ContaminantDB: Bromodeoxyuridine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:36 UTC

Update Date

2026-05-14 19:16:14 UTC

Accession Number

CHEM001532

Identification

Common Name

Bromodeoxyuridine

Class

Small Molecule

Description

Bromodeoxyuridine is an organobromide compound and a synthetic nucleoside that is an analogue of thymidine. It is brominated derivative of deoxyuridine that acts as an antimetabolite or base analog, substituting for thymidine in DNA. It can induce DNA mutations in the same way as 2-aminopurine It is used in the detection of proliferating cells in living tissues, as it can be incorporated into the newly synthesized DNA of replicating cells, then detected using antibodies.

Contaminant Sources

T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Bromide Compound
Ether
Industrial/Workplace Toxin
Lachrymator
Organic Compound
Organobromide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
BrdU	MeSH
5 Bromodeoxyuridine	MeSH
Broxuridine	MeSH
5 Bromo 2' deoxyuridine	MeSH
Deoxyriboside, bromouracil	MeSH
Bromouracil deoxyriboside	MeSH
BUdR	MeSH
5-Bromodeoxyuridine	MeSH
5-Bromo-2'-deoxyuridine	MeSH

Chemical Formula

C₉H₁₁BrN₂O₅

Average Molecular Mass

307.098 g/mol

Monoisotopic Mass

305.985 g/mol

CAS Registry Number

59-14-3

IUPAC Name

5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

bromodeoxyuridine

SMILES

OCC1OC(CC1O)N1C=C(Br)C(=O)NC1=O

InChI Identifier

InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)

InChI Key

WOVKYSAHUYNSMH-UHFFFAOYSA-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
Halopyrimidine
Pyrimidone
Aryl bromide
Aryl halide
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Lactam
Urea
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

antimetabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystalline powder.

Experimental Properties

Property	Value
Melting Point	192.5°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	20.4 g/L	ALOGPS
logP	-0.97	ALOGPS
logP	-0.69	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.04	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	2	ChemAxon
Refractivity	58.66 m³·mol⁻¹	ChemAxon
Polarizability	24.25 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-e04750766b00074474a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-925d1ff97208ed0b090a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-dcdaef26976b4e3f0d28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fkc-6893000000-7763fd70cf78db8f47c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01p9-1790000000-1bcddc7af9f495105a1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-e563b0f6f839d4f9148a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

5-bromodeoxyuridine acts on DNA. It induces a random DNA point mutation via base substitution. The base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles. As a thymine analog, 5-bromodeoxyuridine normally pairs with adenine.

Metabolism

5-bromodeoxyuridine is phosphorylated by thymidine kinase to produce 5-bromodeoxyuridine-phosphate. (1)

Toxicity Values

LD50: 2500 mg/kg (Intravenous, Mouse) (3) LD50: 3500 mg/kg (Subcutaneous, Mouse) (3) LD50: 3050 mg/kg (Intraperitoneal, Mouse) (3) LD50: 9100 mg/kg (Oral, Mouse) (3)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. May cause heritable genetic damage.

Uses/Sources

Laboratory chemical used as a mutagen in mutagenesis experiments. It is more commonly used in the detection of proliferating cells in living tissues.

Minimum Risk Level

Not Available

Health Effects

5-bromodeoxyuridine is a mutagen (causes mutations), a cytotoxin, a teratogen and a weak carcinogen. The primary harmful effects are genetic mutation, anemia, reproductive disorders (fetal death or abnormality), cataracts, and skin irritation. It can cause respiratory tract irritation if inhaled, skin irritation if it contacts the skin and eye irritation if it contacts the eyes. As a reproductive toxin BrDU would be considered a “particularly hazardous substance” under the OSHA lab standard.

Symptoms

5-bromodeoxyuridine can cause hypermotility, diarrhea, weight loss and possibly death if large amounts are repeatedly ingested.

Treatment

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

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

Bromodeoxyuridine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

236184

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

Bromodeoxyuridine (CHEM001532)

Structure for CHEM001532: Bromodeoxyuridine