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| Targets |
Carbamazepine 10,11 epoxide (the non-deuterated parent compound) primarily targets voltage-gated sodium channels (Nav channels) in neurons, stabilizing their inactive state and preventing repetitive neuronal firing. This action underlies the anticonvulsant and antiepileptic effects of the parent drug carbamazepine. The epoxide metabolite retains significant pharmacological activity, potentially contributing to both therapeutic efficacy and toxicity. It also binds to and inhibits various ion channels and neurotransmitter receptors, including GABA receptors and calcium channels. The deuterated version (d10) shares the same target but is used exclusively as an internal 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].
Carbamazepine 10,11 epoxide-d10 is not used for in vitro activity studies; it serves exclusively as an analytical internal standard. The non-deuterated parent metabolite, carbamazepine-10,11-epoxide, has been studied in vitro as an inhibitor of voltage-gated sodium channels, similar to its parent drug. It is also used as a substrate in metabolic studies to evaluate the activity of epoxide hydrolase enzymes, which convert the epoxide to its corresponding dihydrodiol metabolite. The deuterated version is not used in such activity assays; its sole purpose is analytical quantification. |
| ln Vivo |
Carbamazepine 10,11 epoxide (non-deuterated) is an active metabolite of carbamazepine formed in vivo by cytochrome P450 enzymes (primarily CYP3A4). The epoxide metabolite contributes to the anticonvulsant activity of carbamazepine but has also been implicated in some adverse effects, including idiosyncratic toxicity. Monitoring of carbamazepine-10,11-epoxide levels is important in clinical pharmacology for therapeutic drug monitoring (TDM) in patients treated with carbamazepine, particularly in cases of drug interactions or suspected toxicity. The deuterated version (d10) is used as an internal standard in these clinical assays.
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| Enzyme Assay |
For non-cellular assays (analytical quantification), Carbamazepine 10,11 epoxide-d10 is prepared as a stock solution in methanol or acetonitrile (1 mg/mL). For LC-MS/MS analysis, a calibration curve for carbamazepine-10,11-epoxide is prepared in human plasma or serum (0.1-1000 ng/mL) with a fixed concentration of the deuterated internal standard (e.g., 10-50 ng/mL). Sample preparation: 500 uL plasma + 50 uL internal standard + 1.5 mL acetonitrile for protein precipitation. After centrifugation, the supernatant is evaporated to dryness, reconstituted in 200 uL mobile phase (0.1% formic acid in water and acetonitrile, 60:40, v/v), and injected onto a C18 column (2.1×50 mm, 1.8 um). MRM transitions: carbamazepine-10,11-epoxide 253→180 (or 253→210), and for d10-labeled 263→190.
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| Cell Assay |
For cell-based assays, hepatocytes (primary human hepatocytes or HepG2 cells) are cultured in 6-well plates (1×10⁶ cells/well) in William‘s E medium with 10% FBS. Cells are treated with carbamazepine (10-100 uM) for 0-48 hours. Carbamazepine-10,11-epoxide levels in cell lysates and culture medium are measured by LC-MS/MS using carbamazepine 10,11 epoxide-d10 as internal standard. For epoxide hydrolase activity assays, microsomes or cell lysates are incubated with carbamazepine-10,11-epoxide (1-10 uM) for 30 minutes, and the dihydrodiol metabolite is quantified by LC-MS/MS using the d10-labeled epoxide as internal standard. For toxicity studies, cells are treated with carbamazepine-10,11-epoxide (1-100 uM) for 24-72 hours, and cell viability is assessed by MTT assay.
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| Animal Protocol |
For in vivo animal experiments, carbamazepine 10,11 epoxide-d10 is not typically administered to animals as a drug. For pharmacokinetic studies of carbamazepine, rats or mice are administered carbamazepine orally or intravenously (10-50 mg/kg). Blood samples are collected at multiple time points (0, 0.5, 1, 2, 4, 6, 8, 12, 24 hours). Carbamazepine 10,11 epoxide-d10 (fixed concentration) is added to plasma samples as internal standard before LC-MS/MS analysis to quantify carbamazepine-10,11-epoxide levels. For tissue distribution studies, organs (brain, liver, kidney) are harvested and homogenized. The internal standard is added before extraction to correct for matrix effects.
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| ADME/Pharmacokinetics |
Carbamazepine 10,11 epoxide-d10 has a molecular weight of 262.33 and is soluble in DMSO (125 mg/mL). The compound should be stored as a powder at -20degC for up to 3 years, and in solution at -80degC for up to 6 months or at -20degC for up to 1 month. The ten deuterium atoms (two per aromatic ring, positions 1-10) provide a mass shift of +10 Da, enabling clear differentiation from non-deuterated carbamazepine-10,11-epoxide (MW 252). The compound is stable and non-hygroscopic under normal storage conditions. Standard handling procedures for organic compounds should be followed.
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| Toxicity/Toxicokinetics |
Carbamazepine 10,11 epoxide-d10 is a stable isotope-labeled compound with minimal toxicity at analytical concentrations (ng-ug per sample). The non-deuterated parent compound, carbamazepine-10,11-epoxide, at high concentrations can cause neurotoxicity including dizziness, ataxia, and diplopia, as these are dose-dependent side effects of carbamazepine therapy related to epoxide accumulation. However, when used as an internal standard, the amount is negligible and poses no toxicity risk. Standard laboratory safety precautions for handling organic compounds and drug metabolites should be followed.
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| References | |
| Additional Infomation |
Carbamazepine 10,11 epoxide-d10 is an analytical standard and research tool, not an approved drug. No clinical trials have been conducted with the deuterated version for therapeutic purposes. The non-deuterated parent compound, carbamazepine-10,11-epoxide, is the active metabolite of carbamazepine, an FDA-approved anticonvulsant used for epilepsy, trigeminal neuralgia, and bipolar disorder. Carbamazepine 10,11 epoxide-d10 is used exclusively as an internal standard for quantitative LC-MS/MS analysis of carbamazepine and its epoxide metabolite in clinical and research settings for therapeutic drug monitoring (TDM). It is also used in pharmaceutical quality control for carbamazepine formulations and in studies of carbamazepine metabolism and drug-drug interactions. The compound is intended for research use only.
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| Molecular Formula |
C15H2D10N2O2
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|---|---|
| Molecular Weight |
262.33
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| Exact Mass |
252.089
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| CAS # |
1219804-16-6
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| Related CAS # |
Carbamazepine 10,11-epoxide;36507-30-9
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| PubChem CID |
76974847
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
390.2±52.0 °C at 760 mmHg
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| Flash Point |
189.8±30.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.687
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| LogP |
1.26
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
19
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| Complexity |
358
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1=C(C(=C2C(=C1[2H])C3(C(O3)(C4=C(C(=C(C(=C4N2C(=O)N)[2H])[2H])[2H])[2H])[2H])[2H])[2H])[2H]
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| InChi Key |
ZRWWEEVEIOGMMT-WJSNEECMSA-N
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| InChi Code |
InChI=1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)/i1D,2D,3D,4D,5D,6D,7D,8D,13D,14D
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| Chemical Name |
2,4,6,7,8,9,13,14,15,16-decadeuterio-3-oxa-11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
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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 | 3.8120 mL | 19.0600 mL | 38.1199 mL | |
| 5 mM | 0.7624 mL | 3.8120 mL | 7.6240 mL | |
| 10 mM | 0.3812 mL | 1.9060 mL | 3.8120 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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