457442
(E)-5-(2-Bromovinyl)uracil
97%
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About This Item
Empirical Formula (Hill Notation):
C6H5BrN2O2
CAS Number:
Molecular Weight:
217.02
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Assay:
97%
Form:
solid
assay
97%
form
solid
InChI
1S/C6H5BrN2O2/c7-2-1-4-3-8-6(11)9-5(4)10/h1-3H,(H2,8,9,10,11)/b2-1+
SMILES string
Br\C=C\C1=CNC(=O)NC1=O
InChI key
BLXGZIDBSXVMLU-OWOJBTEDSA-N
mp
189-194 °C (dec.) (lit.)
functional group
bromo
Storage Class
13 - Non Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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J Yan et al.
Clinical pharmacology and therapeutics, 61(5), 563-573 (1997-05-01)
Bromovinyl-uracil (BVU) is the principal metabolite of sorivudine, a potent anti-zoster nucleoside. BVU binds to, and irreversibly inhibits, the enzyme dihydropyrimidine dehydrogenase (DPD). The objective of this study was to assess the time course of recovery of DPD activity after
T Nishiyama et al.
Molecular pharmacology, 57(5), 899-905 (2000-04-25)
Purified recombinant human dihydropyrimidine dehydrogenase (hDPD) was incubated with (14)C-labeled (E)-5-(2-bromovinyl)uracil ([(14)C]BVU) in the presence of NADPH to investigate a possible mechanism in the 18 patient deaths caused by interactions of 5-fluorouracil prodrugs with the new oral antiviral drug, sorivudine.
S I Kanamitsu et al.
Drug metabolism and disposition: the biological fate of chemicals, 28(4), 467-474 (2000-03-22)
The fatal drug-drug interaction between sorivudine, an antiviral drug, and 5-fluorouracil (5-FU) has been shown to be caused by a mechanism-based inhibition. In this interaction, sorivudine is converted by gut flora to (E)-5-(2-bromovinyl)uracil (BVU), which is metabolically activated by dihydropyrimidine
A S Jones et al.
Journal of medicinal chemistry, 24(6), 759-760 (1981-06-01)
(Z)-5-(2-Bromovinyl)uracil was obtained by photoisomerization of the E. isomer. Similarly, (E)-5-(2-bromovinyl)-2'-deoxyuridine gave the required Z isomer. (Z)-5-(2-Bromovinyl)-2'-deoxyuridine is much less active against herpes simplex virus type 1 (HSV-1) and somewhat less active against herpes simplex virus type 2 than is
H Okuda et al.
The Journal of pharmacology and experimental therapeutics, 287(2), 791-799 (1998-11-10)
A toxicokinetic study was performed using rats to investigate the possible mechanism of 18 acute deaths in Japanese patients with cancer and herpes zoster by interactions of the new oral antiviral drug, sorivudine (SRV), with one of the oral 5-fluorouracil
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