Albendazole

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Cat Number

API54965218

CAS Number

54965-21-8

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CAS Number

54965-21-8

EINECS

259-414-7

Storage

2-8℃

Synonyms

[5-(propylthio)-1H-benzimidazol-2-yl]carbamic acid, methyl ester; ABZ

Molecular Formula

C12H15N3O2S

Molecular Weight

265.33

Smiles

C(OC)(=O)NC1NC2=CC(SCCC)=CC=C2N=1

Appearance

Colorless crystals

Boiling Point

208-210 ℃

Relative Density

1.26

Standard

USP

pKa

10.72

General Description

Albendazole is an anthelmintic of broad spectrum benzimidazole derivatives used to treat numerous parasitic infestations in humans and animals. It is mainly used against the larval stages of tapeworms and some intestinal nematodes. Albendazole has poor aqueous solubility and has been the focus of many drug delivery systems to enhance systemic bioavailability.

Mechanism of Action

Albendazole specifically targets β-tubulin, the parasitic form of the protein that makes up microtubules. Binding of albendazole causes depolymerization of tubulin into microtubules and leads to degeneration of the intracellular structure as well as glycogen depletion. Without the ability to absorb glucose to replenish its glycogen stores, the parasite becomes immobile and eventually dies.

Application

Clinically, albendazole is often used in trials as a primary treatment for neurocysticercosis and hydatid disease. Albendazole also acts as a baseline intervention for public health officials treating large populations for soil-transmitted helminthiasis.

Malak M determined the insecticidal and genotoxic activities of the veterinary anthelmintic Albendazole (ABZ) on third-instar larvae of fall armyworm (FAW). Leaves were dipped into a solution of ABZ (25 mg mL−1) and presented to larvae while controls were offered untreated leaves. Biological parameters were monitored until the adults closed. Hemolymph was collected from larvae at 24 h and 48 h and analyzed for micronuclei (MN), comet DNA-damage classes and Annexin-V-FITC apoptosis/necrosis profiles.
ABZ decreased larval survival, pupation and adult emergence rates to 16%, 30% and 4%, respectively. Larval and adult longevity decreased from 9-8 days to 4 days while pupal duration increased from 9 to 12 days. Additionally, 64% of eclosing adults were either melanized or incompletely deformed. Hemocytes isolated from treated larvae showed a three-fold increase in MN frequency. Comet assay demonstrated that the percentage of undamaged nuclei decreased by 45%, while after 48 h severe damage increased by 10-fold. Flow-cytometry analysis showed that healthy cells decreased from 94% to 59%, early apoptotic cells increased to 23%, while late apoptotic/necrotic cells comprised 12%.

Fig. 1 The insecticidal and genotoxic activities of Albendazole. (Malak M. 2023)

References

Malak M. Albendazole-induced genotoxicity in the larvae of fall armyworm as a safe environmental tool. SN Applied Sciences, 2023, 5(12): 356.

Mahfufah U et al. created a transdermal delivery system for Albendazole (ABZ), which is used to combat cystic echinococcosis but has low water solubility and oral bioavailability, despite its clinical potential. The drug delivery system had two components: a hydrogel-formed microneedle array (HFM) with a polyethylene glycol (PEG) drug reservoir. Hydrogel-formed microneedles were created by chemically crosslinking polyvinyl alcohol (PVA) and polyvinyl pyrrolidone (PVP) with citric acid.
The HFMs had properties ideal for insertion into skin: upon insertion they were able to penetrate 68% of the way into skin with limited needle height reduction and no skin damage. Additionally, these HFMs were capable of swelling over 500% after absorbing the interstitial fluid. The HFMs paired with a PEG drug reservoir allowed transdermal delivery of ABZ.

Fig. 2 Hydrogel-formed microneedles for Albendermal delivery. (Mahfufah U.; et al. 2023)

References

Mahfufah U.; et al. Application of multipolymers system in the development of hydrogel-forming microneedle integrated with polyethylene glycol reservoir for transdermal delivery of albendazole. European Polymer Journal, 2023, 183: 111762.

What research applications is Albendazole commonly used for?

Treatment studies of parasitic infections are its most common use. Albendazole has also been used in cancer research for its potential anti-cancer properties.

How does Albendazole compromise parasite energy metabolism?

Through microtubule interference, albendazole starves parasites by inhibiting glucose uptake. Eventually, parasite glycogen stores are depleted causing energy metabolism failure.

What is the suggested storage method?

Storage in a cool, dry area away from sunlight in air tight containers is suggested.

Is Albendazole useful for animal health research?

Albendazole is commonly used as a research reagent for livestock and domestic animal parasite control.

Does Albendazole affect both adult and larval forms of parasites?

Yes, Albendazole is unique in that it has activity against both adult worms as well as larval stages.