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Chemical Compound Review

GCQYYIHYQMVWLT-BDNRQGISSA-N     5-(2-bromoethenyl)-1- [(2R,3S,4R,5R)-3,4...

Synonyms:
 
 
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Disease relevance of D01734

 

High impact information on D01734

 

Chemical compound and disease context of D01734

 

Biological context of D01734

 

Associations of D01734 with other chemical compounds

  • They can also be wanted (eg, use of ciclosporin to enhance the oral bioavailability of paclitaxel); unwanted (eg, combination of the antiviral agent sorivudine and oral fluorouracil analogues can lead to fatal complications); between cytotoxic drugs, cytotoxic drugs and non-cytotoxic drugs; or with pharmaceutical vehicles [13].
 

Analytical, diagnostic and therapeutic context of D01734

  • These findings suggest that antiherpesviral 5-substituted araU analogues can be relatively stable in vivo, when injected intravenously, and that degradation of 1-beta-D-arabinofuranosyl-5-(E-2-bromovinyl)uracil (sorivudine) following oral administration is due primarily to the action of enterobacteria [14].
  • More than a dozen cancer patients died in 1993 after treatment with antineoplastic derivatives of 5-fluorouracil and the antiherpes drug Sorivudine [15].

References

  1. The effect of sorivudine on dihydropyrimidine dehydrogenase activity in patients with acute herpes zoster. Yan, J., Tyring, S.K., McCrary, M.M., Lee, P.C., Haworth, S., Raymond, R., Olsen, S.J., Diasio, R.B. Clin. Pharmacol. Ther. (1997) [Pubmed]
  2. Sorivudine: a promising drug for the treatment of varicella-zoster virus infection. Whitley, R.J. Neurology (1995) [Pubmed]
  3. Treatment of adult varicella with sorivudine: a randomized, placebo-controlled trial. Wallace, M.R., Chamberlin, C.J., Sawyer, M.H., Arvin, A.M., Harkins, J., LaRocco, A., Colopy, M.W., Bowler, W.A., Oldfield, E.C. J. Infect. Dis. (1996) [Pubmed]
  4. Intestinal anaerobic bacteria hydrolyse sorivudine, producing the high blood concentration of 5-(E)-(2-bromovinyl)uracil that increases the level and toxicity of 5-fluorouracil. Nakayama, H., Kinouchi, T., Kataoka, K., Akimoto, S., Matsuda, Y., Ohnishi, Y. Pharmacogenetics (1997) [Pubmed]
  5. Sorivudine versus acyclovir for treatment of dermatomal herpes zoster in human immunodeficiency virus-infected patients: results from a randomized, controlled clinical trial. Collaborative Antiviral Study Group/AIDS Clinical Trials Group, Herpes Zoster Study Group. Gnann, J.W., Crumpacker, C.S., Lalezari, J.P., Smith, J.A., Tyring, S.K., Baum, K.F., Borucki, M.J., Joseph, W.P., Mertz, G.J., Steigbigel, R.T., Cloud, G.A., Soong, S.J., Sherrill, L.C., DeHertogh, D.A., Whitley, R.J. Antimicrob. Agents Chemother. (1998) [Pubmed]
  6. Mechanism-based inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil in the presence of NADPH. Nishiyama, T., Ogura, K., Okuda, H., Suda, K., Kato, A., Watabe, T. Mol. Pharmacol. (2000) [Pubmed]
  7. The Epstein-Barr virus thymidine kinase does not phosphorylate ganciclovir or acyclovir and demonstrates a narrow substrate specificity compared to the herpes simplex virus type 1 thymidine kinase. Gustafson, E.A., Chillemi, A.C., Sage, D.R., Fingeroth, J.D. Antimicrob. Agents Chemother. (1998) [Pubmed]
  8. Evaluation of sorivudine (BV-araU) versus acyclovir in the treatment of acute localized herpes zoster in human immunodeficiency virus-infected adults. The Multinational Sorivudine Study Group. Bodsworth, N.J., Boag, F., Burdge, D., Généreux, M., Borleffs, J.C., Evans, B.A., Modai, J., Colebunders, R., Thomas, M., DeHertogh, D., Pacelli, L., Thomis, J. J. Infect. Dis. (1997) [Pubmed]
  9. Antiviral therapy of herpes simplex and varicella-zoster virus infections. Wutzler, P. Intervirology (1997) [Pubmed]
  10. Lethal drug interactions of sorivudine, a new antiviral drug, with oral 5-fluorouracil prodrugs. Okuda, H., Nishiyama, T., Ogura, K., Nagayama, S., Ikeda, K., Yamaguchi, S., Nakamura, Y., Kawaguchi, Y., Watabe, T. Drug Metab. Dispos. (1997) [Pubmed]
  11. Effects of light intensity, n-alcohols, water-soluble colorants, and solution viscosity on photoisomerization of sorivudine. Desai, D., Li, D., Janjikhel, R., Lang, B., Jain, N. Pharmaceutical development and technology. (2001) [Pubmed]
  12. Sorivudine: a potent inhibitor of varicella zoster virus replication. Whitley, R.J. Adv. Exp. Med. Biol. (1996) [Pubmed]
  13. Drug interactions in oncology. Beijnen, J.H., Schellens, J.H. The lancet oncology. (2004) [Pubmed]
  14. Deglycosylation of antiherpesviral 5-substituted arabinosyluracil derivatives by rat liver extract and enterobacteria cells. Machida, H., Watanabe, Y., Kano, F., Sakata, S., Kumagai, M., Yamaguchi, T. Biochem. Pharmacol. (1995) [Pubmed]
  15. Apoptosis by antitumor agents and other factors in relation to cell cycle checkpoints. Kondo, S. J. Radiat. Res. (1995) [Pubmed]
 
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