| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| 2g | |||
| 5g | |||
| Other Sizes |
| Targets |
Brivudine targets viral DNA polymerase by acting as a thymidine analog that is incorporated into viral DNA. It is selectively phosphorylated by viral thymidine kinase (TK) to its active triphosphate form, which then competes with deoxythymidine triphosphate for incorporation into the growing viral DNA strand. Once incorporated, brivudine triphosphate acts as a chain terminator, blocking the action of DNA polymerases and thus inhibiting viral replication. It has high, selective activity against VZV and herpes simplex virus type 1 (HSV-1).
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| ln Vitro |
A thymidine analogue called brudine is integrated into the DNA of viruses. It prevents DNA polymerase from working, which stops viruses from replicating. Compared to reference chemicals like acyclovir or penciclovir, it exhibits a better antiviral impact against the varicella-zoster virus [1]. It exhibits highly selective activity against the varicella zoster virus (VZV) and prevents its replication, either by acting as a substitute substrate for deoxythymidine triphosphate, which breaks the viral DNA chain, or by competitively inhibiting the viral DNA polymerase [2].
In vitro, brivudine blocks the action of DNA polymerases, thereby inhibiting viral replication. It exhibits highly selective activity against VZV and prevents its replication. Brivudine has been shown to downregulate the multifunctional DNA repair enzyme APEX nuclease 1, resulting in the inhibition of DNA repair and the induction of apoptosis. It may also inhibit the expression of STAT3, leading to the downregulation of vascular endothelial growth factor (VEGF). BVDU has been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy. |
| ln Vivo |
Brivudine was found to be more effective than acyclovir at 125 mg once daily in lowering the length of postherpetic neuralgia and the time it took for new blisters to form [1].
In vivo, brivudine is effective in the treatment of herpes zoster. At a dose of 125 mg once daily, brivudine was found to be more effective than acyclovir in lowering the length of postherpetic neuralgia and the time it took for new blisters to form. The efficacy of brivudine has been documented in a number of clinical trials in patients with herpesvirus-related infections. Its antiviral activity against VZV in vivo is mediated through selective inhibition of viral DNA polymerase, resulting in reduced viral load and accelerated lesion healing. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for brivudine typically involve measuring its inhibition of viral DNA polymerase. The enzyme is incubated with a DNA template, nucleotide substrates, and varying concentrations of brivudine triphosphate, and the extent of DNA synthesis is measured using radioactive or fluorescent methods. The IC50 for inhibition of DNA polymerase activity is determined from dose-response curves. Selectivity is assessed by comparing activity against viral versus host DNA polymerases.
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| Cell Assay |
In vitro cellular assays for brivudine are performed using virus-infected cell lines, such as VZV- or HSV-1-infected cells. Cells are treated with varying concentrations of brivudine, and viral replication is assessed by measuring the production of viral antigens or by plaque reduction assays. Cytotoxicity is evaluated using MTT assays to determine the selectivity index. The compound's ability to induce apoptosis is assessed by measuring caspase activity or DNA fragmentation. Chemosensitizing effects are evaluated in combination with chemotherapeutic agents.
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| Animal Protocol |
In vivo animal experiments for brivudine are conducted in animal models of herpesvirus infection, such as guinea pigs or mice infected with VZV or HSV-1. Animals are treated with brivudine via oral administration, and viral load, lesion development, and survival are monitored. Pharmacodynamic endpoints include measurement of viral DNA in tissues and assessment of clinical signs. However, detailed protocols are not extensively documented in the available literature.
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| ADME/Pharmacokinetics |
Brivudine has a molecular weight of 333.14 g/mol and a molecular formula of C11H13BrN2O5. It is a white to yellow crystalline powder, soluble in DMSO and methanol. The compound should be stored at -20°C under an inert atmosphere. Brivudine has a logP of -0.4, indicating moderate hydrophilicity. After oral administration, it is well absorbed and reaches therapeutic concentrations in plasma. It is metabolized and excreted primarily via the kidneys.
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| Toxicity/Toxicokinetics |
Brivudine is generally well-tolerated. Common adverse effects include nausea, headache, and dizziness. Serious adverse effects are rare but may include hepatotoxicity and bone marrow suppression. The compound is contraindicated in patients with severe hepatic impairment and those taking certain medications that interact with its metabolism. Brivudine should be used with caution in patients with renal impairment. It is not approved in the United States and Canada but is approved in some European countries.
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| References | |
| Additional Infomation |
Brivudine is used to treat herpes zoster. While not yet approved in the United States and Canada, it is approved in some European countries. Brivudine is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing effects. In vitro studies have shown that bromovinyldeoxyuridine (BVDU) downregulates the expression of the multifunctional DNA repair enzyme APEX nuclease 1, thereby inhibiting DNA repair and inducing apoptosis. Furthermore, the drug may inhibit the expression of STAT3 (signal transduction and transcription activator 3), leading to the downregulation of vascular endothelial growth factor (VEGF). Studies have also found that BVDU can inhibit the upregulation of drug resistance genes (Mdr1 and DHFR) during chemotherapy. In summary, BVDU treatment-related gene expression changes may reduce or prevent chemosensitivity. In addition, in vitro experiments have shown that the drug can enhance the cytolytic activity of NK-92 natural killer cells against pancreatic cancer cell lines.
Brivudine is an oral thymidine analog indicated for the early treatment of acute herpes zoster in immunocompetent adults. It is also known as bromovinyl-deoxyuridine (BVDU), Brivox, Helpin, Zerpex, and RP101. Brivudine is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. It has been studied for its potential to enhance the cytolytic activity of NK-92 natural killer cells towards pancreatic cancer cell lines. Brivudine is a research compound with therapeutic applications in herpesvirus infections. |
| Molecular Formula |
C11H13BRN2O5
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|---|---|
| Molecular Weight |
333.13
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| Exact Mass |
332
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| Elemental Analysis |
C, 39.66; H, 3.93
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| CAS # |
69304-47-8
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| Related CAS # |
69304-47-8;80860-82-8 (phosphate);
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| PubChem CID |
446727
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| Appearance |
White to off-white solid powder
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| Density |
1.9±0.1 g/cm3
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| Boiling Point |
382.9ºC at 760 mmHg
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| Melting Point |
165ºC
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| Flash Point |
185.4ºC
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| Index of Refraction |
1.709
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| LogP |
-0.8
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
19
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| Complexity |
450
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| Defined Atom Stereocenter Count |
3
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| SMILES |
Br/C(/[H])=C(\[H])/C1C(N([H])C(N(C=1[H])[C@@]1([H])C([H])([H])[C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])=O)=O
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| InChi Key |
ODZBBRURCPAEIQ-PIXDULNESA-N
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| InChi Code |
InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
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| Chemical Name |
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
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| Synonyms |
Bromovinyldeoxyuridine;BVDU
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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) |
DMSO: 67 mg/mL(201.12 mM) Water: 6 mg/mL(18.01 mM) Ethanol: 17 mg/mL(51.03 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 10 mg/mL (30.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 100.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 10 mg/mL (30.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 100.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 10 mg/mL (30.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0018 mL | 15.0092 mL | 30.0183 mL | |
| 5 mM | 0.6004 mL | 3.0018 mL | 6.0037 mL | |
| 10 mM | 0.3002 mL | 1.5009 mL | 3.0018 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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