A halogenated thymidine, similar to acyclovir but with lower toxicity and increased activity against herpesviruses. Called also bromovinyl deosyuridine.
Brivudine
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| 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 | |
| Identifiers | |
| CAS number | 69304-47-8 |
| ATC code | J05AB15 |
| PubChem | 446727 |
| ChemSpider | 394011 |
| Chemical data | |
| Formula | C11H13BrN2O5 |
| Mol. mass | 333.135 g/mol |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 30% |
| Metabolism | ? |
| Half life | 16 hours |
| Excretion | mainly renal |
| Therapeutic considerations | |
| Pregnancy cat. |
exclusion |
| Legal status | |
| Routes | oral
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Brivudine is an antiviral drug used in the treatment of herpes zoster.
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History
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
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, 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.
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 | Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved. Read more |
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