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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/7561799Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7561799
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1795127 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438061 |
240.0 nM [Ki] | ||
Target ID: CHEMBL370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17948980 |
29.0 µM [EC50] | ||
Target ID: CHEMBL377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4009596 |
80.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Brivox Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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 Dec |
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Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine. | 1981 May |
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Antiherpes activity of [E]-5-(1-propenyl)-2'-deoxyuridine and 5-(1-propenyl)-1-beta-D-arabinofuranosyluracil. | 1981 Nov |
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Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus. | 1982 Feb |
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In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds. | 1982 Jan |
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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 Sep |
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In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds. | 1984 Jun |
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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 Aug |
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Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus. | 1985 Jun |
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Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines. | 1985 May |
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In vitro and in vivo antiviral activity of 2'-fluorinated arabinosides of 5-(2-haloalkyl)uracil. | 1987 Jun |
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Novel acyclic adenosine analogs inhibit Epstein-Barr virus replication. | 1987 Sep |
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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 Jul |
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Phosphonoformate and phosphonoacetate derivatives of 5-substituted 2'-deoxyuridines: synthesis and antiviral activity. | 1988 Sep |
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Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines. | 1992 Aug 21 |
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Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. | 1995 Dec |
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Understanding the binding of 5-substituted 2'-deoxyuridine substrates to thymidine kinase of herpes simplex virus type-1. | 1996 Nov 22 |
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Antiviral efficacies of famciclovir, valaciclovir, and brivudin in disseminated herpes simplex virus type 1 infection in mice. | 1997 |
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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 Aug |
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Efficacy of select antivirals against Cryptosporidium parvum in vitro. | 1998 Nov 1 |
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Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
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A rapid phenotypic assay for detection of acyclovir-resistant varicella-zoster virus with mutations in the thymidine kinase open reading frame. | 2000 Apr |
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The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. | 2000 Feb 24 |
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Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
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Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes. | 2000 Oct 15 |
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Novel carbocyclic nucleosides containing a cyclobutyl ring: adenosine analogues. | 2001 Sep |
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A thymidine phosphorylase-stable analogue of BVDU with significant antiviral activity. | 2002 Dec 5 |
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Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides. | 2002 Jul 18 |
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Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase. | 2002 May |
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Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans. | 2003 Aug 4 |
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Amino acid changes within conserved region III of the herpes simplex virus and human cytomegalovirus DNA polymerases confer resistance to 4-oxo-dihydroquinolines, a novel class of herpesvirus antiviral agents. | 2003 Feb |
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Enzymatic and structural analysis of inhibitors designed against Mycobacterium tuberculosis thymidylate kinase. New insights into the phosphoryl transfer mechanism. | 2003 Feb 14 |
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In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
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Evaluation of antiviral activity against human herpesvirus 8 (HHV-8) and Epstein-Barr virus (EBV) by a quantitative real-time PCR assay. | 2004 Jun |
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In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir? | 2004 Mar |
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Human herpesvirus 6 DNA polymerase: enzymatic parameters, sensitivity to ganciclovir and determination of the role of the A961V mutation in HHV-6 ganciclovir resistance. | 2004 Oct |
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Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides. | 2005 Dec 15 |
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Antiadenovirus activities of several classes of nucleoside and nucleotide analogues. | 2005 Mar |
|
Synthesis of some new benzisothiazolone and benzenesulfonamide derivatives of biological interest starting from saccharin sodium. | 2013 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7561799
Brivudin was given as one 125-mg tablet every 6 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21833720
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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Classification Tree | Code System | Code | ||
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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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NCI_THESAURUS |
C1557
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WHO-VATC |
QJ05AB15
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CHEMBL31634
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100000088646
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6267
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69304-47-8
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397
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SUB05893MIG
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C67088
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DB03312
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446727
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633770
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m2655
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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