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19953

Sigma-Aldrich

Ricobendazole

≥98% (HPLC)

Synonym(s):

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
Beilstein/REAXYS Number:
677664
MDL number:
MFCD00797922
UNSPSC Code:
51101500
PubChem Substance ID:
329751959

assay

≥98% (HPLC)

form

powder

color

colorless to white

antibiotic activity spectrum

neoplastics
parasites

mode of action

DNA synthesis | interferes
enzyme | interferes
protein synthesis | interferes

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

Chemical structure: benzimidazole

Application

Ricobendazole is a methylcarbamate benzimidazole with a broad-spectrum anthelmintic activity. Ricobendazole is a key metabolite of albendazole . It has been shown to induce apoptosis in human cancer cell line HT-29, possibly by arresting the cell cycle at the G2/M phase.

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.

Packaging

25G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

signalword

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mohammad H Pourgholami et al.
Cancer chemotherapy and pharmacology, 55(5), 425-432 (2004-11-27)
The peritoneal surface remains an important failure site for patients with colorectal cancer. We have recently shown that albendazole (ABZ), a safe and effective anthelmintic drug, has profound antitumor activity in hepatocellular cancer. Furthermore, albendazole also possesses unique physiochemical and
Gracia Merino et al.
Drug metabolism and disposition: the biological fate of chemicals, 33(5), 614-618 (2005-02-11)
Methylcarbamate benzimidazoles [albendazole (ABZ), fenbendazole (FBZ), and their respective sulfoxide derivatives, albendazole sulfoxide (ABZSO) and oxfendazole (OXF)] are therapeutically important anthelmintic agents with low bioavailability. We studied their in vitro interaction with the apical ATP-binding cassette (ABC) drug efflux transporters
Hana Bártíková et al.
Veterinary parasitology, 176(1), 27-33 (2010-11-16)
Albendazole (ABZ) is one of the most important benzimidazole compounds possessing high activity against the lancet fluke, Dicrocoelium dendriticum. ABZ sulphoxide (ABZ.SO) is the main molecule present in the bloodstream of an ABZ-treated host. The aim of this study was
Kátia Roberta A Belaz et al.
Journal of pharmaceutical and biomedical analysis, 66, 100-108 (2012-04-11)
Analytical and semipreparative high performance liquid chromatography methods using polysaccharide-based chiral stationary phases were developed for the enantiomeric resolution of albendazol sulfoxide. The enantioseparation of this compound was evaluated with four chiral stationary phases: cellulose and amylose tris(3,5-dimethylphenylcarbamate), amylose tris[(S)-1-phenylethylcarbamate]
L Alvarez et al.
Journal of veterinary pharmacology and therapeutics, 35(4), 365-372 (2011-08-09)
The gastrointestinal absorption of most drugs follows a first-order kinetics, whereby a constant fraction of the total drug is absorbed in each equal time interval. Although this related absorption principle is applicable to the most of the therapeutically used drugs
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