Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H13BrN2O5 |
| Molecular Weight | 333.135 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(\C=C\Br)C(=O)NC2=O
InChI
InChIKey=ODZBBRURCPAEIQ-PIXDULNESA-N
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/international/brivudine.html | https://www.ncbi.nlm.nih.gov/pubmed/19281225 | https://www.ncbi.nlm.nih.gov/pubmed/17948980 | https://www.ncbi.nlm.nih.gov/pubmed/21833720
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/brivudine.html | https://www.ncbi.nlm.nih.gov/pubmed/19281225 | https://www.ncbi.nlm.nih.gov/pubmed/17948980 | https://www.ncbi.nlm.nih.gov/pubmed/21833720
Brivudine (trade names Zostex, Mevir, Brivir, among others) is an antiviral drug used in the treatment of herpes zoster ("shingles"). Brivudine is an analog of the nucleoside thymidine. The active compound is brivudine 5'-triphosphate, which is formed in subsequent phosphorylations by viral (but not human) thymidine kinase and presumably by the nucleoside-diphosphate kinase. Brivudine 5'-triphosphate works because it is incorporated into the viral DNA, but then blocks the action of DNA polymerases, thus inhibiting viral replication. 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. The drug is contraindicated in patients undergoing immunosuppression (for example because of an organ transplant) or cancer therapy, especially with fluorouracil (5-FU) and chemically related (pro)drugs such as capecitabine and tegafur, as well as the antimycotic drug flucytosine, which is also related to 5-FU. It has not been proven to be safe for children and pregnant or breastfeeding women. The drug is generally well tolerated. The only common side effect is nausea (in 2% of patients). Less common side effects (<1%) include a headache, increased or lowered blood cell counts (granulocytopenia, anemia, lymphocytosis, monocytosis), increased liver enzymes, and allergic reactions. Brivudine is approved for use in a number of European countries including Austria, Belgium, Germany, Greece, Italy, Portugal, Spain, and Switzerland.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3035076/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVUDINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10348194/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
BRIVUDINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5% |
BRIVUDINE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
125 mg 1 times / day multiple, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: multiple Dose: 125 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
125 mg 4 times / day multiple, oral Recommended Dose: 125 mg, 4 times / day Route: oral Route: multiple Dose: 125 mg, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis of some new benzisothiazolone and benzenesulfonamide derivatives of biological interest starting from saccharin sodium. | 2013-10 |
|
| Characterization of pyrimidine nucleoside phosphorylase of Mycoplasma hyorhinis: implications for the clinical efficacy of nucleoside analogues. | 2012-07-01 |
|
| Efficacy of select antivirals against Cryptosporidium parvum in vitro. | 1998-11-01 |
|
| Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus. | 1997-08 |
|
| Antiviral efficacies of famciclovir, valaciclovir, and brivudin in disseminated herpes simplex virus type 1 infection in mice. | 1997 |
|
| Understanding the binding of 5-substituted 2'-deoxyuridine substrates to thymidine kinase of herpes simplex virus type-1. | 1996-11-22 |
|
| Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. | 1995-12 |
|
| Susceptibilities of several drug-resistant herpes simplex virus type 1 strains to alternative antiviral compounds. | 1995-07 |
|
| Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. | 1995-04 |
|
| Lack of stereospecificity of some cellular and viral enzymes involved in the synthesis of deoxyribonucleotides and DNA: molecular basis for the antiviral activity of unnatural L-beta-nucleosides. | 1995 |
|
| Synthesis and antiherpes virus activity of 1,5-anhydrohexitol nucleosides. | 1993-07-09 |
|
| Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro. | 1990-07 |
|
| Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine. | 1989-08 |
|
| Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides. | 1989-02 |
|
| Phosphonoformate and phosphonoacetate derivatives of 5-substituted 2'-deoxyuridines: synthesis and antiviral activity. | 1988-09 |
|
| Comparison of two bromovinyl nucleoside analogs, 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil and E-5-(2-bromovinyl)-2'-deoxyuridine, with acyclovir in inhibition of Epstein-Barr virus replication. | 1988-07 |
|
| Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2'-deoxycytidine-related compounds. | 1988-01 |
|
| Novel acyclic adenosine analogs inhibit Epstein-Barr virus replication. | 1987-09 |
|
| 2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. | 1987-07 |
|
| In vitro and in vivo antiviral activity of 2'-fluorinated arabinosides of 5-(2-haloalkyl)uracil. | 1987-06 |
