Brivudine (Bromovinyldeoxyuridine)
(Synonyms: 溴夫定; Bromovinyldeoxyuridine; BVDU) 目录号 : GC33923
An antiviral thymidine analog
Cas No.:69304-47-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Brivudine is a thymidine analog and inhibitor of herpes simplex virus 1 (HSV-1) and varicella-zoster virus (VZV) viral replication.1,2 Following conversion to a 5'-triphosphate form by viral kinases, brivudine is incorporated into viral DNA, inhibiting viral DNA polymerases and inducing strand breakage.2 Brivudine (0.02-0.04 μg/ml) inhibits VZV replication in primary human fibroblasts and inhibits cytopathogenic effects of the KOS HSV-1 strain in a panel of cell lines (MIC50s = 0.007-0.4 μg/ml).1,3 It selectively inhibits cytopathogenicity induced by HSV-1 strains over HSV-2, vaccinia virus, vesicular stomatitis virus, or deoxythymidine kinase-deficient HSV-1 strains in E6SM cells (MIC50s = 0.02, 2-10, 7, >400, and 40 μg/ml, respectively).1 Brivudine (5 and 15 mg/kg twice per day) increases survival in a mouse model of disseminated HSV-1 infection.
1.De Clercq, E., Desgranges, C., Herdewijn, P., et al.Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridineJ. Med. Chem.29(2)213-217(1986) 2.Kulikowski, T.Structure-activity relationships and conformational features of antiherpetic pyrimidine and purine nucleoside analogues. A reviewPharm. World Sci.16(2)127-138(1994) 3.De Clercq, E., Descamps, J., Verhelst, G., et al.Antiviral activity of 5-(2-halogenovinyl)-2'-deoxyuridinesCurr. Chemother. Infect. Dis.21372-1374(1980)
| Cas No. | 69304-47-8 | SDF | |
| 别名 | 溴夫定; Bromovinyldeoxyuridine; BVDU | ||
| Canonical SMILES | OC[C@@H]1[C@H](C[C@H](N2C(NC(C(/C=C/Br)=C2)=O)=O)O1)O | ||
| 分子式 | C11H13BrN2O5 | 分子量 | 333.14 |
| 溶解度 | DMSO : ≥ 330 mg/mL (990.57 mM) | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0017 mL | 15.0087 mL | 30.0174 mL |
| 5 mM | 0.6003 mL | 3.0017 mL | 6.0035 mL |
| 10 mM | 0.3002 mL | 1.5009 mL | 3.0017 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
RP101 (Brivudine) binds to heat shock protein HSP27 (HSPB1) and enhances survival in animals and pancreatic cancer patients
J Cancer Res Clin Oncol 2011 Sep;137(9):1349-61.PMID:21833720DOI:10.1007/s00432-011-1005-1.
Background: Several reports describe the importance of the chaperone HSP27 (HSPB1) in cancer progression, and the demand for drugs that modulate HSPB1-activity is increasing rapidly. We reported earlier that RP101 (Bromovinyldeoxyuridine, BVDU, Brivudine) improves the efficacy of chemotherapy in pancreatic cancer. Methods: Chemistry: Binding of RP101 and HSPB1 was discovered by affinity chromatography. Molecular and cell biology: HSPB1 in vitro transcription/translation (TNT), Pull down using RP101-coupled magnetic beads, Immuno Co-precipitations, Structural modeling of HSP27 (HSPB1), Introduction of point mutations into linear expression templates by PCR, Heat shock, Tumor Invasion. Animal experiments: Treatment of AH13r Sarcomas in SD-rats. Clinical Studies with late-stage pancreatic cancer patients: Pilot study, Dose finding study, Phase II study (NCT00550004). Results: Here, we report that RP101 binds in vitro to the heat shock protein HSPB1 and inhibits interaction with its binding partners. As a result, more activated CASP9 was detected in RP101-treated cancer cells. We modeled HSPB1-structure and identified the RP101 binding site. When we tested RP101 as an anti-cancer drug in a rat model, we found that it improved chemotherapy. In clinical studies with late-stage pancreatic cancer patients, the dose of 500 mg/day was safe and efficient, but 760 mg/day turned out to be too high for lightweight patients. Conclusions: The development of RP101 as a cancer drug represents a truly novel approach for prevention of chemoresistance and enhancement of chemosensitivity.
