| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
|
||
| 500mg |
|
||
| 1g |
|
||
| 2g |
|
||
| 5g |
|
||
| Other Sizes |
|
Brivudine (Brivox; Helpin ;Zerpex; BVDU; RP101; bromovinyl-deoxyuridine) is a novel and potent uridine analogue and nucleoside analogue with pro-apoptotic and chemosensitizing activities. Brivudine is an analog of thymidine that is incorporated into the viral DNA. It blocks the action of DNA polymerases, thus inhibiting viral replication. It has a stronger antiviral effect against the varicella-zoster virus compared with reference compounds such as aciclovir or penciclovir. The efficacy of brivudine has been documented in a number of clinical trials in patients with herpesvirus-related infections, particularly in patients with herpes-zoster. Brivudin is an oral thymidine analogue indicated for the early treatment of acute herpes zoster in immunocompetent adults. It has high, selective activity against varicella zoster virus (VZV), inhibiting VZV replication, possibly through competitive inhibition of viral DNA polymerase, or by acting as an alternative substrate to deoxythymidine triphosphate, causing viral DNA strand breakage.
| 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].
|
|---|---|
| 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].
|
| References | |
| Additional Infomation |
Brivudine is used in the treatment of herpes zoster. Although not approved in the U.S. or Canada, it is approved in several European countries.
Brivudine is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. In vitro, bromovinyl-deoxyuridine (BVDU) 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. In addition, this agent may inhibit the expression of STAT3 (signal transducer and activator of transcription 3), which may result in the downregulation of vascular endothelial growth factor (VEGF). BVDU has also been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy. Overall, the gene expression changes associated with BVDU treatment result in the decrease or prevention of chemoresistance. In addition, this agent has been shown to enhance the cytolytic activity of NK-92 natural killer cells towards a pancreatic cancer cell line in vitro. |
| Molecular Formula |
C11H13BRN2O5
|
|---|---|
| Molecular Weight |
333.13
|
| Exact Mass |
332
|
| Elemental Analysis |
C, 39.66; H, 3.93
|
| CAS # |
69304-47-8
|
| Related CAS # |
69304-47-8;80860-82-8 (phosphate);
|
| PubChem CID |
446727
|
| Appearance |
White to off-white solid powder
|
| Density |
1.9±0.1 g/cm3
|
| Boiling Point |
382.9ºC at 760 mmHg
|
| Melting Point |
165ºC
|
| Flash Point |
185.4ºC
|
| Index of Refraction |
1.709
|
| LogP |
-0.8
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
19
|
| Complexity |
450
|
| Defined Atom Stereocenter Count |
3
|
| 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
|
| InChi Key |
ODZBBRURCPAEIQ-PIXDULNESA-N
|
| 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
|
| Chemical Name |
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
|
| Synonyms |
Bromovinyldeoxyuridine;BVDU
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO: 67 mg/mL(201.12 mM) Water: 6 mg/mL(18.01 mM) Ethanol: 17 mg/mL(51.03 mM) |
|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
