Brivudine

Identification

Name
Brivudine
Accession Number
DB03312  (EXPT00783)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Brivudina
External IDs
RP-101 / RP101
International/Other Brands
Zostex
Categories
UNII
2M3055079H
CAS number
69304-47-8
Weight
Average: 333.135
Monoisotopic: 332.000784183
Chemical Formula
C11H13BrN2O5
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-[(E)-2-bromoethenyl]-4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
SMILES
[H]\C(Br)=C(\[H])C1=CN(C(=O)N=C1O)[C@@]1([H])C[C@]([H])(O)[C@@]([H])(CO)O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidine kinaseNot AvailableHHV-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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Influenza a virus a/california/7/2009 (h1n1) live (attenuated) antigenThe therapeutic efficacy of Influenza a virus a/california/7/2009 (h1n1) live (attenuated) antigen can be decreased when used in combination with Brivudine.
Influenza a virus a/perth/16/2009 (h3n2) live (attenuated) antigenThe therapeutic efficacy of Influenza a virus a/perth/16/2009 (h3n2) live (attenuated) antigen can be decreased when used in combination with Brivudine.
Influenza Vaccine (Live/Attenuated)The therapeutic efficacy of Brivudine can be decreased when used in combination with Influenza Vaccine (Live/Attenuated).
Varicella Zoster Vaccine (Live/Attenuated)The therapeutic efficacy of Varicella Zoster Vaccine (Live/Attenuated) can be decreased when used in combination with Brivudine.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
446727
PubChem Substance
46505721
ChemSpider
394011
ChEMBL
CHEMBL31634
HET
BVD
Wikipedia
Brivudine
ATC Codes
J05AB15 — Brivudine
PDB Entries
1ki8 / 2vqs

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.48 mg/mLALOGPS
logP-0.61ALOGPS
logP-0.13ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.54ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area102.59 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68 m3·mol-1ChemAxon
Polarizability27.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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

Taxonomy

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
Pyrimidine 2'-deoxyribonucleoside / Pyrimidone / Hydropyrimidine / Pyrimidine / Heteroaromatic compound / Tetrahydrofuran / Vinylogous amide / Lactam / Secondary alcohol / Urea
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
HHV-1
Pharmacological action
Unknown
General Function
Thymidine kinase activity
Specific Function
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
Gene Name
TK
Uniprot ID
P03176
Uniprot Name
Thymidine kinase
Molecular Weight
40971.555 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 05, 2018 17:48