| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Bacterial and protozoal DNA. Hydroxymetronidazole, like its parent drug metronidazole, is a nitroimidazole compound that exerts its antimicrobial activity after reductive activation by bacterial/parasite nitroreductases. The reduced form generates toxic radicals that damage DNA, leading to cell death. It is an active metabolite with antimicrobial activity against anaerobic bacteria and protozoa.
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| ln Vitro |
Hydroxymetronidazole is active against anaerobic bacteria, including Bacteroides fragilis (MIC = 1 ug/mL), B. thetaiotaomicron (MIC = 2 ug/mL), B. distasonis (MIC = 1 ug/mL), and B. ovatus (MIC = 2 ug/mL). It is the major human urinary metabolite of metronidazole and is active against the same spectrum of anaerobic organisms as the parent drug, though its potency is generally lower than metronidazole.
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| ln Vivo |
No specific in vivo data has been reported for Hydroxymetronidazole. As an active metabolite of metronidazole, it contributes to the overall efficacy of metronidazole therapy. In vivo, it is formed in the liver and excreted in the urine. Metronidazole (and its metabolites) are used to treat infections caused by susceptible anaerobic bacteria (e.g., intra-abdominal, gynecologic, and dental infections) and protozoal infections (e.g., giardiasis, amebiasis).
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| Enzyme Assay |
Not applicable. Hydroxymetronidazole is a metabolite of metronidazole, and its antimicrobial activity is not typically studied in cell-free enzyme binding assays. For drug metabolism studies, human liver microsomes (HLMs) or recombinant CYP enzymes (e.g., CYP2A6) are incubated with metronidazole (1-100 uM) and NADPH (1 mM) in phosphate buffer (pH 7.4) at 37degC for 30-60 minutes. The reaction is stopped by adding acetonitrile, and Hydroxymetronidazole formation is quantified by LC-MS/MS. The metabolite is identified by comparison with a reference standard. For nitroreductase assays, bacterial nitroreductase enzymes are incubated with the compound in anaerobic conditions, and the reduction product is monitored by spectrophotometry.
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| Cell Assay |
Hydroxymetronidazole is used as an analytical standard for quantifying metronidazole and its metabolites in biological samples, not as a test article in cell culture. For cytotoxicity or antimicrobial assays, anaerobic bacteria (e.g., B. fragilis) are cultured in pre-reduced Brucella broth supplemented with hemin and vitamin K. Bacteria are inoculated into 96-well plates at 10⁵-10⁶ CFU/well. Hydroxymetronidazole is serially diluted (0.01-100 ug/mL) and added to wells. Plates are incubated in an anaerobic chamber (85% N2, 10% H2, 5% CO2) at 37degC for 48 hours. MIC is determined as the lowest concentration that inhibits visible growth. The MIC values against B. fragilis have been reported as 1-2 ug/mL.
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| Animal Protocol |
No specific animal studies are conducted with Hydroxymetronidazole alone, as it is a metabolite. In a typical metronidazole PK study, male Sprague-Dawley rats (200-250 g) are administered metronidazole (50 mg/kg) via oral gavage or intravenous injection. Blood samples are collected at 0, 0.5, 1, 2, 4, 6, 8, 12, 24 hours post-dose. Plasma is separated, and Hydroxymetronidazole (along with metronidazole and other metabolites) is quantified by LC-MS/MS. Urine is collected over 24-48 hours using metabolic cages to determine cumulative excretion of the metabolite. The metabolite accounts for approximately 30-60% of the administered dose in urine.
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| ADME/Pharmacokinetics |
Hydroxymetronidazole has a molecular weight of 187.15 g/mol. In humans, it is a major urinary metabolite of metronidazole, and its formation is primarily catalyzed by CYP2A6. The metabolite is formed in the liver and excreted in urine, with a half-life similar to metronidazole (approximately 6-10 hours). It is less lipophilic than metronidazole (XLogP3 = -1.3 vs. metronidazole -0.1), resulting in reduced tissue penetration. The plasma protein binding is low.
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| Toxicity/Toxicokinetics |
No specific toxicity data is reported for Hydroxymetronidazole. As a metabolite of metronidazole, it shares the same toxicity profile as the parent drug. Metronidazole is generally well tolerated but can cause nausea, headache, metallic taste, and neurological effects (dizziness, peripheral neuropathy with prolonged use). It has a disulfiram-like reaction with alcohol. It is not recommended for use in pregnancy or lactation. Hydroxymetronidazole is for research and analytical use only.
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| References |
[1]. Rodrigo H M M Granja, et al. Determination and confirmation of metronidazole, dimetridazole, ronidazole and their metabolites in bovine muscle by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(6):970-6.
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| Additional Infomation |
Metronidazole-OH belongs to the imidazole class of compounds and is a C-nitro compound.
Hydroxymetronidazole is also known as 1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole and 2-(hydroxymethyl)-5-nitro-1H-imidazole-1-ethanol. The molecular formula is C6H9N3O4, and the molecular weight is 187.15. It is used as an analytical reference standard for the quantification of metronidazole and its metabolites in biological samples by LC-MS/MS. It is a controlled substance for research use only, not for human consumption. It is stored at 2-8degC as a solid. |
| Molecular Formula |
C6H9N3O4
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|---|---|
| Molecular Weight |
187.15
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| Exact Mass |
187.059
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| CAS # |
4812-40-2
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| Related CAS # |
Hydroxymetronidazole-d4;1215071-08-1
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| PubChem CID |
121858
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.61g/cm3
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| Boiling Point |
475.2ºC at 760mmHg
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| Melting Point |
118-121ºC
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| Flash Point |
241.2ºC
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| Index of Refraction |
1.643
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| LogP |
-1.3
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
183
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(CO)N1C(=NC=C1[N+](=O)[O-])CO
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| InChi Key |
AEHPOYAOLCAMIU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H9N3O4/c10-2-1-8-5(4-11)7-3-6(8)9(12)13/h3,10-11H,1-2,4H2
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| Chemical Name |
2-[2-(hydroxymethyl)-5-nitroimidazol-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 | 5.3433 mL | 26.7165 mL | 53.4331 mL | |
| 5 mM | 1.0687 mL | 5.3433 mL | 10.6866 mL | |
| 10 mM | 0.5343 mL | 2.6717 mL | 5.3433 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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