Brivudine

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Brivudine
Systematic (IUPAC) name
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy- 5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Identifiers
CAS number	69304-47-8
ATC code	J05AB15
PubChem	446727
Chemical data
Formula	C11H13BrN2O5
Mol. mass	333.135 g/mol
Pharmacokinetic data
Bioavailability	30%
Metabolism	?
Half life	16 hours
Excretion	mainly renal
Therapeutic considerations
Pregnancy cat.	exclusion
Legal status
Routes	oral

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

Contents 1 History 2 Approvals 3 Mechanism of Action 4 The drug's name 5 Suppliers

[edit] 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.

[edit] Approvals

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

[edit] 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.

[edit] 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.

[edit] 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 and Spain.

v • d • e Antivirals, other than for HIV (primarily J05, also S01AD and D06BB) Anti-herpesvirus (DNA, I) purine analogue (guanine) (Aciclovir, Famciclovir, Ganciclovir, Penciclovir, Valaciclovir, Valganciclovir) • Vidarabine pyrimidine analogue (uridine) (Idoxuridine, Trifluridine) • Cidofovir Docosanol • Fomivirsen • Foscarnet • Tromantadine HPV/MC (DNA, I) Imiquimod • Podophyllotoxin Hepatitis B (DNA, VII) Adefovir • Clevudine • Interferon alfa-2b • Pegylated interferon alfa-2a • Entecavir • Lamivudine • Telbivudine • Tenofovir† Hepatitis C (RNA, IV) Pegylated interferon alpha • Ribavirin • Taribavirin† • Boceprevir† Picornavirus (RNA, IV) Pleconaril† Anti-influenza agents (RNA, V) Arbidol adamantane derivatives/M2 inhibitors (Amantadine, Rimantadine) neuraminidase inhibitors (Oseltamivir, Zanamivir, Peramivir†) HIV (Reverse, VI) See HIV pharm Other antiviral agents general (Inosine, Interferon) †Undergoing clinical trials, not FDA approved.