Identification
- Summary
Brivudine is a drug used to treat herpes zoster.
- Generic Name
- Brivudine
- DrugBank Accession Number
- DB03312
- Background
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
Structure for Brivudine (DB03312)
- 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
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AThymidine kinase 2, mitochondrial substrateHumans ADNA polymerase inhibitorHuman herpesvirus 1 UThymidine kinase substrateFeline 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Brivudine. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Brivudine. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Brivudine. Bacillus calmette-guerin substrain russian BCG-I live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Brivudine. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Brivudine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Brivudine. Capecitabine The risk or severity of adverse effects can be increased when Brivudine is combined with Capecitabine. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Brivudine. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Brivudine. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Brivudine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Brivir / Mevir / Zostex
Categories
- ATC Codes
- J05AB15 — Brivudine
- Drug Categories
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Deoxyribonucleosides
- Deoxyuridine
- Direct Acting Antivirals
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors
- Pyrimidine Nucleosides
- Pyrimidines
- 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
- Affected organisms
- 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
- External Links
- PubChem Compound
- 446727
- PubChem Substance
- 46505721
- ChemSpider
- 394011
- 59161
- ChEMBL
- CHEMBL31634
- ZINC
- ZINC000003653378
- PDBe Ligand
- BVD
- Wikipedia
- Brivudine
- PDB Entries
- 1ki8 / 2vqs
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Dry Eye Syndrome (DES) 1 2 Terminated Health Services Research Pancreatic Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 125 mg Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP -0.5 Chemaxon pKa (Strongest Acidic) 9.74 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 99.1 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.68 m3·mol-1 Chemaxon Polarizability 27.9 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9902 Blood Brain Barrier + 0.7736 Caco-2 permeable - 0.8605 P-glycoprotein substrate Non-substrate 0.7193 P-glycoprotein inhibitor I Non-inhibitor 0.8475 P-glycoprotein inhibitor II Non-inhibitor 0.7567 Renal organic cation transporter Non-inhibitor 0.8965 CYP450 2C9 substrate Non-substrate 0.7267 CYP450 2D6 substrate Non-substrate 0.8629 CYP450 3A4 substrate Non-substrate 0.5327 CYP450 1A2 substrate Non-inhibitor 0.9012 CYP450 2C9 inhibitor Non-inhibitor 0.9144 CYP450 2D6 inhibitor Non-inhibitor 0.9322 CYP450 2C19 inhibitor Non-inhibitor 0.9104 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8914 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.7862 Biodegradation Not ready biodegradable 0.8546 Rat acute toxicity 1.8200 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9469 hERG inhibition (predictor II) Non-inhibitor 0.8723
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32