|
| Selective inhibitory effect of (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine and 2'-nor-cyclic GMP on adenovirus replication in vitro. | 1987-02 |
|
| Inhibiting effect of (RS)-9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine on varicella-zoster virus replication in cell culture. | 1987-01 |
|
| Effect of antiviral agents on replication of herpes simplex virus type 1 in brain cultures. | 1986-12 |
|
| A novel selective broad-spectrum anti-DNA virus agent. | 1986-10-02 |
|
| Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs. | 1986-03 |
|
| Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine. | 1986-02 |
|
| Activities of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and its metabolites against herpes simplex virus types 1 and 2 in cell culture and in mice infected intracerebrally with herpes simplex virus type 2. | 1986-01 |
|
| Selective in vitro and in vivo activities of 5-(2-haloalkyl)pyrimidine nucleoside analogs, particularly 5-(2-chloroethyl)-2'-deoxyuridine, against herpes simplex virus. | 1985-08 |
|
| Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents. | 1985-06 |
|
| Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus. | 1985-06 |
|
| Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines. | 1985-05 |
|
| 5-substituted deoxyuridines--structural requirements for antiviral activity against herpes simplex virus types 1 and 2 and possible biochemical basis for relative potency. | 1984-06 |
|
| In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds. | 1984-06 |
|
| Synthesis of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine and related analogues: potent and unusually selective antiviral activity of (E)-5-(3,3,3-trifluoro-1-propenyl)-2'-deoxyuridine against herpes simplex virus type 1. | 1984-03 |
|
| Oral antiviral drugs in experimental herpes simplex keratitis. | 1983-12 |
|
| Efficacy and selectivity of some nucleoside analogs as anti-human cytomegalovirus agents. | 1983-10 |
|
| Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity. | 1983-09 |
|
| Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines. | 1983-09 |
|
| Synergistic antiviral activity of acyclovir and interferon on human cytomegalovirus. | 1983-09 |
|
| Efficacy of (E)-5-(2-bromovinyl)-2'-deoxyuridine against different herpes simplex virus strains in cell culture and against experimental herpes encephalitis in mice. | 1982-10 |
|
| Efficiency and selectivity of (E)-5-(2-bromovinyl)-2'-deoxyuridine and some other 5-substituted 2'-deoxypyrimidine nucleosides as anti-herpes agents. | 1982-05 |
|
| Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus. | 1982-02 |
|
| In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds. | 1982-01 |
|
| Antiherpes activity of [E]-5-(1-propenyl)-2'-deoxyuridine and 5-(1-propenyl)-1-beta-D-arabinofuranosyluracil. | 1981-11 |
|
| Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases. | 1981-09 |
|
| Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils. | 1981-07 |
|
| Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine. | 1981-05 |
|
| Anti-herpes simplex virus and anti-human cell growth activity of E-5-propenyl-2'-deoxyuridine and the concept of selective protection in antivirus chemotherapy. | 1980-12 |
|
| (E)-5-(2-bromovinyl)-2'-Deoxyuridine in the treatment of experimental herpes simplex keratitis. | 1980-01 |
|
| (E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent. | 1979-06 |
Sample Use Guides
Brivudin was given as one 125-mg tablet every 6 hours.
Route of Administration:
Oral
HT1080 cells were treated with Gemcitabine (10 ng/ml) with and without RP101 (Brivudine) (30 mkM). After trypsinisation, the number of living cells was determined using the Cell Counter and Analyzer System CASY TT (Schärfe System GmbH, Reutlingen, Germany). The treatment of HT-1080 cells with Gemcitabine together with RP101 reduced penetration through matrigel by 30–50% compared to cells treated with Gemcitabine alone
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WHO-ATC |
J05AB15
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FDA ORPHAN DRUG |
247807
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NCI_THESAURUS |
C471
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EU-Orphan Drug |
EU/3/09/703
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NCI_THESAURUS |
C281
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C1557
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QJ05AB15
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CHEMBL31634
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100000088646
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59161
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C020235
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Brivudine
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DTXSID0045755
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2M3055079H
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ACTIVE MOIETY
