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Brivudine

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Brivudine

Brivudine
Systematic (IUPAC) name
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Clinical data
AHFS/Drugs.com
Pregnancy cat.
  • exclusion
Legal status
?
Routes oral
Pharmacokinetic data
Bioavailability 30%
Half-life 16 hours
Excretion mainly renal
Identifiers
CAS number  N
ATC code J05
PubChem
ChemSpider  YesY
UNII  YesY
ChEMBL  YesY
Chemical data
Formula C11H13BrN2O5 
Mol. mass 333.135 g/mol
 N   

Brivudine is an antiviral drug used in the treatment of herpes zoster.

History

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.

Approvals

Brivudine is approved for use in Germany and other European countries including Italy.

Mechanism of Action

Brivudine is an analogue of the nucleoside thymidine. The drug works because it is able to be incorporated into the viral DNA, but then blocks the action of DNA polymerases, thus inhibiting viral replication. The active compound is the 5'-triphosphate of BVDU, which is formed in subsequent phosphorylations by viral thymidine kinase and presumably by nucleoside diphosphate kinase.

Research

A Cochrane Systematic Review examined the effectiveness of multiple antiviral drugs in the treatment of herpes simplex virus epithelial keratitis. Brivudine was found to be significantly more effective than idoxuridine in increasing the number of successfully healed eyes of participants.[1]

The drug's name

Brivudine derives from the drug's chemical name of bromovinyldeoxyuridine or BVDU for short. The drug's full chemical description is (E)-5-(2-bromovinyl)-2-deoxyuridine. It is also sold as Bridic, Brivox, Brivudin, Helpin, Zerpex, Zonavir and Zostex.

Suppliers

Brivudine main supplier is Berlin-Chemie, now part of Italy's Menarini Group. The drug is approved for sale in Austria, Belgium, Germany, Greece, Italy, Luxembourg, Portugal and Spain. In Central America is provided Menarini Centro America and Wyeth.

References

  1. ^ Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev 12: CD002898.  
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