Brivudine

Drugbox
IUPAC_name = 5- [("E")-2-bromoethenyl] -1- [(2"R",4"S",5"R")-4-hydroxy-
5-(hydroxymethyl)oxolan-2-yl] pyrimidine-2,4-dione

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CAS_number=69304-47-8
ATC_prefix=J05
ATC_suffix=AB15
PubChem=446727
DrugBank=
C = 11 | H = 13 | Br = 1 | N = 2 | O = 5
molecular_weight = 333.135 g/mol
bioavailability= 30%
metabolism =
elimination_half-life= 16 hours
excretion = mainly renal
pregnancy_category = exclusion
legal_status =
routes_of_administration= oral

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.

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 Brivudin, Helpin, Zerpex, Zonavir and Zostex.

uppliers

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 and Spain.