Structure via PubChem · Public domain (PubChem)
brivudine
Sign in to saveAlso known as 5-(2-bromovinyl)-2'-deoxyuridine
Brivudine (trade names Zostex, Mevir, Brivir, among others) is an antiviral drug used in the treatment of herpes zoster ("shingles"). Like other antivirals, it acts by inhibiting replication of the target virus.
Chemical data
- Formula
- C11H13BrN2O5
- Molecular weight
- 333.13 g/mol
- IUPAC name
- 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)CO)O
- InChIKey
- ODZBBRURCPAEIQ-PIXDULNESA-N
- XLogP
- -0.4
- Polar surface area
- 99.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- viral disease, pancreatic carcinoma, colorectal cancer
via ChEMBL · EBI
Research
468 papers- Efficacy and safety of brivudine for the treatment of herpes zoster: a systematic review and meta-analysis.The Journal of dermatological treatment · 2024
- Herpes zoster: A Review of Clinical Manifestations and Management.Viruses · 2022
- Treatment with Brivudine in Immunocompromised Pediatric Patients with Herpes Zoster.Chemotherapy · 2023
- Recommendations for the management of herpes zoster.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2007
- Brivudine as a successful treatment for herpes zoster combined with chickenpox.Postepy dermatologii i alergologii · 2025
via PubMed
Wikidata facts
- Mass
- 332.001
Show 4 more facts
- chemical formula
- C₁₁H₁₃BrN₂O₅
- canonical SMILES
- C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)CO)O
- isomeric SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)CO)O
- Commons category
- Brivudine
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Interactions
- Pharmacology
- Spectrum of activity
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Manufacturing
- History
- Etymology
- Research
- See also
- References
Brivudine (trade names Zostex, Mevir, Brivir, among others) is an antiviral drug used in the treatment of herpes zoster ("shingles"). Like other antivirals, it acts by inhibiting replication of the target virus.
==Medical uses== Brivudine is used for the treatment of herpes zoster in adult patients. It is taken orally once daily, in contrast to aciclovir, valaciclovir and other antivirals. A study has found that it is more effective than aciclovir, but this has been disputed because of a possible conflict of interest on part of the study authors. While brivudine is approved in several European countries for the treatment of herpes zoster, it has not received approval in the USA or Canada. In these non-approving countries Sorivudine is preferred over Brivudine.
Excerpted from Wikipedia’s “brivudine” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0