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Chemical Compound Review:

BV uracil 5-[(E)-2-bromoethenyl]-1H- pyrimidine-2,4...

Synonyms: CHEMBL68200, AC1LELS0, CCRIS 5284, AG-G-69466, KB-02514, ...

Kanamitsu, S.I. et al., Onishi, T. et al., Ogura, K. et al., Nishiyama, T. et al.

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High impact information on BV uracil

Mechanism-based inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil in the presence of NADPH [1].
It showed good oral bioavailability in rats (68.5%) and, unlike (E)-5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil (BVaraU), did not result in the release of (E)-5-(2-bromovinyl)uracil (BVU), a potent dihydropyrimidine dehydrogenase inhibitor, in plasma after oral administration [2].
Prediction of in vivo drug-drug interactions based on mechanism-based inhibition from in vitro data: inhibition of 5-fluorouracil metabolism by (E)-5-(2-Bromovinyl)uracil [3].
Suicidal inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil derived from the antiviral, sorivudine [4].

Associations of BV uracil with other chemical compounds

In this interaction, sorivudine is converted by gut flora to (E)-5-(2-bromovinyl)uracil (BVU), which is metabolically activated by dihydropyrimidine dehydrogenase (DPD), and the activated BVU irreversibly binds to DPD itself, thereby inactivating it [3].

References

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]
Synthesis and antiviral activity of novel anti-VZV 5-substituted uracil nucleosides with a cyclopropane sugar moiety. Onishi, T., Mukai, C., Nakagawa, R., Sekiyama, T., Aoki, M., Suzuki, K., Nakazawa, H., Ono, N., Ohmura, Y., Iwayama, S., Okunishi, M., Tsuji, T. J. Med. Chem. (2000) [Pubmed]
Prediction of in vivo drug-drug interactions based on mechanism-based inhibition from in vitro data: inhibition of 5-fluorouracil metabolism by (E)-5-(2-Bromovinyl)uracil. Kanamitsu, S.I., Ito, K., Okuda, H., Ogura, K., Watabe, T., Muro, K., Sugiyama, Y. Drug Metab. Dispos. (2000) [Pubmed]
Suicidal inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil derived from the antiviral, sorivudine. Ogura, K., Nishiyama, T., Takubo, H., Kato, A., Okuda, H., Arakawa, K., Fukushima, M., Nagayama, S., Kawaguchi, Y., Watabe, T. Cancer Lett. (1998) [Pubmed]

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