ContaminantDB: Brivudine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:18:39 UTC

Update Date

2026-04-13 22:15:31 UTC

Accession Number

CHEM018526

Identification

Common Name

Brivudine

Class

Small Molecule

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.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Zostex	Kegg
(e)-5-(2-Bromovinyl)-2'-deoxyuridine	MeSH
5-(2-Bromoethenyl)-2'-deoxyuridine	MeSH
5-BVDU	MeSH
Z-5-(2-Bromovinyl)-durd	MeSH
5-(2-Bromovinyl)-2'-deoxyuridine	MeSH
Berlin-chemie brand OF brivudine	MeSH
e-5-(2-Bromovinyl)-durd	MeSH
Brivudin	MeSH
(Z)-5-(2-Bromovinyl)-2'-deoxyuridine	MeSH

Chemical Formula

C₁₁H₁₃BrN₂O₅

Average Molecular Mass

333.135 g/mol

Monoisotopic Mass

332.001 g/mol

CAS Registry Number

69304-47-8

IUPAC Name

5-[(E)-2-bromoethenyl]-4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

Traditional Name

helpin

SMILES

[H]\C(Br)=C(\[H])C1=CN(C(=O)N=C1O)[C@@]1([H])C[C@]([H])(O)[C@@]([H])(CO)O1

InChI Identifier

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

InChI Key

ODZBBRURCPAEIQ-PIXDULNESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides 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

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Vinylogous amide
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Bromoalkene
Vinyl bromide
Vinyl halide
Haloalkene
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organohalogen compound
Organobromide
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.48 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.13	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68 m³·mol⁻¹	ChemAxon
Polarizability	27.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-3af0c7a9743cb8c9e409	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0790000000-b75b367c31a59461deab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0960000000-af2d5aca3d5fb6c08533	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001s-2797000000-1b92c72586a3b5e7660d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-0392000000-5e49696f0cf8f68f5557	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9620000000-913fabaec41be58475e5	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB03312

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Brivudine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

446727

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Brivudine (CHEM018526)

Structure for CHEM018526: Brivudine