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M1547

Sigma-Aldrich

Metronidazole

BioXtra

Synonym(s):

2-Methyl-5-nitroimidazole-1-ethanol

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About This Item

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

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%

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

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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.

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Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H350,H373

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

Certificates of Analysis (COA)

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Tal Frolinger et al.
Scientific reports, 9(1), 3546-3546 (2019-03-07)
Dietary polyphenols promote memory in models of sleep deprivation (SD), stress, and neurodegeneration. The biological properties of dietary polyphenols greatly depend upon the bioavailability of their phenolic metabolites derivatives, which are modulated by gut microbiota. We recently demonstrated that supplementation
Fabrizio Palumbo et al.
Cell reports, 32(8), 108054-108054 (2020-08-28)
Operant learning requires multiple cognitive processes, such as learning, prediction of potential outcomes, and decision-making. It is less clear how interactions of these processes lead to the behavioral adaptations that allow animals to cope with a changing environment. We show
D Nyasha Chagwedera et al.
Cell metabolism, 30(2), 364-373 (2019-05-28)
Microbial dysbiosis and inflammation are implicated in diet-induced obesity and insulin resistance. However, it is not known whether crosstalk between immunity and microbiota also regulates metabolic homeostasis in healthy animals. Here, we report that genetic deletion of tuberous sclerosis 1
Sonja Löfmark et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 50 Suppl 1, S16-S23 (2010-01-14)
Metronidazole has been used for the treatment of infections for >45 years and is still successfully used for the treatment of trichomoniasis, amoebiasis, and giardiasis. Anaerobic bacterial infections caused by Bacteroides species, fusobacteria, and clostridia respond favorably to metronidazole therapy.
Manoj K Puthia et al.
Eukaryotic cell, 7(3), 435-443 (2007-12-25)
Blastocystis is a ubiquitous enteric protozoan found in the intestinal tracts of humans and a wide range of animals. Evidence accumulated over the last decade suggests association of Blastocystis with gastrointestinal disorders involving diarrhea, abdominal pain, constipation, nausea, and fatigue.
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