| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 100mg |
| Targets |
HIV-1 reverse transcriptase (RT) and Hepatitis B virus (HBV) polymerase. As a nucleoside analog, it acts as a chain terminator during viral DNA synthesis.
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|---|---|
| ln Vitro |
Emtricitabine triphosphate, the active form, is a robustly efficacious inhibitor of HIV-1 reverse transcriptase and HBV polymerase. It competes with the natural substrate deoxycytidine 5'-triphosphate (dCTP) for incorporation into the growing viral DNA strand. Once incorporated, it acts as a chain terminator because it lacks the necessary 3'-hydroxyl group for further nucleotide addition, thus halting viral DNA replication.
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| ln Vivo |
The in vivo activity is attributed to the parent drug, Emtricitabine. Once administered, Emtricitabine is taken up by cells and converted to its triphosphate form. This active anabolite has a long intracellular half-life (approximately 39 hours), which allows for once-daily dosing in the clinic. It has demonstrated robust efficacy in reducing HIV-1 viral load and is a standard component of HAART (Highly Active Antiretroviral Therapy).
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| Enzyme Assay |
A standard non-cellular assay to determine NRTI activity is a polymerase inhibition assay using purified recombinant HIV-1 reverse transcriptase (RT). In this assay, a synthetic RNA or DNA template is incubated with a complementary primer, dNTPs (including radiolabeled dCTP), HIV-1 RT, and varying concentrations of Emtricitabine triphosphate. The reaction is stopped, and the amount of DNA synthesized is measured by capturing the labeled product. The IC₅0 is calculated as the concentration needed to inhibit the polymerase activity by 50%.
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| Cell Assay |
As this is the active anabolite, it is generally not applied directly to cells in culture because it is highly charged and cell-impermeable. The cellular assay is performed with the parent drug, Emtricitabine. Cells (e.g., human T-cell line MT-2) are infected with HIV-1 and treated with various concentrations of Emtricitabine. After several days of culture, the antiviral effect is measured by quantifying a marker of viral replication, such as p24 antigen production in the supernatant using an ELISA kit, or by observing the cytopathic effect (cell death).
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| Animal Protocol |
In vivo studies are performed with the parent drug, Emtricitabine, not its triphosphate salt. A common animal model is a murine model of retroviral infection using the Friend retrovirus or a humanized mouse model (Hu-PBMC-NOD/SCID mouse) infected with HIV-1. Emtricitabine is administered orally to the mice at various daily doses. The primary outcome measure is the plasma viral load, determined by RT-qPCR, at various time points post-infection to calculate the dose-dependent reduction in viral replication.
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| ADME/Pharmacokinetics |
The PK properties apply to the parent drug, Emtricitabine. It is well-absorbed orally with a bioavailability >90%. It is minimally bound to human plasma proteins (<4%). The terminal plasma half-life is about 10 hours, but the intracellular half-life of the active triphosphate is 39 hours. It is primarily excreted unchanged in urine by a combination of glomerular filtration and active tubular secretion.
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| Toxicity/Toxicokinetics |
No specific toxicity data for the triphosphate salt is provided. The safety profile of the parent drug, Emtricitabine, is well-established from clinical use. Common side effects are generally mild and include headache, nausea, and diarrhea. It can cause lactic acidosis and severe hepatomegaly with steatosis in some cases, though this is rare. It is generally well-tolerated.
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| References |
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| Additional Infomation |
Emtricitabine is a cornerstone of modern HIV therapy. Its triphosphate form is the key active metabolite. The tetrasodium salt is a high-purity chemical form used for biochemical studies to validate the mechanism of action. The triphosphate is not administered as a drug itself due to its poor oral bioavailability and cellular penetration. This anabolite is a substrate for HIV-1 RT.
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| Molecular Formula |
C8H9FN3NA4O12P3S
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|---|---|
| Molecular Weight |
575.113730192184
|
| Exact Mass |
574.869
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| CAS # |
1188407-46-6
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| Related CAS # |
Emtricitabine triphosphate;145819-92-7;143491-57-0;Emtricitabine (BW1592);145819-92-7;Emtricitabine triphosphate ((-)-Emtricitabine triphosphate)
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| PubChem CID |
132585232
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
32
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| Complexity |
818
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| Defined Atom Stereocenter Count |
2
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| SMILES |
S1C[C@@H](N2C(N=C(C(=C2)F)N)=O)O[C@H]1COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+]
|
| InChi Key |
UVCVKFWKKXBGTF-YPNYOHIOSA-J
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| InChi Code |
InChI=1S/C8H13FN3O12P3S.4Na/c9-4-1-12(8(13)11-7(4)10)5-3-28-6(22-5)2-21-26(17,18)24-27(19,20)23-25(14,15)16;;;;/h1,5-6H,2-3H2,(H,17,18)(H,19,20)(H2,10,11,13)(H2,14,15,16);;;;/q;4*+1/p-4/t5-,6+;;;;/m0..../s1
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| Chemical Name |
tetrasodium;[[[(2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy-oxidophosphoryl]oxy-oxidophosphoryl] phosphate
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
H2O : 125 mg/mL (217.35 mM)
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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 | 1.7388 mL | 8.6940 mL | 17.3880 mL | |
| 5 mM | 0.3478 mL | 1.7388 mL | 3.4776 mL | |
| 10 mM | 0.1739 mL | 0.8694 mL | 1.7388 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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