Brivudine
Brivudine, also known as bromovinyl-deoxyuridine, 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.
1: GarcÃa Fernández V, Garrido Arévalo M, Labrada González E, Hidalgo Correas FJ. [Fatal drug-drug interaction between 5-fluorouracil and brivudine.]. Farm Hosp. 2013 Enero-Febrero;37(1):72-73. Spanish. PubMed PMID: 23461503.
2: Zhang NQ, Zhao L, Ma S, Gu M, Zheng XY. Potent anticancer effects of lentivirus encoding a Drosophila melanogaster deoxyribonucleoside kinase mutant combined with brivudine. Asian Pac J Cancer Prev. 2012;13(5):2121-7. PubMed PMID: 22901180.
3: Heinrich JC, Tuukkanen A, Schroeder M, Fahrig T, Fahrig R. 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. doi: 10.1007/s00432-011-1005-1. Epub 2011 Jul 22. PubMed PMID: 21833720.
4: Bleymehl K, Cinatl J, Schmidt-Chanasit J. Phenotypic and genetic characterization of varicella-zoster virus mutants resistant to acyclovir, brivudine and/or foscarnet. Med Microbiol Immunol. 2011 Aug;200(3):193-202. doi: 10.1007/s00430-011-0191-4. Epub 2011 Mar 4. Erratum in: Med Microbiol Immunol. 2012 Aug;201(3):403-5. PubMed PMID: 21373931.
5: Lahmer T, Hoffmann D, Heemann U, Küchle C, Frank H. Epstein-Barr virus encephalitis after kidney transplantation and successful treatment with brivudine. Transpl Int. 2010 Jun;23(6):e24-5. doi: 10.1111/j.1432-2277.2009.01045.x. Epub 2010 Jan 12. PubMed PMID: 20070626.
6: Rätz Bravo AE, Hofer S, Krähenbühl S, Ludwig C. Fatal drug-drug interaction of brivudine and capecitabine. Acta Oncol. 2009;48(4):631-3. doi: 10.1080/02841860802660502. PubMed PMID: 19165642.
7: Abraham S, Jones A, Toutous-Trellu L, Kerl-Bullani K, Chavaz P, Saurat JH, Piguet V. Linear Darier disease with herpes zoster superinfection treated successfully by brivudine. Br J Dermatol. 2006 Feb;154(2):365-7. PubMed PMID: 16433812.
8: Vij O, Bornfeld N, Roggendorf M, Fiedler M, Schilling H. [Brivudine as an alternative systemic therapy to aciclovir and ganciclovir in acute retinal necrosis syndrome due to varicella-zoster virus]. Klin Monbl Augenheilkd. 2003 Oct;220(10):710-5. German. PubMed PMID: 14577039.
9: Rabasseda X. Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs Today (Barc). 2003 May;39(5):359-71. Review. PubMed PMID: 12861349.
2: Zhang NQ, Zhao L, Ma S, Gu M, Zheng XY. Potent anticancer effects of lentivirus encoding a Drosophila melanogaster deoxyribonucleoside kinase mutant combined with brivudine. Asian Pac J Cancer Prev. 2012;13(5):2121-7. PubMed PMID: 22901180.
3: Heinrich JC, Tuukkanen A, Schroeder M, Fahrig T, Fahrig R. 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. doi: 10.1007/s00432-011-1005-1. Epub 2011 Jul 22. PubMed PMID: 21833720.
4: Bleymehl K, Cinatl J, Schmidt-Chanasit J. Phenotypic and genetic characterization of varicella-zoster virus mutants resistant to acyclovir, brivudine and/or foscarnet. Med Microbiol Immunol. 2011 Aug;200(3):193-202. doi: 10.1007/s00430-011-0191-4. Epub 2011 Mar 4. Erratum in: Med Microbiol Immunol. 2012 Aug;201(3):403-5. PubMed PMID: 21373931.
5: Lahmer T, Hoffmann D, Heemann U, Küchle C, Frank H. Epstein-Barr virus encephalitis after kidney transplantation and successful treatment with brivudine. Transpl Int. 2010 Jun;23(6):e24-5. doi: 10.1111/j.1432-2277.2009.01045.x. Epub 2010 Jan 12. PubMed PMID: 20070626.
6: Rätz Bravo AE, Hofer S, Krähenbühl S, Ludwig C. Fatal drug-drug interaction of brivudine and capecitabine. Acta Oncol. 2009;48(4):631-3. doi: 10.1080/02841860802660502. PubMed PMID: 19165642.
7: Abraham S, Jones A, Toutous-Trellu L, Kerl-Bullani K, Chavaz P, Saurat JH, Piguet V. Linear Darier disease with herpes zoster superinfection treated successfully by brivudine. Br J Dermatol. 2006 Feb;154(2):365-7. PubMed PMID: 16433812.
8: Vij O, Bornfeld N, Roggendorf M, Fiedler M, Schilling H. [Brivudine as an alternative systemic therapy to aciclovir and ganciclovir in acute retinal necrosis syndrome due to varicella-zoster virus]. Klin Monbl Augenheilkd. 2003 Oct;220(10):710-5. German. PubMed PMID: 14577039.
9: Rabasseda X. Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs Today (Barc). 2003 May;39(5):359-71. Review. PubMed PMID: 12861349.
| Chemical | |
|---|---|
| CAS Num | 69304-47-8 |
| Chemical Formula | C11H13BrN2O5 |
| Molecular Weight | 333.13 |
| IUPAC Chemical Name | 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
| Exact Mass | 332.00078 |
| Elemental Analysis | C, 39.66; H, 3.93; Br, 23.99; N, 8.41; O, 24.01 |
| Synonym | Bridic Brivox Brivudin Helpin Zerpex Zonavir and Zostex. Abbreviation |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C1NC(C(/C=C/Br)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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