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Merck

M1547

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
UNSPSC Code:
51282808
NACRES:
NA.76
PubChem Substance ID:
24896667
EC Number:
207-136-1
Beilstein/REAXYS Number:
611683
MDL number:
MFCD00009750

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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

SMILES string

CC1=NC=C([N+]([O-])=O)N1CCO

product line

BioXtra

impurities

≤0.2% Total Impurities

ign. residue

≤0.1%

color

white to light yellow

Quality Level

200

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

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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.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Carc. 1B - Muta. 1B - STOT RE 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

M1547-BULK: + M1547-25G: + M1547-VAR: + M1547-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
0000512471
0000512480
0000490355
0000490355
0000485816

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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
Xi Lin et al.
Cell reports, 33(1), 108227-108227 (2020-10-08)
Immune cells in the mucosal barriers of vertebrates are highly heterogeneous in their origin and function. This heterogeneity is further exemplified by the recent discovery of ectoderm-derived immune cells-metaphocytes in zebrafish epidermis. Yet, whether non-hematopoiesis-derived immune cells generally exist in
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.
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