Brivudine

Identification

Name
Brivudine
Accession Number
DB03312
Description

Brivudine is used in the treatment of herpes zoster. Although not approved in the U.S. or Canada, it is approved in several European countries.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 333.135
Monoisotopic: 332.000784183
Chemical Formula
C11H13BrN2O5
Synonyms
  • (E)-5-(2-Bromovinyl)-deoxyuridine
  • Brivudina
  • Brivudine
  • Brivudinum
  • BVdU
External IDs
  • RP-101
  • RP101

Pharmacology

Pharmacology
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Indication
Not Available
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AThymidine kinase 2, mitochondrial
substrate
Humans
ADNA polymerase
inhibitor
Human herpesvirus 1
UThymidine kinase
substrate
Feline herpesvirus 1
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Brivudine.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Brivudine.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Brivudine.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Brivudine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Brivudine.
CapecitabineThe risk or severity of adverse effects can be increased when Brivudine is combined with Capecitabine.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Brivudine.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Brivudine.
Typhoid Vaccine LiveThe therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Brivudine.
Varicella zoster vaccine (live/attenuated)The therapeutic efficacy of Varicella Zoster Vaccine (Live/attenuated) can be decreased when used in combination with Brivudine.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Brivir / Mevir / Zostex

Categories

ATC Codes
J05AB15 — Brivudine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2'-deoxyribonucleosides
Direct Parent
Pyrimidine 2'-deoxyribonucleosides
Alternative Parents
Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Ureas / Lactams / Secondary alcohols / Bromoalkenes / Azacyclic compounds
show 8 more
Substituents
Alcohol / Aromatic heteromonocyclic compound / Azacycle / Bromoalkene / Haloalkene / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
2M3055079H
CAS number
69304-47-8
InChI Key
ODZBBRURCPAEIQ-PIXDULNESA-N
InChI
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
IUPAC Name
5-[(1E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(\C=C\Br)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
446727
PubChem Substance
46505721
ChemSpider
394011
RxNav
59161
ChEMBL
CHEMBL31634
ZINC
ZINC000003653378
PDBe Ligand
BVD
Wikipedia
Brivudine
PDB Entries
1ki8 / 2vqs

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentDry Eye Syndromes1
2TerminatedHealth Services ResearchMalignant Neoplasm of Pancreas1
1, 2Unknown StatusTreatmentColorectal Cancers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral125 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-0.5ChemAxon
pKa (Strongest Acidic)9.74ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.1 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity67.68 m3·mol-1ChemAxon
Polarizability27.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9902
Blood Brain Barrier+0.7736
Caco-2 permeable-0.8605
P-glycoprotein substrateNon-substrate0.7193
P-glycoprotein inhibitor INon-inhibitor0.8475
P-glycoprotein inhibitor IINon-inhibitor0.7567
Renal organic cation transporterNon-inhibitor0.8965
CYP450 2C9 substrateNon-substrate0.7267
CYP450 2D6 substrateNon-substrate0.8629
CYP450 3A4 substrateNon-substrate0.5327
CYP450 1A2 substrateNon-inhibitor0.9012
CYP450 2C9 inhibitorNon-inhibitor0.9144
CYP450 2D6 inhibitorNon-inhibitor0.9322
CYP450 2C19 inhibitorNon-inhibitor0.9104
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8914
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7862
BiodegradationNot ready biodegradable0.8546
Rat acute toxicity1.8200 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9469
hERG inhibition (predictor II)Non-inhibitor0.8723
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Thymidine kinase activity
Specific Function
Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
Gene Name
TK2
Uniprot ID
O00142
Uniprot Name
Thymidine kinase 2, mitochondrial
Molecular Weight
31004.53 Da
References
  1. Franzolin E, Rampazzo C, Perez-Perez MJ, Hernandez AI, Balzarini J, Bianchi V: Bromovinyl-deoxyuridine: A selective substrate for mitochondrial thymidine kinase in cell extracts. Biochem Biophys Res Commun. 2006 May 26;344(1):30-6. doi: 10.1016/j.bbrc.2006.03.147. [PubMed:16630572]
Kind
Protein
Organism
Human herpesvirus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
3'-5' exonuclease activity
Gene Name
DNApol
Uniprot ID
Q91CQ6
Uniprot Name
DNA polymerase
Molecular Weight
136474.73 Da
References
  1. Rabasseda X: Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs Today (Barc). 2003 May;39(5):359-71. doi: 10.1358/dot.2003.39.5.740221. [PubMed:12861349]
Kind
Protein
Organism
Feline herpesvirus 1
Pharmacological action
Unknown
Actions
Substrate
General Function
Catalyzes the transfer of the gamma-phospho group of ATP to thymidine to generate dTMP in the salvage pathway of pyrimidine synthesis. The dTMP serves as a substrate for DNA polymerase during viral DNA replication. Allows the virus to be reactivated and to grow in non-proliferative cells lacking a high concentration of phosphorylated nucleic acid precursors.
Specific Function
Atp binding
Gene Name
TK
Uniprot ID
P13159
Uniprot Name
Thymidine kinase
Molecular Weight
38922.3 Da
References
  1. Solaroli N, Johansson M, Persoons L, Balzarini J, Karlsson A: Substrate specificity of feline and canine herpesvirus thymidine kinase. Antiviral Res. 2008 Aug;79(2):128-32. doi: 10.1016/j.antiviral.2008.03.003. Epub 2008 Apr 14. [PubMed:18455811]

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51