M1547

Metronidazole

BioXtra

• Synonym(s): 2-Methyl-5-nitroimidazole-1-ethanol
• Empirical Formula (Hill Notation): C₆H₉N₃O₃
• CAS Number: 443-48-1
• Molecular Weight: 171.15
• Beilstein: 611683
• EC Number: 207-136-1
• MDL number: MFCD00009750
• UNSPSC Code: 51282808
• PubChem Substance ID: 24896667
• NACRES: NA.76

Properties

• product line: BioXtra
• impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• ign. residue: ≤0.1%
• color: white to light yellow
• mp: 159-161 °C (lit.)
• solubility: acetic acid: 0.1 M, clear, colorless to yellow
• anion traces: chloride (Cl^-): ≤0.05%; sulfate (SO₄^2-): ≤0.05%
• cation traces: Al: ≤0.0005%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.01%; Pb: ≤0.001%; Zn: ≤0.0005%
• antibiotic activity spectrum: Gram-negative bacteria; parasites
• Mode of action: DNA synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: CC1=NC=C([N+]([O-])=O)N1CCO
• InChI: 1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
• InChI key: VAOCPAMSLUNLGC-UHFFFAOYSA-N

Description

General description

Chemical structure: imidazole

Application

Metronidazole is used to study DNA damage and repair and has been found to induce the gene transfer agent VSH-1 in Brachyspira hyodysenteriae. It is commonly used for treatment of periodontitis and is used in bioavailability studies.

Biochem/physiol Actions

Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. Reduced metronidazole covalently binds to DNA which disrupts its helical structure, induces DNA strand breaks and inhibits bacterial nucleic acid synthesis. Bacterial cell death results.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H340,H350,H373
• Precautionary Statements: P202 - P260 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 1B - Muta. 1B - STOT RE 2
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves