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SMB01325

Sigma-Aldrich

Albendazole sulfoxide

≥97% (HPLC)

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Synonym(s):
Ricobendazole, Albendazole oxide, Albendazole sulfoxide, Methyl [5-(propane-1-sulfinyl)-1H-benzoimidazol-2-yl]-carbamate
Empirical Formula (Hill Notation):
C12H15N3O3S
CAS Number:
54029-12-8
Molecular Weight:
281.33
Beilstein:
677664
MDL number:
MFCD00797922
UNSPSC Code:
12352119
NACRES:
NA.77

description

Modulation and Signaling

Quality Level

100

Assay

≥97% (HPLC)

form

solid

color

white to beige

suitability

HPTLC

storage temp.

2-8°C

SMILES string

CCCS(=O)c1ccc2[nH]c(NC(=O)OC)nc2c1

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)

InChI key

VXTGHWHFYNYFFV-UHFFFAOYSA-N

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General description

Albendazole sulfoxide is a blood-brain barrier main metabolite of anti-parasitic agent albendazole that acts as a antihelminthic. It binds to colchicine binding site of β-tubulin and prevents polymerization. Albendazole sulfoxide exhibits greater affinity to parasitic β-tubulin than to mammalian.

Application

Metabolomics research

Biochem/physiol Actions

Ricobendazole is a key metabolite of albendazole and acts as an anthelmintic. It has been shown to induce apoptosis in human cancer cell line HT-29, possibly by arresting cell cycle at the G2/M phase.

Other Notes

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Signal Word

Warning

Hazard Statements

H317,H361d,H373,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 2 - Skin Sens. 1 - STOT RE 2 Oral

Target Organs

Adrenal gland,spleen,male reproductive organs,Blood

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Lidia Radko et al.
Journal of veterinary research, 61(3), 313-319 (2018-07-07)
Albendazole is used to treat endoparasitic diseases in animals and humans. After oral administration, it is quickly oxidised into its pharmacologically active metabolite albendazole sulfoxide and then to sulfone. However, it is not clear which compound is responsible for toxic
Maximo Pettarin et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 155, 105552-105552 (2020-09-17)
The aim of this study was to use a combined in vitro-in silico approach to develop a physiologically based pharmacokinetic model (PBPK) that predicts the bioavailability of albendazole (ABZ), a BCS class II/IV lipophilic weak base, and simulates its main

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