1452. Broxuridine

Nomenclature

CAS number: 59-14-3
5-Bromo-2′-deoxyuridine; 5-bromouracil deoxyriboside; BrdUrd; BUdR; NSC-38297; Broxine (NeoPharm); Neomark (NeoPharm); Radibud (Takeda).
C9H11BrN2O5; mol wt 307.10.
C 35.20%, H 3.61%, Br 26.02%, N 9.12%, O 26.05%.

Description and references

Thymidine, q.v., analog. Preferentially incorporated into cellular DNA in place of thymidine during replication causing increased radiosensitivity of the cell. Prepn and inhibition of DNA biosynthesis: R. E. Beltz, D. W. Visser, J. Am. Chem. Soc. 77, 736 (1955); T. J. Bardos et al., ibid. 4279. X-ray crystallography: J. Iball et al., Nature 209, 1230 (1966). HPLC determn in plasma: D. A. Ganes, J. G. Wagner, J. Chromatogr. 432, 233 (1988). Clinical studies in brain tumors: H. S. Greenberg et al., Neurology 44, 1715 (1994); T. L. Phillips et al., Int. J. Radiat. Oncol. Biol. Phys. 21, 709 (1991). Review of radiobiology and therapeutic potential: T. J. Kinsella et al., ibid. 10, 1399-1406 (1984); of genetic toxicology: S. M. Morris, Mutat. Res. 258, 161-188 (1991); of role in management of CNS tumors: A. Freese et al., J. Neuro-Oncol. 20, 81-95 (1994). Series of reviews on diagnostic and research use: F. Dolbeare, Histochem. J. 27, 339-369, 923-964 (1995); 28, 531-575 (1996).

Chemical structure

Properties

Crystals from abs ethanol, mp 187-189° (Beltz, Visser); also reported as mp 181-183° (Bardos). uv max (in HCl): 280 nm (ε 9.9 × 103); uv max (in NaOH): 277 nm (ε 7.2 × 103).

Use

Research tool for measuring DNA synthesis.

Therapeutic Category

Antineoplastic adjunct (radiosensitizer); diagnostic aid (tumor cell label for cytokinetic analysis).

Keywords

Antineoplastic Adjunct; Radiosensitizer; Diagnostic Aid