Structure via PubChem · Public domain (PubChem)
bromodeoxyuridine
Sign in to saveAlso known as BrdU, Bromouracil deoxyriboside, 5-Bromouracil-2-deoxyriboside, 5-Bromouracil deoxyriboside, 5-Bromodesoxyuridine, 5-Bdu, 5-Bromodeoxyuridine, Broxuridine
Bromodeoxyuridine ('''5-bromo-2'-deoxyuridine, BrdU, BUdR, BrdUrd, broxuridine''') is a synthetic nucleoside analogue with a chemical structure similar to thymidine. BrdU is commonly used to study cell proliferation in living tissues and has been studied as a radiosensitizer and diagnostic tool in people with cancer.
Chemical data
- Formula
- C9H11BrN2O5
- Molecular weight
- 307.1 g/mol
- IUPAC name
- 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Br)CO)O
- InChIKey
- WOVKYSAHUYNSMH-RRKCRQDMSA-N
- XLogP
- -0.3
- Polar surface area
- 99.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- leukemia, prostate cancer
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- bromine
- Mass
- 305.985
Show 6 more facts
- subject has role
- radiosensitizer
- chemical formula
- C₉H₁₁BrN₂O₅
- canonical SMILES
- C1C(C(OC1N2C=C(C(=O)NC2=O)Br)CO)O
- isomeric SMILES
- C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Br)CO)O
- World Health Organisation international non-proprietary name
- broxuridine
- Commons category
- Bromodeoxyuridine
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Bromodeoxyuridine ('''5-bromo-2'-deoxyuridine, BrdU, BUdR, BrdUrd, broxuridine') is a synthetic nucleoside analogue with a chemical structure similar to thymidine. BrdU is commonly used to study cell proliferation in living tissues and has been studied as a radiosensitizer and diagnostic tool in people with cancer.
During the S phase of the cell cycle (when DNA replication occurs), BrdU can be incorporated in place of thymidine in newly synthesized DNA molecules of dividing cells. Cells that have recently performed DNA replication or DNA repair can be detected with antibodies specific for BrdU using techniques such as immunohistochemistry or immunofluorescence. BrdU-labelled cells in humans can be detected up to two years after BrdU infusion.
Excerpted from Wikipedia’s “bromodeoxyuridine” article, available under the CC BY-SA 4.0 licence.