The efficacy is assessed by measuring the reduction in parasite egg counts in feces (fecal egg count reduction, FECR) or by examining the animals for the presence of parasites at necropsy. Pharmacokinetic studies are also conducted to determine the absorption, distribution, metabolism, and excretion of the compound. These studies are essential for evaluating the efficacy and safety of Albendazole oxide in veterinary medicine.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Albendazole oxide is a known metabolite of albendazole in the human body. Albendazole oxide has a molecular weight of 281.33 g/mol and a molecular formula of C12H15N3O3S. It has a melting point of 154-156°C, a boiling point of 357.3°C, and a density of 1.458 g/cm³. The compound is supplied as a white to off-white powder with a purity of >98%. It is soluble in DMSO and other organic solvents. For storage, it is recommended to keep the powder at -20°C. Pharmacokinetic properties have been studied, and albendazole oxide is the major active metabolite of albendazole. |
| Toxicity/Toxicokinetics |
Albendazole oxide is a metabolite of albendazole and shares its toxicity profile. Albendazole is generally well-tolerated, but it can cause gastrointestinal disturbances, headache, and dizziness. In rare cases, it can cause hepatotoxicity, bone marrow suppression, and other serious adverse effects. Albendazole oxide is contraindicated in patients with hypersensitivity to benzimidazoles and in pregnant women. As a veterinary drug, it is used at doses that are effective against parasites while minimizing toxicity to the host. As with all chemicals, standard laboratory safety precautions should be followed when handling Albendazole oxide.
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| References |
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| Additional Infomation |
Albendazole S-oxide is a sulfoxide. It is functionally related to albendazole. Albendazole oxide has been reported to be detected in Penicillium solitum and Penicillium crustosum, and relevant data are available.
Albendazole oxide (Ricobendazole) is the major active metabolite of the anthelmintic drug albendazole. It is a tubulin polymerization inhibitor that disrupts microtubule formation in parasites. Albendazole oxide is used for the treatment of livestock and poultry nematode disease, tapeworm disease, and trematodiasis. It has been reported in Penicillium solitum and Penicillium crustosum. The compound's mechanism of action involves binding to tubulin and inhibiting its polymerization, leading to the disruption of microtubule formation and the death of parasites. Albendazole oxide is a research compound and a veterinary anthelmintic, and it is not approved for human use in many countries. |
| Molecular Formula |
C12H15N3O3S
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| Molecular Weight |
281.3308
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| Exact Mass |
281.083
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| CAS # |
54029-12-8
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| Related CAS # |
Albendazole sulfoxide-d3;1448346-38-0;Albendazole;54965-21-8;Albendazole sulfoxide-d7;2469575-37-7
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| PubChem CID |
83969
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
357.3ºC at 760 mmHg
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| Melting Point |
154-156ºC
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| Flash Point |
169.9ºC
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| Index of Refraction |
1.659
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| LogP |
0.91
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
19
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| Complexity |
353
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VXTGHWHFYNYFFV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
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| Chemical Name |
methyl N-(6-propylsulfinyl-1H-benzimidazol-2-yl)carbamate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~88.86 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5545 mL | 17.7727 mL | 35.5454 mL | |
| 5 mM | 0.7109 mL | 3.5545 mL | 7.1091 mL | |
| 10 mM | 0.3555 mL | 1.7773 mL | 3.5545 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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