Brivudine
Star1
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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Herpes zoster •••••••••••• •••••• Treatment of Shingles •••••••••••• •••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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. View sample adverse effects data in our new Data Library!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. - 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 splash10-014j-9565000000-25350be2aff060da0cc5 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-1095000000-9ab3d3a55df66cf825df Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00xs-1940000000-248fcb6918ed25e34f83 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01p2-1950000000-5da3cb12494d19cc18c3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014v-1590000000-82f96708d11e8991474c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-6950000000-a0c5ae2f1a1f5be3856f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.00006 predictedDeepCCS 1.0 (2019) [M+H]+ 164.39561 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.69737 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsThymidine kinase 2, mitochondrial
- 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]
2. DetailsDNA polymerase
- 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]
3. DetailsThymidine kinase
- 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