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
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 |
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 |
---|---|---|---|
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 |
---|---|---|---|---|
Primary | Brivox Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
(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 |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:59:20 GMT 2023
by
admin
on
Sat Dec 16 15:59:20 GMT 2023
|
Record UNII |
2M3055079H
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
100000088646
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 | |||
|
6267
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 | |||
|
69304-47-8
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 | |||
|
397
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 | |||
|
SUB05893MIG
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 | |||
|
C67088
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 | |||
|
DB03312
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 | |||
|
446727
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 | |||
|
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 | |||
|
m2655
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 | ||
|
59161
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 | RxNorm | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |