Metronidazole
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| Category | Antibiotics |
| Catalog number | BBF-04552 |
| CAS | 443-48-1 |
| Molecular Weight | 171.15 |
| Molecular Formula | C6H9N3O3 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04552 | 500 g | $439 | In stock |
Online Inquiry
Add to cartDescription
Metronidazole is a synthetic antibacterial and antiprotozoal agent of the nitroimidazole class. It is a limited spectrum antibiotic that has activity against anaerobic gram-positive and anaerobic gram-negative bacteria. It is also promisingly to be a radiation sensitizer for hypoxic cells.
Specification
| Related CAS | 69198-10-3 (mono-hydrochloride) |
| Synonyms | Flagyl; Metronidazol; 2-Methyl-5-nitroimidazole-1-Ethanol; Novonidazol; 2-Methyl-5-nitro-1H-imidazole-1-Ethanol; Anagiardil; Arilin; Bayer 5360; Cimetrol 500LPCI; Clont; Deflamon; Dentamet gel; Efloran; Elyzol; Flagesol; Flagil; 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole; NSC 50364; NSC 69587; Nidazole |
| Storage | Store at 2-8°C |
| IUPAC Name | 2-(2-methyl-5-nitroimidazol-1-yl)Ethanol |
| Canonical SMILES | CC1=NC=C(N1CCO)[N+](=O)[O-] |
| InChI | 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 |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Parasites |
| Boiling Point | 405.4°C at 760 mmHg |
| Melting Point | 156-158°C |
| Density | 1.45 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol |
| LogP | -0.02 |
Toxicity
| Carcinogenicity | 2B, possibly carcinogenic to humans. |
| Mechanism Of Toxicity | Metronidazole is a prodrug. Unionized metronidazole is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. This reduced metronidazole then covalently binds to DNA, disrupt its helical structure, inhibiting bacterial nucleic acid synthesis and resulting in bacterial cell death. |
| Toxicity | LD50 = 500 mg/kg/day (orally in rat). |
Reference Reading
1.Antibiotic resistance and CYP2C19 polymorphisms affect the efficacy of concomitant therapies for Helicobacter pylori infection: an open-label, randomized, single-centre clinical trial.
Hong J1, Shu X1, Liu D2, Zhu Y1, Xie C2, Xie Y2, Zhang K2, Wang A1, Xiong H1, Zeng H3, Yu H3, Ma J4, Chen Y4, Zhu X1, Lu N5. J Antimicrob Chemother. 2016 Apr 21. pii: dkw118. [Epub ahead of print]
OBJECTIVES: We evaluate the efficacy of concomitant therapy for Helicobacter pylori infection and the associated factors that influence it in China, where it has not previously been investigated.
2.Water Sources in a Zoological Park Harbor Genetically Diverse Strains of Clostridium Perfringens Type A with Decreased Susceptibility to Metronidazole.
Álvarez-Pérez S1, Blanco JL2,3, Peláez T4,5, Martínez-Nevado E6, García ME1. Microb Ecol. 2016 Apr 26. [Epub ahead of print]
The presence of Clostridium perfringens in water is generally regarded as an indicator of fecal contamination, and exposure to waterborne spores is considered a possible source of infection for animals. We assessed the presence and genetic diversity of C. perfringens in water sources in a zoological park located in Madrid (Spain). A total of 48 water samples from 24 different sources were analyzed, and recovered isolates were toxinotyped, genotyped by fluorophore-enhanced repetitive polymerase chain reaction (rep-PCR) fingerprinting and tested for antimicrobial susceptibility. C. perfringens was recovered from 43.8 % of water samples and 50 % of water sources analyzed. All isolates (n = 70) were type A and 42.9 % were β2-toxigenic (i.e., cpb2+), but none contained the enterotoxin-encoding gene (cpe). Isolates belonged to 15 rep-PCR genotypes and most genetic diversity (88 %) was distributed among isolates obtained from the same sample. Most isolates displayed intermediate susceptibility (57.
3.Characterization of Antimicrobial Agent Loaded Eudragit RS Solvent Exchange-Induced In Situ Forming Gels for Periodontitis Treatment.
Phaechamud T1, Jantadee T2, Mahadlek J3, Charoensuksai P4, Pichayakorn W5. AAPS PharmSciTech. 2016 Apr 26. [Epub ahead of print]
Eudragit RS (ERS), a quaternary polyacrylate positively charged polymer, exhibits a very low permeability and swells in aqueous media independently of pH without dissolving. Owing to its high solubility in N-methyl pyrrolidone (NMP), it was interesting to apply as polymer matrix for solvent-exchanged in situ forming gel. The aim of this research was to prepare in situ forming gels from ERS to deliver the antimicrobial agents (doxycycline hyclate, metronidazole, and benzoyl peroxide) for periodontitis treatment. They were evaluated for viscosity and rheology, gel formation, syringeability, drug release, and antimicrobial activities. The solvent exchange between NMP and an external aqueous simulated gingival crevicular fluid stimulated the dissolved ERS transforming into the opaque rigid gel. Antimicrobial agent loaded ERS systems exhibited Newtonian flow with acceptable syringeability. The higher-loaded ERS promoted the more prolongation of drug release because of the retardation of water diffusion into the precipitated matrix.
4.A novel method for imaging the pharmacological effects of antibiotic treatment on Clostridium difficile.
Endres BT1, Bassères E1, Memariani A2, Chang L3, Alam MJ1, Vickers RJ4, Kakadiaris IA2, Garey KW5. Anaerobe. 2016 Apr 20. pii: S1075-9964(16)30040-3. doi: 10.1016/j.anaerobe.2016.04.013. [Epub ahead of print]
Clostridium difficile is a significant cause of nosocomial-acquired infection that results in severe diarrhea and can lead to mortality. Treatment options for C. difficile infection (CDI) are limited, however, new antibiotics are being developed. Current methods for determining efficacy of experimental antibiotics on C. difficile involve antibiotic killing rates and do not give insight into the drug's pharmacologic effects. Considering this, we hypothesized that by using scanning electron microscopy (SEM) in tandem to drug killing curves, we would be able to determine efficacy and visualize the phenotypic response to drug treatment. To test this hypothesis, supraMIC kill curves were conducted using vancomycin, metronidazole, fidaxomicin, and ridinilazole. Following collection, cells were either plated or imaged using a scanning electron microscope (SEM). Consistent with previous reports, we found that the tested antibiotics had significant bactericidal activity at supraMIC concentrations.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C6H9N3O3
Molecular Weight (Monoisotopic Mass): 171.0644 Da
Molecular Weight (Avergae Mass): 171.154 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C6H9N3O3
Molecular Weight (Monoisotopic Mass): 171.0644 Da
Molecular Weight (Avergae Mass): 171.154 Da
LC-MS/MS Spectrum - LC-ESI-QTOF , positive
Experimental Conditions
Instrument Type: LC-ESI-QTOF
Ionization Mode: positive
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C6H9N3O3
Molecular Weight (Monoisotopic Mass): 171.0644 Da
Molecular Weight (Avergae Mass): 171.154 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C6H9N3O3
Molecular Weight (Monoisotopic Mass): 171.0644 Da
Molecular Weight (Avergae Mass): 171.154 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: DMSO-d6
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
