Brivudine

Title: Brivudine
CAS Registry Number: 69304-47-8
CAS Name: 5-[(1E)-2-Bromoethenyl]-2¢-deoxyuridine
Additional Names: (E)-5-(2-bromovinyl)-2¢-deoxyuridine; brivudin; BVDU
Trademarks: Brivex (Menarini); Brivirac (Menarini); Nervinex (Menarini); Zecovir (Guidotti); Zostex (Berlin-Chemie)
Molecular Formula: C11H13BrN2O5
Molecular Weight: 333.14
Percent Composition: C 39.66%, H 3.93%, Br 23.99%, N 8.41%, O 24.01%
Literature 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. Olgemöller 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).
Properties: White needles from methanol-water, mp 123-125° (dec). uv max: 253, 295 nm (e 13100, 10300).
Melting point: mp 123-125°
Absorption maximum: uv max: 253, 295 nm (e 13100, 10300)
Therap-Cat: Antiviral.
Keywords: Antiviral; Purines/Pyrimidinones.
Brodimoprim Bromacil Bromadiolone Bromal Bromal Hydrate

Brivudine
Brivudine - Brivudin.svg
Systematic (IUPAC) name
5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat. exclusion
Legal status  ?
Routes oral
Pharmacokinetic data
Bioavailability 30%
Half-life 16 hours
Excretion mainly renal
Identifiers
CAS number 69304-47-8 N
ATC code J05AB15
PubChem CID 446727
ChemSpider 394011 YesY
UNII 2M3055079H YesY
ChEMBL CHEMBL31634 YesY
Chemical data
Formula C11H13BrN2O5 
Mol. mass 333.135 g/mol
 N (what is this?)  (verify)

Brivudine is an antiviral drug used in the treatment of herpes zoster.