| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Target: Bacterial and Protozoal DNA. Metronidazole is a prodrug that is activated by reduction of its nitro group by nitroreductases in anaerobic bacteria and protozoa. The reduced form generates toxic reactive intermediates that bind to DNA and other macromolecules, causing strand breakage, inhibition of nucleic acid synthesis, and cell death. It is active against anaerobic bacteria (Bacteroides, Clostridium, Fusobacterium) and protozoa (Trichomonas vaginalis, Giardia lamblia, Entamoeba histolytica). The labeled version is an analytical standard.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, the labeled standard has no direct biological activity. The unlabeled metronidazole (0.1-100 ug/mL) exhibits bactericidal and protozoacidal activity against anaerobic microorganisms, with MIC values typically in the range of 0.125-8 ug/mL. It is more active under anaerobic conditions due to the reductive activation mechanism. The compound is also used in H. pylori eradication regimens (as a part of triple or quadruple therapy) for peptic ulcer disease. |
| ln Vivo |
In vivo, the unlabeled metronidazole is used clinically for the treatment of various anaerobic bacterial infections (e.g., intra-abdominal infections, pelvic inflammatory disease, bacterial vaginosis, Clostridium difficile infection, aspiration pneumonia) and protozoal infections (e.g., trichomoniasis, giardiasis, amebiasis). It is also used in combination with other antibiotics for Helicobacter pylori eradication and for the treatment of rosacea (topical formulation). The labeled standard is not administered in vivo; it is used as an internal standard for PK studies of metronidazole.
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| Enzyme Assay |
For cell-free assays (LC-MS/MS): plasma, serum, urine, or tissue homogenates are spiked with Metronidazole-d3 internal standard. After protein precipitation with acetonitrile or methanol, and centrifugation, the supernatant is injected into an LC-MS/MS system equipped with a C18 reverse-phase column. Detection is typically performed in positive ion mode ESI-MS/MS using multiple reaction monitoring (MRM). Quantitation is based on the analyte/internal standard peak area ratio. Isotope dilution mass spectrometry is used to correct for matrix effects and ensure accurate quantification of metronidazole and its major metabolites (e.g., hydroxy-metronidazole). The deuterated standard co-elutes with the unlabeled analyte, providing an internal standard with identical extraction recovery and ionization efficiency.
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| Cell Assay |
No cell-based assays are performed with the deuterated standard. The unlabeled metronidazole is tested in antimicrobial susceptibility assays using broth microdilution or agar dilution methods according to CLSI guidelines. Minimum inhibitory concentrations (MICs) are determined for anaerobic bacterial reference strains (e.g., B. fragilis, C. perfringens) and for protozoal cultures (e.g., T. vaginalis, G. lamblia). The labeled standard is not used in these assays.
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| Animal Protocol |
No animal studies are conducted with the labeled internal standard itself. For PK studies of metronidazole, animals (rats, dogs, or mice) are administered the drug orally, intravenously, or intraperitoneally. Serial blood samples are collected, plasma is processed, and the deuterated internal standard is used in LC-MS/MS bioanalysis to determine metronidazole concentrations. PK parameters (Cmax, Tmax, t1/2, AUC, volume of distribution, clearance, oral bioavailability) are calculated. The standard is also used in tissue distribution and metabolism studies to measure metronidazole and its metabolites in various organs and in cerebrospinal fluid (CSF).
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| ADME/Pharmacokinetics |
PK properties of metronidazole: After oral administration, it is rapidly and almost completely absorbed (oral bioavailability >90%). Tmax is 1-2 h. Plasma protein binding is low (<20%). It is widely distributed to tissues, including the CNS (CSF concentrations are similar to plasma), and crosses the placenta and enters breast milk. It is extensively metabolized in the liver by CYP450 enzymes (primarily CYP2A6, CYP2B6, CYP2C9, CYP2C19, and CYP3A4) to its major metabolites: hydroxy-metronidazole (active, ~30% of parent activity) and acetic acid metabolites. The terminal elimination half-life is approximately 6-8 h (up to 18-20 h in patients with hepatic impairment). Approximately 60-80% of a dose is excreted in urine (primarily as metabolites and unchanged drug), with 6-15% excreted in feces. The deuterated standard co-elutes with the analyte, ensuring accurate PK parameter determination.
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| Toxicity/Toxicokinetics |
No toxicity data are reported for the deuterated standard. The unlabeled metronidazole has a well-characterized safety profile: common adverse effects (5-15%) include metallic taste in mouth (most common), nausea, vomiting, diarrhea, anorexia, headache, dizziness, and darkening of urine (due to metabolites). Serious but rare adverse effects include peripheral neuropathy (usually with prolonged high-dose use), CNS toxicity (seizures, encephalopathy, ataxia), and disulfiram-like reaction (if taken with alcohol, causing nausea, vomiting, flushing, tachycardia). Metronidazole is a potential human carcinogen (has been shown to be carcinogenic in mice and rats at high doses). It should be used with caution in patients with hepatic impairment. The labeled compound is for research use only and is not intended for human therapeutic administration. It is non-hazardous for transport under normal laboratory conditions but should be handled with appropriate safety precautions due to its carcinogenic potential.
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| References | |
| Additional Infomation |
Metronidazole-d3 is a research standard and is not an active drug substance. The unlabeled metronidazole (Flagyl, Metrogel) is FDA-approved for the treatment of anaerobic bacterial infections, trichomoniasis, giardiasis, amebiasis, bacterial vaginosis, and as part of H. pylori eradication therapy. It is also approved for the treatment of rosacea (topical gel). The deuterated standard is used for analytical method development, method validation (AMV), quality control (QC), and abbreviated new drug application (ANDA) submissions for metronidazole-containing pharmaceutical products (oral tablets/capsules, IV infusion, topical gels/creams, vaginal preparations). It is essential for therapeutic drug monitoring (TDM) in patients receiving high-dose or prolonged metronidazole therapy (e.g., anaerobic infections, IBD) and for clinical PK studies, bioequivalence studies, and environmental monitoring (wastewater analysis of pharmaceutical residues).
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| Molecular Formula |
C5H4CLIN2
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| Molecular Weight |
254.45613193512
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| Exact Mass |
174.083
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| CAS # |
83413-09-6
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| Related CAS # |
Metronidazole;443-48-1
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| PubChem CID |
21788197
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| Appearance |
Light yellow to yellow solid powder
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| LogP |
0.615
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
170
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C([2H])([2H])C1=NC=C(N1CCO)[N+](=O)[O-]
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| InChi Key |
VAOCPAMSLUNLGC-FIBGUPNXSA-N
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| InChi Code |
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3/i1D3
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| Chemical Name |
2-[5-nitro-2-(trideuteriomethyl)imidazol-1-yl]ethanol
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9299 mL | 19.6495 mL | 39.2989 mL | |
| 5 mM | 0.7860 mL | 3.9299 mL | 7.8598 mL | |
| 10 mM | 0.3930 mL | 1.9649 mL | 3.9299 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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