methyl N-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]carbamate

• ChemBase ID: 73243
• Molecular Formular: C12H15N3O3S
• Molecular Mass: 281.3308
• Monoisotopic Mass: 281.08341236
• SMILES: c1(ccc2c(c1)[nH]c(n2)NC(=O)OC)S(=O)CCC
• Canonical SMILES: CCCS(=O)c1ccc2c(c1)[nH]c(n2)NC(=O)OC
• InChI: 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)
• InChIKey: VXTGHWHFYNYFFV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]carbamate; methyl N-[5-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]carbamate
• IUPAC Traditional name: methyl N-[5-(propane-1-sulfinyl)-3H-1,3-benzodiazol-2-yl]carbamate; (+-)-albendazole sulfoxide
• Synonyms: Ricobendazole; Albendazole Oxide; Albendazole sulfoxide; Albendazole Oxide, Ricobendazole, RS-8852, Albendazole Impurity B (EP),; Albendazole Sulfoxide; Albendazole oxide; Albendazole sulfoxide; Methyl [5-(propane-1-sulfinyl)-1H-benzoimidazol-2-yl]-carbamate; Ricobendazole; methyl n-(6-propylsulfinyl-1h-benzoimidazol-2-yl)carbamate

Database IDs

• CAS Number: 54029-12-8
• MDL Number: MFCD00797922
• Beilstein Number: 677664
• PubChem SID: 162038163
• PubChem CID: 83969

CALCULATED PROPERTIES

• Acid pKa: 8.734701
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.552342
• LogD (pH = 7.4): 1.5483265
• Log P: 1.5656897
• Molar Refractivity: 74.5348 cm^3
• Polarizability: 29.355896 Å^3
• Polar Surface Area: 84.08 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (Sparingly); Methanol
• Apperance: White to Off-White Solid
• Melting Point: 226-228°C dec.

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: FD1080000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC); 97%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H15N3O3S

DETAILS

Selleck Chemicals - S1836

Research Area: Infection
Biological Activity:

Sigma Aldrich - 19953

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.2
Application
Ricobendazole is a methylcarbamate benzimidazole with a broad-spectrum anthelmintic activity. Ricobendazole is a key metabolite of albendazole 1. 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.2

Sigma Aldrich - 35395

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.1
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A511620

A metabolite of Albendazole, an anthelmintic.

REFERENCES

• Dominguez, L., et al.: Farmaco, 50, 697 (1995)
• De Laurentis, N., et al.: Pharm. Pharmacol Lett., 6, 2: 51 (1996)