Metronidazole

Alias:
Cat No.:V1480 Purity: ≥98%
Metronidazole (trade names Flagyl, Metro, Trichopol, Vagilen), an imidazole-based and synthetic antibacterial and antiprotozoal drug belonging to the nitroimidazole class, is commonly used for the treatment of protozoa and other baterial infections.
Metronidazole Chemical Structure CAS No.: 443-48-1
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
10g
50g
100g
Other Sizes

Other Forms of Metronidazole:

  • Metronidazole Benzoate
  • Metronidazole HCl
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Metronidazole (trade names Flagyl, Metro, Trichopol, Vagilen), an imidazole-based and synthetic antibacterial and antiprotozoal drug belonging to the nitroimidazole class, is commonly used for the treatment of protozoa and other baterial infections.For the treatment of a variety of infections, including endocarditis, bacterial vaginosis, and pelvic inflammatory disease, metronidazole can be used either on its own or in combination with other antibiotics. Additionally, it works well for amebiasis, trichomoniasis, giardiasis, and dracunculiasis.

Biological Activity I Assay Protocols (From Reference)
Targets
DNA synthesis
ln Vitro

Metronidazole is largely dormant until it is broken down by microbial or host cells. When ferredoxin or fla vodoxin, which is reduced by POR in anaerobic or microaerophilic bacteria or luminal parasites, transfers an electron to metronidazole, the drug becomes active. Metronidazole causes cellular damage by forming adducts of DNA and proteins.[1] Metronidazole was first licensed as a useful treatment for the protozoan infections Entamoeba histolytica, Giardia lamblia, and Trichomonas vaginalis. Metronidazole's ability to inhibit anaerobic gut flora has been utilized to treat and prevent infectious complications in Crohn's disease patients. Metronidazole has been a significant factor in infections linked to anaerobic conditions. Treating anaerobic brain abscesses with metronidazole has proven to be remarkably successful.[2] Instead of being caused by the lateral transfer of mutant rdxA (or other) genes from unrelated but Mtzr strains, metronidazole resistance typically results from a de novo mutation in the resident rdxA gene. In rdxA(+) (metronidazole(s)) and rdxA (metronidazole(r)) H. pylori strains, metronidazole partially inhibits growth and stimulates forward mutation to rifampin resistance. Moreover, in Escherichia coli, rdxA expression causes an equivalent Mtz-induced mutation.[3] In growing cultures of axenic B. hominis, metronidazole induces apoptosis-like features, including important morphological and biochemical characteristics of programmed cell death (PCD), such as nuclear condensation and nicked DNA in the nucleus, decreased cytoplasmic volume, externalization of phosphatidylserine, and preservation of plasma membrane integrity with increasing permeability.[4]

ln Vivo
Metronidazole (135 mg/kg/d; p.o.; 28 d) can penetrate the blood-brain barrier and, when given to rats over an extended period of time, show neurotoxicity[3].
Metronidazole (1 g/L; p.o.; 4 weeks) causes atrophy in skeletal muscle and alters the expression of genes related to metabolic regulation and the peripheral circadian rhythm machinery of the muscle[4].
Cell Assay
Cell Line: Blastocystis sp. Cells
Concentration: 0.1 μg/mL-0.01 mg/mL
Incubation Time: 12, 24, 48, 60, 72, 84, 96 hours
Result: Decreased cell diameter, as a hallmark of an apoptotic cell, and resulted cell shrinkage.
Animal Protocol
Sprague-Dawley (SD) rats (200-220 g)
135 mg/kg
Oral gavage; once daily; 28 days
References

[1]. Antimicrob Agents Chemother . 1999 Jul;43(7):1533-41.

[2]. Drugs . 1991 Sep;42(3):428-67.

[3]. J Bacteriol . 2000 Sep;182(18):5091-6.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H9N3O3
Molecular Weight
171.15
Exact Mass
171.06
Elemental Analysis
C, 42.10; H, 5.30; N, 24.55; O, 28.04
CAS #
443-48-1
Related CAS #
1460293-84-8 (sodium); 13182-82-6 (acetate); 443-48-1 (free); 13182-89-3 (benzoate); 69198-10-3 (HCl); 443-48-1
Appearance
White to light yellow crystalline powder
SMILES
CC1=NC=C(N1CCO)[N+](=O)[O-]
InChi Key
VAOCPAMSLUNLGC-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
Chemical Name
2-(2-methyl-5-nitroimidazol-1-yl)ethanol
Synonyms

Metro; Flagyl; Trichopol; Vagilen; Metronidazole

HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 34~35 mg/mL (198.7~204.5 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (12.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (12.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (12.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 12.5 mg/mL (73.04 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.8428 mL 29.2141 mL 58.4283 mL
5 mM 1.1686 mL 5.8428 mL 11.6857 mL
10 mM 0.5843 mL 2.9214 mL 5.8428 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04478617 Active
Recruiting
Drug: Metronidazole Vaginal Post-Op Infection New York Medical College July 15, 2020 Phase 4
NCT01521403 Active
Recruiting
Drug: Metronidazole
Drug: Placebo
Blastocystis Hominis Infections University of Lausanne Hospitals November 2012 Phase 4
NCT04827537 Active
Recruiting
Drug: Metronidazole Oral
Drug: Placebo Oral
Giardia Lamblia Infection Research Institute of
Epidemiology, Microbiology
and Infectious Diseases,
Uzbekistan
January 1, 2021 Phase 1
Phase 2
NCT05748145 Recruiting Drug: Metronidazole Oral Colorectal Cancer Oncology Institute of Southern
Switzerland
September 11, 2023 Phase 2
NCT04554693 Recruiting Drug: Metronidazole Oral
Drug: Placebo
Endometriosis-related Pain
Endometriosis
University of Louisville October 19, 2020 Phase 4
Biological Data
  • Diverse locations of metronidazole-sensitive eukaryotic organisms in a phylogenetic tree constructed by using small ssRNA sequences. Antimicrob Agents Chemother . 1999 Jul;43(7):1533-41.
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