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Merck

35395

Albendazole sulfoxide

VETRANAL®, analytical standard

Synonym(s):

Ricobendazole, Albendazole oxide, Albendazole sulfoxide, Methyl [5-(propane-1-sulfinyl)-1H-benzoimidazol-2-yl]-carbamate

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About This Item

Empirical Formula (Hill Notation):
C12H15N3O3S
CAS Number:
54029-12-8
Molecular Weight:
281.33
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329755155
MDL number:
MFCD00797922
Beilstein/REAXYS Number:
677664

Key Documents

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InChI key

VXTGHWHFYNYFFV-UHFFFAOYSA-N

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)

SMILES string

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

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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Warning

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ6166
BCCG3899
BCCD7646
BCCC5377
BCCB7338

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Hai-Jun Gao et al.
Parasites & vectors, 14(1), 108-108 (2021-02-17)
Echinococcosis, which is caused by the larvae of cestodes of the genus Echinococcus, is a parasitic zoonosis that poses a serious threat to the health of humans and animals globally. Albendazole is the drug of choice for the treatment of
Adriana Paredes et al.
Antimicrobial agents and chemotherapy, 57(2), 944-949 (2012-12-12)
Albendazole is an anthelmintic drug widely used in the treatment of neurocysticercosis (NCC), an infection of the brain with Taenia solium cysts. However, drug levels of its active metabolite, albendazole sulfoxide (ABZSO), are erratic, likely resulting in decreased efficacy and
A Dib et al.
Journal of veterinary pharmacology and therapeutics, 34(2), 136-141 (2011-03-15)
New therapeutic strategies based on the search of alternative formulations of albendazole (ABZ) and albendazole sulphoxide (ABZSO) are under current development to optimize posology and antiparasite efficacy in dogs. In an incomplete block design, nine dogs were randomly divided into
Steven T Laing et al.
The Biochemical journal, 432(3), 505-514 (2010-10-12)
Knowledge of how anthelmintics are metabolized and excreted in nematodes is an integral part of understanding the factors that determine their potency, spectrum of activity and for investigating mechanisms of resistance. Although there is remarkably little information on these processes
Miriam Teruel et al.
Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al, 35(1), 29-33 (2011-06-15)
Benzimidazole compounds are used in both humans and animals for controlling helminth parasites. Albendazole has teratogenic effects attributed to its active metabolite albendazole sulphoxide. The aim of this work was to evaluate the effect of the latter compound when administered
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