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Merck
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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:
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.

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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
Viviane Cangerana Hilário et al.
Journal of pharmaceutical and biomedical analysis, 61, 100-107 (2012-01-11)
A high-performance liquid chromatographic method using polar organic mode was developed to analyze albendazole (ABZ), albendazole sulfone (ABZSO(2)) and the chiral and active metabolite albendazole sulfoxide (ABZSOX, ricobendazole) that was further applied in stereoselective fungal biotransformation studies. The chromatographic separation
Mesküre Capan et al.
The American journal of tropical medicine and hygiene, 81(4), 712-713 (2009-10-10)
Albendazole therapy--alone or in combination with surgery--remains the standard of care for human echinococcosis depending on the stage of disease. However, only limited data are available on target site concentrations in liver cysts and data for non-liver cysts are lacking.
Kathrin Eckardt et al.
Reproductive toxicology (Elmsford, N.Y.), 34(3), 378-384 (2012-06-02)
The benzimidazole carbamate albendazole (ABZ), a potent anthelmintic, is a teratogenic compound in rats. At present it is unclear to which degree this effect is caused by the parent compound or its major metabolite, albendazole sulfoxide (ASO). Both substances were
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