| Size | Price | Stock | Qty |
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| 5g |
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| 10g |
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| Other Sizes |
| Targets |
Antibacterial, antimicrobial, antiparasitic, antitrichomonal
Metronidazole Benzoate targets the DNA of microbial cells. Upon hydrolysis to Metronidazole, the active drug enters microbial cells where it is reduced. This reduction generates toxic intermediates that disrupt the DNA of the cell, inhibiting nucleic acid synthesis and leading to cell death. This mechanism is effective against a wide range of anaerobic bacteria and protozoa. The benzoate esterification improves the drug's properties for specific formulations, such as a less bitter taste for oral suspensions. |
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| ln Vitro |
Many anaerobic, protozoan, and bacteroid bacterial infections, such as trichomoniasis, amebiasis, vaginosis, and gingivitis, can be treated with metronidazole benzoate[1].
In vitro studies have confirmed the broad-spectrum antimicrobial activity of Metronidazole Benzoate. Upon hydrolysis, it releases Metronidazole, which is effective against anaerobic bacteria and protozoa. It is indicated for the treatment of a wide range of infections, including trichomoniasis, amebiasis, vaginosis, and gingivitis. The compound's activity is a result of the disruption of microbial DNA synthesis. |
| ln Vivo |
Metronidazole Benzoate is used clinically as an antibiotic and antiprotozoal medication. Following oral administration, it is hydrolyzed to release active Metronidazole, which is then distributed throughout the body to treat systemic and local infections. It is effective in treating infections caused by anaerobic bacteria and certain parasites. The benzoate ester form is often used to mask the bitter taste of Metronidazole in pediatric and geriatric formulations.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays are not the primary mode of study for Metronidazole Benzoate, as its mechanism involves DNA disruption rather than receptor binding. However, its hydrolysis to Metronidazole can be studied using esterase enzymes in buffer solutions. The release of Metronidazole is measured by HPLC or LC-MS. The antimicrobial activity can be assessed using standard susceptibility tests (e.g., broth microdilution) against anaerobic bacterial cultures.
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| Cell Assay |
For in vitro cell-based assays, Metronidazole Benzoate is tested against anaerobic and protozoan cultures. The compound is added to culture media at various concentrations, and microbial growth is monitored by optical density or colony counting. The minimum inhibitory concentration (MIC) is determined. Its activity is compared to that of Metronidazole to confirm prodrug conversion and efficacy. The compound's cytotoxicity can be assessed in mammalian cell lines using MTT assays.
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| Animal Protocol |
In vivo animal studies with Metronidazole Benzoate are typically conducted in the context of efficacy testing against anaerobic or protozoal infections. Animal models of infection (e.g., rodent models of amebiasis or bacterial abscess) are used. The compound is administered orally, and its efficacy is measured by reduction in pathogen load, survival rates, or resolution of infection symptoms. Pharmacokinetic studies assess the rate and extent of conversion to Metronidazole.
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| ADME/Pharmacokinetics |
Metronidazole Benzoate (CAS: 13182-89-3) is a prodrug with a molecular weight of 275.26 g/mol and a molecular formula of C13H13N3O4. It is a solid at room temperature. Upon oral administration, it is hydrolyzed in the gastrointestinal tract to release the active drug, Metronidazole, which is then absorbed. The benzoate ester form is often used to improve the palatability of oral liquid formulations, especially for children.
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| Toxicity/Toxicokinetics |
Metronidazole Benzoate shares the toxicity profile of Metronidazole. Common side effects include gastrointestinal disturbances, headache, and a metallic taste. More serious but rare side effects include neurological effects and disulfiram-like reactions with alcohol. The compound is contraindicated in the first trimester of pregnancy and in patients with a history of hypersensitivity to nitroimidazoles. It should be used with caution in patients with hepatic impairment.
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| References | |
| Additional Infomation |
Metronidazole benzoate is a benzoate formed by the condensation of benzoic acid and the hydroxyl group of metronidazole. It possesses antibacterial, antimicrobial, antiparasitic, antitrichomonal, and prodrug activities. Its functions are related to those of metronidazole and benzoic acid. Metronidazole benzoate is the benzoate of metronidazole, a synthetic nitroimidazole derivative with antiseptic and antibacterial activities. See also: Metronidazole (containing the active moiety).
Metronidazole Benzoate is a prodrug of the nitroimidazole antibiotic Metronidazole. It is used as an antibacterial, antimicrobial, antiparasitic, and antitrichomonal agent. By inhibiting nucleic acid synthesis, it disrupts the DNA of microbial cells. The benzoate ester is used to mask the bitter taste of the active drug in oral suspensions. It is available as a pharmaceutical ingredient and is not just a research chemical. |
| Molecular Formula |
C13H13N3O4
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|---|---|
| Molecular Weight |
275.26002
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| Exact Mass |
194.057
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| Elemental Analysis |
C, 56.72; H, 4.76; N, 15.27; O, 23.25
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| CAS # |
13182-89-3
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| Related CAS # |
69198-10-3 (HCl);13182-82-6 (acetate);13182-89-3 (benzoate);443-48-1; 1460293-84-8 (sodium);
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| PubChem CID |
83213
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| Appearance |
Solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
372.3±27.0 °C at 760 mmHg
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| Melting Point |
102 °C
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| Flash Point |
150.5±17.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.627
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| LogP |
1.64
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
352
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(OCCN1C([N+]([O-])=O)=CN=C1C)C2=CC=CC=C2
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| InChi Key |
CUUCCLJJOWSASK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H13N3O4/c1-10-14-9-12(16(18)19)15(10)7-8-20-13(17)11-5-3-2-4-6-11/h2-6,9H,7-8H2,1H3
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| Chemical Name |
2-(2-Methyl-5-nitroimidazol-1-yl)ethyl benzoate
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| Synonyms |
Benzoylmetronidazole; Metronidazole benzoate
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~908.23 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.56 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 (7.56 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.56 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6329 mL | 18.1646 mL | 36.3293 mL | |
| 5 mM | 0.7266 mL | 3.6329 mL | 7.2659 mL | |
| 10 mM | 0.3633 mL | 1.8165 mL | 3.6329 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.
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.
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