N-benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide

• ChemBase ID: 146922
• Molecular Formular: C12H12N4O3
• Molecular Mass: 260.24868
• Monoisotopic Mass: 260.09094026
• SMILES: c1ccc(cc1)CNC(=O)Cn1ccnc1[N+](=O)[O-]
• Canonical SMILES: O=C(Cn1ccnc1[N+](=O)[O-])NCc1ccccc1
• InChI: InChI=1S/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)
• InChIKey: CULUWZNBISUWAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-benzyl-2-(2-nitro-1H-imidazol-1-yl)acetamide
• IUPAC Traditional name: benznidazole
• Synonyms: N-Benzyl-2-nitro-1H-imidazole-1-acetamide; 2-Nitro-N-(phenylmethyl)-1H-imidazole-1-acetamide; N-Benzyl-2-nitro-Imidazole-1-acetamide; Benznidazole; Benzonidazol; Benzonidazole; N-Benzyl-2-nitroimidazol-1-yl-acetamide; NSC 299972; Radanil; Ro 07-1051; Ro 71051; Rochagan; Benznidazole; 苄哒唑

Database IDs

• CAS Number: 22994-85-0
• MDL Number: MFCD00243089
• PubChem SID: 24866267; 162241114
• PubChem CID: 31593

CALCULATED PROPERTIES

• Acid pKa: 14.404373
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3218759
• LogD (pH = 7.4): 1.3218759
• Log P: 1.3218759
• Molar Refractivity: 68.1236 cm^3
• Polarizability: 25.411263 Å^3
• Polar Surface Area: 92.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 189-192 °C(lit.)

Safety Information

• RTECS: NI3340000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C12H12N4O3

DETAILS

Sigma Aldrich - 419656

Packaging
1 g in glass bottle

Toronto Research Chemicals - B197925

Benznidazole (BNZ) is traditionally used to treat Chagas disease caused by Trypanosoma cruzi. The drugs used for the treatment of this disease, Nifurtimox and Benznidazole, are toxic and present severe side effects.

REFERENCES

• Abuin, G., et al.: Mol. Biochem. Parasitol ., 35, 229 (1989)
• Arora, P., et al.: J. Biol. Chem., 270, 6042 (1989)
• Campos, M., et al.: J. Immunol., 167, 416 (1989)
• Faundez, M., et al.: Antimicrob. Agents Chemother., 49, 126 (1989)