Brivudine
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MedKoo CAT#: 100103

CAS#: 69304-47-8

Description: 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.


Chemical Structure

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Brivudine
CAS# 69304-47-8

Theoretical Analysis

MedKoo Cat#: 100103
Name: Brivudine
CAS#: 69304-47-8
Chemical Formula: C11H13BrN2O5
Exact Mass: 332.00078
Molecular Weight: 333.13
Elemental Analysis: C, 39.66; H, 3.93; Br, 23.99; N, 8.41; O, 24.01

Price and Availability

Size Price Availability Quantity
200.0mg USD 150.0 Same day
500.0mg USD 250.0 Same day
1.0g USD 450.0 Same day
2.0g USD 750.0 Same day
5.0g USD 1450.0 Same day
10.0g USD 2250.0 Same day
20.0g USD 3750.0 Same day
100.0g USD 7950.0 2 Weeks
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Synonym: Bridic Brivox Brivudin Helpin Zerpex Zonavir and Zostex. Abbreviation: BVDU; Code name: RP101. Chemical structure name: (E)5(2bromovinyl)2deoxyuridine

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

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

SMILES Code: O=C1NC(C(/C=C/Br)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O

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).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Brivudine is a thymidine analogue with antiviral activity.
In vitro activity: 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. Reference: J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. https://link.springer.com/article/10.1007%2Fs00432-011-1005-1
In vivo activity: RP101 was tested as an anti-cancer drug in a rat model, and it was found that it improved chemotherapy. Reference: J Cancer Res Clin Oncol. 2011 Sep;137(9):1349-61. https://link.springer.com/article/10.1007%2Fs00432-011-1005-1

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 142.0 426.26
DMF 30.0 90.05
Ethanol 10.0 30.02
PBS (pH 7.2) 0.5 1.5

Preparing Stock Solutions

The following data is based on the product molecular weight 333.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. PMID: 21833720.
In vitro protocol: 1. 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. PMID: 21833720.
In vivo protocol: 1. 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. PMID: 21833720.

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1: García 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.

Brivudine

200.0mg / USD 150.0


Additional Information

According to http://en.wikipedia.org/wiki/Brivudine, Brivudine is approved for use in Germany and other European countries including Italy. Brivudine is a similar drug to acyclovir The compound was first synthesized by scientists at the University of Birmingham in the UK in the 1970s. It was shown to be a potent inhibitor of the herpes simplex virus Type 1 (HSV-1) as well as the varicella zoster virus (VZV) by Erik De Clercq at the Rega Institute for Medical Research in Belgium in 1979. In the 1980s the drug became commercially available in East Germany, where it was marketed as Helpin by a pharmaceutical company called Berlin-Chemie.