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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
Structure of BRIVUDINE

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

HIDE SMILES / InChI

Molecular Formula C11H13BrN2O5
Molecular Weight 333.135
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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

Sources: Zeitschrift fuer die Gesamte Experimentelle Medizin (1925), 47, 211-21.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
240.0 nM [Ki]
29.0 µM [EC50]
80.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Brivox

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
(E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent.
1979 Jun
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
(E)-5-(2-bromovinyl)-2'-Deoxyuridine in the treatment of experimental herpes simplex keratitis.
1980 Jan
Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils.
1981 Jul
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases.
1981 Sep
In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds.
1982 Jan
Oral antiviral drugs in experimental herpes simplex keratitis.
1983 Dec
Efficacy and selectivity of some nucleoside analogs as anti-human cytomegalovirus agents.
1983 Oct
Comparative efficacy and selectivity of some nucleoside analogs against Epstein-Barr virus.
1985 Jun
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.
1985 May
Inhibiting effect of (RS)-9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine on varicella-zoster virus replication in cell culture.
1987 Jan
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
Phosphonoformate and phosphonoacetate derivatives of 5-substituted 2'-deoxyuridines: synthesis and antiviral activity.
1988 Sep
The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogues.
1991 Sep
Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines.
1992 Aug 21
(+-)-carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties.
1992 Jun 12
Synthesis and antiherpes virus activity of 1,5-anhydrohexitol nucleosides.
1993 Jul 9
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
Antiviral efficacies of famciclovir, valaciclovir, and brivudin in disseminated herpes simplex virus type 1 infection in mice.
1997
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
Efficacy of select antivirals against Cryptosporidium parvum in vitro.
1998 Nov 1
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Phenotypic and genetic characterization of thymidine kinase from clinical strains of varicella-zoster virus resistant to acyclovir.
1999 Oct
A rapid phenotypic assay for detection of acyclovir-resistant varicella-zoster virus with mutations in the thymidine kinase open reading frame.
2000 Apr
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
2000 Dec 28
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes.
2000 Oct 15
Synthesis of 1-(2-deoxy-beta-D-ribofuranosyl)-2,4-difluoro-5-substituted-benzene thymidine mimics, some related alpha-anomers, and their evaluation as antiviral and anticancer agents.
2001 Jan-Feb
Potent in vivo antiviral activity of the herpes simplex virus primase-helicase inhibitor BAY 57-1293.
2002 Jun
Comparative study of purine and pyrimidine nucleoside analogues acting on the thymidylate kinases of Mycobacterium tuberculosis and of humans.
2003 Aug 4
Enzymatic and structural analysis of inhibitors designed against Mycobacterium tuberculosis thymidylate kinase. New insights into the phosphoryl transfer mechanism.
2003 Feb 14
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Evaluation of antiviral activity against human herpesvirus 8 (HHV-8) and Epstein-Barr virus (EBV) by a quantitative real-time PCR assay.
2004 Jun
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?
2004 Mar
Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides.
2005 Dec 15
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.
2005 Mar
Antiadenovirus activities of several classes of nucleoside and nucleotide analogues.
2005 Mar
Structural studies of nucleoside analog and feedback inhibitor binding to Drosophila melanogaster multisubstrate deoxyribonucleoside kinase.
2008 May
Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): part II.
2008 Nov 1
4-Benzyloxy-gamma-sultone derivatives: discovery of a novel family of non-nucleoside inhibitors of human cytomegalovirus and varicella zoster virus.
2009 Mar 26
Synthesis of some new benzisothiazolone and benzenesulfonamide derivatives of biological interest starting from saccharin sodium.
2013 Oct
Patents

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:59:20 GMT 2023
Edited
by admin
on Sat Dec 16 15:59:20 GMT 2023
Record UNII
2M3055079H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRIVUDINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
brivudine [INN]
Common Name English
BRIVUDIN
Common Name English
NSC-633770
Code English
BVDU
Common Name English
BRIVUDINE [MI]
Common Name English
Brivudine [WHO-DD]
Common Name English
BRIVUDINE [MART.]
Common Name English
RP101
Code English
ZOSTEX
Brand Name English
RP-101
Code English
5-((E)-2-BROMOVINYL)-2'-DEOXYURIDINE
Systematic Name English
Classification Tree Code System Code
WHO-ATC J05AB15
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
FDA ORPHAN DRUG 247807
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
NCI_THESAURUS C471
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
EU-Orphan Drug EU/3/09/703
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
NCI_THESAURUS C1557
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
WHO-VATC QJ05AB15
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL31634
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
SMS_ID
100000088646
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PRIMARY
INN
6267
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PRIMARY
CAS
69304-47-8
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PRIMARY
DRUG CENTRAL
397
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PRIMARY
EVMPD
SUB05893MIG
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PRIMARY
NCI_THESAURUS
C67088
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PRIMARY
DRUG BANK
DB03312
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PRIMARY
PUBCHEM
446727
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PRIMARY
NSC
633770
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
MERCK INDEX
m2655
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PRIMARY Merck Index
RXCUI
59161
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PRIMARY RxNorm
MESH
C020235
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
WIKIPEDIA
Brivudine
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID0045755
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
FDA UNII
2M3055079H
Created by admin on Sat Dec 16 15:59:20 GMT 2023 , Edited by admin on Sat Dec 16 15:59:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY