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M1547

Sigma-Aldrich

Metronidazole

BioXtra

Synonyme(s) :

2-Methyl-5-nitroimidazole-1-ethanol

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About This Item

Formule empirique (notation de Hill):
C6H9N3O3
Numéro CAS:
443-48-1
Poids moléculaire :
171.15
Numéro Beilstein :
611683
Numéro CE :
207-136-1
Numéro MDL:
MFCD00009750
Code UNSPSC :
51282808
ID de substance PubChem :
24896667
Nomenclature NACRES :
NA.76

Gamme de produits

BioXtra

Impuretés

≤0.2% Total Impurities

Résidus de calcination

≤0.1%

Couleur

white to light yellow

Pf

159-161 °C (lit.)

Solubilité

acetic acid: 0.1 M, clear, colorless to yellow

Traces d'anions

chloride (Cl-): ≤0.05%
sulfate (SO42-): ≤0.05%

Traces de cations

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%

Spectre d'activité de l'antibiotique

Gram-negative bacteria
parasites

Mode d’action

DNA synthesis | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

VAOCPAMSLUNLGC-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

907197

1,4-Dinitro-1-imidazole

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H340,H350,H373

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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.
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
Konstantinos Z Vardakas et al.
International journal of antimicrobial agents, 40(1), 1-8 (2012-03-09)
The objective of this review was to evaluate the frequency of treatment failure and recurrence of Clostridium difficile infection (CDI) following treatment with vancomycin or metronidazole in recently performed studies (last 10 years). Searches in PubMed and Scopus were performed
T H I Brummer et al.
BJOG : an international journal of obstetrics and gynaecology, 120(10), 1269-1276 (2013-06-22)
To evaluate cefuroxime and metronidazole antibiotic prophylaxis. Observational nonrandomised 1-year prospective cohort study. Fifty-three hospitals in Finland. A total of 5279 women undergoing hysterectomy for benign indications, with cefuroxime given to 4301 and metronidazole given to 2855. Excluding other antibiotics
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