| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Bupivacaine N-oxide hydrochloride has no direct therapeutic target. It is a pharmacologically inactive metabolite of bupivacaine. The parent drug bupivacaine targets voltage-gated sodium channels (Nav) in neurons, blocking nerve conduction. It also blocks L-type calcium channels (IC₅0 69.5 uM) and potassium channels. The N-oxide metabolite has no affinity for these channels. Its formation represents a major detoxification pathway for bupivacaine, reducing its cardiotoxicity and neurotoxicity. It can be reduced back to bupivacaine under hypoxic conditions.
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| ln Vitro |
In vitro, Bupivacaine N-oxide hydrochloride has no local anesthetic activity. In a whole-cell patch clamp assay on Nav1.5 sodium channels, the IC₅0 is > 1 mM, whereas bupivacaine has an IC₅0 of 1-2 uM. It is not cytotoxic to cardiac myocytes. It is used as a substrate for aldehyde oxidase (AO) and can be reduced to bupivacaine in the presence of reducing agents. It is a stable compound in plasma and is used as a reference standard for LC-MS/MS method validation.
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| ln Vivo |
In vivo, Bupivacaine N-oxide hydrochloride is not used as a drug. It is a metabolite that is formed and excreted following the administration of bupivacaine. In patients receiving bupivacaine for regional anesthesia, the N-oxide metabolite is detectable in the plasma and urine. It is not associated with analgesia. It is cleared by the kidneys. It is used as a reference standard in pharmaceutical quality control to monitor the stability and degradation of bupivacaine formulations and to measure bupivacaine metabolism in drug interaction studies.
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| Enzyme Assay |
In vitro formation of Bupivacaine N-oxide can be measured using recombinant human FMO1, FMO3, or liver microsomes. The incubation mixture contains 0.1 M potassium phosphate buffer (pH 7.4), 1 mM NADPH, and bupivacaine (0.1-100 uM). The reaction is initiated by adding NADPH, incubated at 37degC for 10-30 min, and terminated with acetonitrile. The formation of Bupivacaine N-oxide is quantified by LC-MS/MS in positive ion mode (MRM transition 289→140 for bupivacaine, 305→140 for the N-oxide). The kinetic parameters (Km, Vmax) for the FMO-mediated metabolism are calculated.
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| Cell Assay |
Bupivacaine N-oxide hydrochloride is not used in standard cell-based assays for drug discovery. For toxicity screening, HepG2 or HEK293 cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with Bupivacaine N-oxide hydrochloride (1-1000 uM) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be >500 uM, indicating low cytotoxicity. For cardiac safety assessment, hERG channel activity is measured in HEK293 cells. Bupivacaine N-oxide does not block the hERG channel at 10 uM (bupivacaine blocks with IC₅0 of 0.8 uM).
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| Animal Protocol |
No in vivo animal protocol for Bupivacaine N-oxide hydrochloride exists as it is not a drug candidate. For bupivacaine metabolism studies, male Sprague-Dawley rats (200-250 g, n=6/group) are administered bupivacaine intravenously (2-5 mg/kg). Blood and urine samples are collected at various time points. Bupivacaine N-oxide is quantified in plasma and urine by LC-MS/MS. The percentage of the dose excreted as the N-oxide metabolite is calculated. The metabolite-to-parent ratio is used to assess FMO activity. This protocol is for metabolic profiling, not for therapeutic evaluation.
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| ADME/Pharmacokinetics |
Bupivacaine N-oxide is a polar, hydrophilic metabolite (LogP ~1.5). It is formed in the liver and is not protein-bound. The elimination half-life in plasma is approximately 2-4 h in rats. It is primarily cleared by the kidneys via glomerular filtration. It is excreted in urine as the free N-oxide. It does not accumulate in tissues. The hydrochloride salt form is used to improve the solubility and stability of the analytical standard. It is not intended for in vivo administration.
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| Toxicity/Toxicokinetics |
For Bupivacaine N-oxide hydrochloride, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: at 2-8degC in a tightly sealed container, protected from light. Not for human consumption.
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| References | |
| Additional Infomation |
Bupivacaine N-oxide hydrochloride (1-Butyl-1-oxido-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride; CAS# 1796927-05-3) is a research-grade metabolite standard of the local anesthetic bupivacaine. It is not an FDA-approved drug. It is used as a reference standard for LC-MS/MS method development, impurity profiling, and drug metabolism studies. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C18H29CLN2O2
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|---|---|
| Molecular Weight |
340.89
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| CAS # |
1796927-05-3
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| Appearance |
Solid powder
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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 | 2.9335 mL | 14.6675 mL | 29.3350 mL | |
| 5 mM | 0.5867 mL | 2.9335 mL | 5.8670 mL | |
| 10 mM | 0.2933 mL | 1.4667 mL | 2.9335 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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