methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate

• ChemBase ID: 157693
• Molecular Formular: C12H15N3O4S
• Molecular Mass: 297.3302
• Monoisotopic Mass: 297.07832698
• SMILES: CCCS(=O)(=O)c1ccc2c(c1)nc([nH]2)NC(=O)OC
• Canonical SMILES: CCCS(=O)(=O)c1ccc2c(c1)nc([nH]2)NC(=O)OC
• InChI: InChI=1S/C12H15N3O4S/c1-3-6-20(17,18)8-4-5-9-10(7-8)14-11(13-9)15-12(16)19-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
• InChIKey: CLSJYOLYMZNKJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• IUPAC Traditional name: methyl N-[5-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]carbamate
• Synonyms: Methyl [5-(propylsulfonyl)-1H-benzimidazol-2-yl]carbamate; Albendazole sulfone; Methyl 5-n-propylsulfonyl-2-benzimidazolecarbamate; N-[6-(Propylsulfonyl)-1H-benzimidazol-2-yl]carbamic Acid Methyl Ester; Methyl [5-(propylsulfonyl)-1H-benzimidazol-2-yl]carbamate, Albendazole Impurity C (EP),; Albendazole Sulfone; Alben; Bermosol; Eskazole; Helmintal; Valbazen; Zentel; 阿苯达唑砜

Database IDs

• CAS Number: 75184-71-3
• MDL Number: MFCD00600775
• Beilstein Number: 8394880
• PubChem SID: 162251830
• PubChem CID: 53174

CALCULATED PROPERTIES

• Acid pKa: 8.719393
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6716211
• LogD (pH = 7.4): 1.6547793
• Log P: 1.6725836
• Molar Refractivity: 74.1216 cm^3
• Polarizability: 29.929394 Å^3
• Polar Surface Area: 101.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 290-292°C; 296-298°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DD6520700
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63; 63-36/38
• Safety Statements: 26-36/37; 36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H361d; H361
• GHS Precautionary statements: P281-P201-P202-P308+P313-P405-P501A; P281-P305 + P351 + P338

Pharmacology Properties

• Mechanism of Action: Also has been shown to inhibit the enzyme fumarate reductase, which is helminth-specific.; Causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin,; Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP),; Due to diminished energy production, the parasite is immobilized and eventually dies.; The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores.; This action may be considered secondary to the effect; thus inhibiting its polymerization or assembly into microtubules.; which is the energy required for the survival of the helminth.

Product Information

• Grade: VETRANAL™, analytical standard
• Application(s): Anthelmintic; Investigated for treatment of chronic stronglyoidiasis, and for microsporidiosis in AIDS patients
• Empirical Formula (Hill Notation): C12H15N3O4S

DETAILS

Sigma Aldrich - 35394

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

Toronto Research Chemicals - A511615

A metabolite of Albendazole, an anthelmintic.

REFERENCES

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