1378. Brivudine

Nomenclature

CAS number: 69304-47-8
5-[(1E)-2-Bromoethenyl]-2′-deoxyuridine; (E)-5-(2-bromovinyl)-2′-deoxyuridine; brivudin; BVDU; Brivex (Menarini); Brivirac (Menarini); Nervinex (Menarini); Zecovir (Guidotti); Zostex (Berlin-Chemie).
C11H13BrN2O5; mol wt 333.14.
C 39.66%, H 3.93%, Br 23.99%, N 8.41%, O 24.01%.

Description and references

Analog of thymidine, q.v., with selective activity against herpes simplex virus type 1 and varicella-zoster virus. Prepn: A. S. Jones et al., DE 2915254; eidem, US 4424211 (1979, 1984 both to University of Birmingham and Rega Institut); and antiviral activity: E. De Clercq et al, Proc. Natl. Acad. Sci. USA 76, 2947 (1979). Mechanism of action studies: H. S. Allaudeen et al., ibid. 78, 2698 (1981); J. Balzarini, E. De Clercq, Methods Find. Exp. Clin. Pharmacol. 11, 379 (1989). Cytotoxic properties vs viral tumor cells: C. Grignet-Debrus et al., Cancer Gene Ther. 7, 215 (2000). CE determn in plasma and urine: J. Olgemller et al., J. Chromatogr. B 726, 261 (1999). Clinical evaluation in herpetic keratitis: P. C. Maudgal, E. De Clercq, Curr. Eye Res. 10, Suppl., 193 (1991). Clinical comparison with acyclovir, q.v., in herpes zoster: S. W. Wassilew et al., Antiviral Res. 59, 49, 57 (2003). Review of pharmacology and clinical efficacy in herpes zoster: S. J. Keam et al., Drugs 64, 2091-2097 (2004); of antiviral activity, mechanism of action, and clinical efficacy: E. De Clercq, Med. Res. Rev. 25, 1-20 (2005).

Chemical structure

Properties

White needles from methanol-water, mp 123-125° (dec). uv max: 253, 295 nm (ε 13100, 10300).

Therapeutic Category

Antiviral.

Keywords

Antiviral; Nucleosides/Nucleotides