Brivudine

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Brivudine
Brivudine - Brivudin.svg
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 International Drug Names
Pregnancy cat. exclusion
Legal status ?
Routes oral
Pharmacokinetic data
Bioavailability 30%
Half-life 16 hours
Excretion mainly renal
Identifiers
CAS number 69304-47-8 N
ATC code J05AB15
PubChem CID 446727
ChemSpider 394011 YesY
UNII 2M3055079H YesY
ChEMBL CHEMBL31634 YesY
Chemical data
Formula C11H13BrN2O5 
Mol. mass 333.135 g/mol
 N (what is this?)  (verify)

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

History[edit]

Brivudine is a similar drug to acyclovir[clarification needed]. 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[edit]

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

Mechanism of Action[edit]

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[edit]

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[edit]

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[edit]

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[edit]

  1. ^ Wilhelmus KR (2010). "Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis". Cochrane Database Syst Rev 12: CD002898. doi:10.1002/14651858.CD002898.pub4. PMID 21154352.