Albendazole

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Albendazole
Category Others
Catalog number BBF-03783
CAS 54965-21-8
Molecular Weight 265.33
Molecular Formula C12H15N3O2S
Purity 98% by HPLC

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Description

Albendazole is an anthelmintic. It prevents the enzymatic process that causes the parasite to absorb glucose, leading to its death.

Specification

Synonyms SKF-62979; SKF 62979; SKF62979; Eskazole; Zentel; Albenza; Valbazen
Storage Store at -20°C (dark)
IUPAC Name methyl N-(6-propylsulfanyl-1H-benzimidazol-2-yl)carbamate
Canonical SMILES CCCSC1=CC2=C(C=C1)N=C(N2)NC(=O)OC
InChI InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
InChI Key HXHWSAZORRCQMX-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance White to Off-white Solid
Application Mesh headings: anthelmintics, Anticestodalagents, Antiprotozoal agents
Antibiotic Activity Spectrum parasites
Melting Point 193-198°C
Density 1.3±0.1 g/cm3
Solubility Soluble in acetic acid, chloroform
LogP 2.7

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Mechanism Of Toxicity Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Toxicity LD50: 1500 mg/kg (oral,mouse).

Reference Reading

1.Comparison of the Pharmacokinetics of Albendazole and its Major Metabolites after Oral Administration of Albendazole as a Suspension and as a Paste Formulation to Sheep
S. E. MARRINE, J. A. BOGAN, W. VANDAELE*. Zbl. Vet. Med. B, 28, 19-26 (1981)
Albendazole is a member of the benzimidazole group of anthelmintics with broad-spectrum activity against gastro-intestinal roundworms including inhibited larval stages, tapeworms, liver flukes and lungworms in many species. In the ruminant animal the rumen acts as a “reservoir” of undissolved albendazole and rhe slow passage of drug through the rumen serves to maintain concentrations of albendazole or active metabolic products in the more distal parts of the gastro-intestinal tract and in the systemic compartment over a number of days. Ruminal by-pass via the oesophageal (reticular) groove could lead to inferior activity of albendazole. In a previous report on albendazole pharmacokinetics we found little evidence of subsitantial ruminal by-pass with albendazole given orally as a drench (suspension) although small amounts passed (directly to the abomasum in individual sheep.

Spectrum

GC-MS Spectrum - GC-EI-TOF (Non-derivatized)

Experimental Conditions

Instrument Type: GC-EI-TOF
Ionization Mode: positive
Chromatography Type: GC

Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive

Experimental Conditions

Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H15N3O2S
Molecular Weight (Monoisotopic Mass): 265.0885 Da
Molecular Weight (Avergae Mass): 265.331 Da

LC-MS/MS Spectrum - LC-ESI-QFT , negative

Experimental Conditions

Instrument Type: LC-ESI-QFT
Ionization Mode: negative

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H15N3O2S
Molecular Weight (Monoisotopic Mass): 265.0885 Da
Molecular Weight (Avergae Mass): 265.331 Da

1H NMR Spectrum

Experimental Conditions

Solvent: DMSO-d6
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS

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