Experimental stroma herpes simplex keratitis. Influence of treatment with topical Bromovinyldeoxyuridine and trifluridine
Arch Ophthalmol 1982 Apr;100(4):653-6.PMID:6803747DOI:10.1001/archopht.1982.01030030655027.
Two compounds, Bromovinyldeoxyuridine ([E]-5-[2-bromovinyl]-2'-deoxyuridine) and trifluridine (5-trifluoromethyl-2' deoxyuridine) were compared for their efficacy in the topical treatment of experimental stroma herpetic keratitis produced by the injection of live herpes simplex virus, type 1, into the corneal stroma of rabbits. The trifluridine was used as 1% eyedrops, whereas Bromovinyldeoxyuridine was used as either 0.1% or 0.5% eyedrops. All three treatment regimens caused a substantial healing of stroma disease in comparison with placebo treatment. The Bromovinyldeoxyuridine (whether used as 0.1% or 0.5%) proved superior to 1% trifluridine eyedrops when the treatment was started one day after virus inoculation. However, Bromovinyldeoxyuridine and trifluridine were equally effective if the treatment was started seven days after infection. The 0.5% Bromovinyldeoxyuridine eyedrops seemed to be more effective in controlling the complicating severe iritis and secondary glaucoma than either 0.1% Bromovinyldeoxyuridine or 1% trifluridine. No toxic effects were observed with Bromovinyldeoxyuridine in any eye, whereas 1% trifluridine produced punctate epitheliopathy in some eyes.
Bromovinyldeoxyuridine and interferon treatment in ulcerative herpetic keratitis: a double masked study
Br J Ophthalmol 1989 Aug;73(8):604-7.PMID:2669938DOI:10.1136/bjo.73.8.604.
Bromovinyldeoxyuridine is a potent and safe antiherpes compound that in combination with a placebo treatment promoted the partial and complete healing of herpetic epithelial disease in 22 patients in average times of 4-6 days and 8.5 days respectively. However, when BVDU was combined with 1.5 X 10(6) IU of recombinant a 2C interferon, partial and complete healing times for keratitis in 19 patients were reduced to 2-6 days and 4-6 days respectively. No toxic effects of the medications were observed in any patient.
Bromovinyldeoxyuridine treatment of herpetic keratitis clinically resistant to other antiviral agents
Curr Eye Res 1991;10 Suppl:193-9.PMID:1650667DOI:10.3109/02713689109020379.
Patients suffering from dendritic and geographic corneal ulcers or herpetic stromal keratitis were treated with topical BVDU [(E)-5-(2-bromovinyl)-2'-deoxyuridine, Bromovinyldeoxyuridine] 0.1% eyedrops administered during the day only at 1-hour intervals. Treatment with other antiviral drugs, i.e., idoxuridine, trifluridine, vidarabine or Zovirax had failed to ameliorate the ocular disease in 102 patients when their treatment was switched to BVDU eyedrops. Under BVDU therapy, dendritic keratitis in 44 patients healed within an average 7.8 days. Similarly, geographic corneal ulcers in 26 patients and stromal keratitis in 32 patients healed within an average period of 11.2 days and 30.7 days, respectively. Associated therapy with topical corticosteroids was stopped in 65 patients when the antiviral treatment was switched. However, topical corticosteroids had to be used together with BVDU drops to arrest stromal inflammation in 49 patients. Ultimately, 36 patients became corticosteroid-dependent. Except for local hypersensitivity reaction in three patients, BVDU eyedrops did not cause any toxic side effects.
Efficacy of Bromovinyldeoxyuridine in the treatment of herpes simplex virus and varicella-zoster virus eye infections
Antiviral Res 1984 Oct;4(5):281-91.PMID:6335020DOI:10.1016/0166-3542(84)90033-0.
As has been established in rabbits, (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) is superior to 5-iodo-2'-deoxyuridine (IDU) in the topical treatment of epithelial HSV-1 (herpes simplex virus type 1) keratitis, and superior to 5-trifluoromethyl-2'-deoxyuridine (TFT) in the topical treatment of deep stromal HSV-1 keratitis and HSV-1 uveitis. BVDU 0.1% eye drops have also proven efficacious in the treatment of patients with dendritic corneal ulcers, geographic corneal ulcers and stromal keratitis, and combined treatment of BVDU 0.1% eye drops with oral BVDU at 375 mg/day for 5 days led to a prompt healing of keratouveitis and skin lesions in patients with ophthalmic herpes zoster.