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M1547 Sigma-Aldrich

Metronidazole

BioXtra

Synonym: 2-Methyl-5-nitroimidazole-1-ethanol

  • CAS Number 443-48-1

  • Empirical Formula (Hill Notation) C6H9N3O3

  • Molecular Weight 171.15

  •  Beilstein/REAXYS Number 611683

  •  EC Number 207-136-1

  •  MDL number MFCD00009750

  •  PubChem Substance ID 24896667

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application,
Quality Level   200
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 (SO42-): ≤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%
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   Gram-negative bacteria
  parasites
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 a nitroimidazole used to treat amebiasis, vaginitis, Trichomonas infections, giardiasis, anaerobic bacteria and treponemal infections. 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.

Packaging

5, 25 g in glass bottle

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 & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NI5600000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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