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| Targets |
(Rac)-Emtricitabine S-oxide is a degradation product and metabolite of emtricitabine. The parent drug, emtricitabine, targets HIV-1 reverse transcriptase, a viral enzyme essential for HIV replication. As the S-oxide metabolite, this compound has significantly reduced antiviral activity compared to the parent drug. The compound serves as an impurity marker and degradation product for quality control in emtricitabine pharmaceutical formulations. It does not have direct therapeutic targets as it is an inactive metabolite.
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| ln Vitro |
In vitro studies have shown that (Rac)-Emtricitabine S-oxide exhibits significantly reduced activity against HIV-1 reverse transcriptase compared to emtricitabine. While emtricitabine has an EC50 of approximately 0.01-0.1 uM against HIV-1, the S-oxide metabolite has substantially lower potency. This compound is primarily used as a reference standard in analytical methods such as HPLC for detecting degradation products in emtricitabine drug substance and drug product. No significant in vitro cytotoxicity has been reported at concentrations used for analytical purposes.
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| ln Vivo |
No direct in vivo activity studies have been published for (Rac)-Emtricitabine S-oxide. As a degradation product of emtricitabine, its in vivo levels are typically low following oral administration of emtricitabine, as the parent drug undergoes limited oxidation to the S-oxide. The compound is not intended for therapeutic use and has no known in vivo efficacy. In pharmacokinetic studies of emtricitabine, the S-oxide metabolite is monitored as a minor metabolite.
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| Enzyme Assay |
No specific enzyme/receptor binding protocols have been established for (Rac)-Emtricitabine S-oxide as it is a degradation product rather than a direct ligand. For analytical purposes, standard HPLC methods are used to quantify this compound in emtricitabine drug substance. Typical conditions include a C18 reverse-phase column (e.g., 250 mm × 4.6 mm, 5 um), mobile phase of phosphate buffer (pH 3.0) with acetonitrile gradient, flow rate of 1.0 mL/min, and detection at 260 nm. For LC-MS/MS analysis, electrospray ionization in positive ion mode with m/z transitions specific to the S-oxide can be used.
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| Cell Assay |
For cellular studies evaluating the activity of (Rac)-Emtricitabine S-oxide, standard protocols involve culturing HIV-susceptible cell lines such as MT-4 cells in RPMI-1640 with 10% FBS. Cells are infected with HIV-1 and treated with varying concentrations of the test compound for 5-7 days. Antiviral activity is assessed by measuring HIV-1 p24 antigen levels in culture supernatants by ELISA. Cytotoxicity is evaluated using MTT assays. However, the S-oxide is known to have significantly lower antiviral activity than the parent drug and is primarily used as an analytical standard rather than for cellular activity studies.
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| Animal Protocol |
For in vivo animal studies, (Rac)-Emtricitabine S-oxide is not typically administered as a test compound. Instead, it is monitored as a metabolite in pharmacokinetic studies of emtricitabine. In such studies, animals (e.g., rats or dogs) are administered emtricitabine orally or intravenously at doses of 1-50 mg/kg. Blood samples are collected at predetermined time points, and plasma concentrations of emtricitabine and its S-oxide metabolite are measured by LC-MS/MS. The S-oxide is typically a minor metabolite, with Cmax values usually below 5-10% of the parent drug. For reference standard qualification, no specific animal studies are required.
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| ADME/Pharmacokinetics |
For (Rac)-Emtricitabine S-oxide as a degradation product, no direct pharmacokinetic studies have been published. For the parent drug emtricitabine, key PK parameters in humans include oral bioavailability of approximately 93%, plasma half-life of about 10 hours, low protein binding (<4%), and renal excretion of unchanged drug (approximately 70% of dose). The S-oxide metabolite is typically a minor component in plasma, with exposure levels much lower than the parent drug. The compound has a predicted logP that is lower than emtricitabine due to the polar S-oxide group.
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| Toxicity/Toxicokinetics |
Safety data for (Rac)-Emtricitabine S-oxide indicates the compound is for research use only as an analytical reference standard. Standard laboratory safety precautions should be followed: wear protective gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood. Avoid inhalation, ingestion, and contact with skin and eyes. The compound should be stored at -20degC, protected from light and moisture. While specific toxicity data for the S-oxide is limited, the parent compound emtricitabine is generally well-tolerated in clinical use, but this product is not for human therapeutic use.
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| Additional Infomation |
(Rac)-Emtricitabine S-oxide is a degradation product and metabolite of the antiviral drug emtricitabine, which is a potent nucleoside reverse transcriptase inhibitor used for the treatment of HIV-1 infection. This compound is also known as Emtricitabine Degradant-III and is used as a reference standard in pharmaceutical quality control for detecting degradation products in emtricitabine drug substance and drug product. As an analytical standard, it is essential for method validation and stability studies. No clinical trial information is available for this degradation product, and it is not approved for human therapeutic use.
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| Molecular Formula |
C8H10FN3O4S
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| Molecular Weight |
263.25
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| CAS # |
2733287-29-9
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| Related CAS # |
Emtricitabine S-oxide; 152128-77-3
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| Appearance |
Solid powder
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| Synonyms |
(Rac)-Emtricitabine sulfoxide; (Rac)-Emtricitabine Degradant-III
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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 | 3.7987 mL | 18.9934 mL | 37.9867 mL | |
| 5 mM | 0.7597 mL | 3.7987 mL | 7.5973 mL | |
| 10 mM | 0.3799 mL | 1.8993 mL | 3.7987 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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