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Brivudine

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	exclusion
Routes of administration	oral
ATC code	J05AB15 (WHO)
Pharmacokinetic data
Bioavailability	30%
Elimination half-life	16 hours
Excretion	mainly renal
Identifiers
IUPAC name 5--1--1,2,3,4-tetrahydropyrimidine-2,4-dione
PubChem CID	446727
ChemSpider	394011
UNII	2M3055079H
ChEMBL	ChEMBL31634
CompTox Dashboard (EPA)	DTXSID0045755
Chemical and physical data
Formula	C11H13BrN2O5
Molar mass	333.135 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES Br=CC=1C(=O)NC(=O)N(C=1)2O((O)C2)CO
InChI 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 Key:ODZBBRURCPAEIQ-PIXDULNESA-N
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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 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 Meranini Centro America and Wyeth.

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