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457442

Sigma-Aldrich

(E)-5-(2-Bromovinyl)uracil

97%

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About This Item

Empirical Formula (Hill Notation):
C6H5BrN2O2
CAS Number:
Molecular Weight:
217.02
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

97%

form

solid

mp

189-194 °C (dec.) (lit.)

functional group

bromo

SMILES string

Br\C=C\C1=CNC(=O)NC1=O

InChI

1S/C6H5BrN2O2/c7-2-1-4-3-8-6(11)9-5(4)10/h1-3H,(H2,8,9,10,11)/b2-1+

InChI key

BLXGZIDBSXVMLU-OWOJBTEDSA-N

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Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
Jan Balzarini et al.
Molecular pharmacology, 61(5), 1140-1145 (2002-04-19)
The susceptibility of the bicyclic nucleoside analogs (BCNAs), highly potent and selective inhibitors of varicella-zoster virus (VZV), to the enzymes involved in nucleoside/nucleobase catabolism has been investigated in comparison with the established anti-VZV agent (E)-5-(2-bromovinyl)-2'-deoxyuridine [BVDU; brivudine (Zostex)]. Whereas human
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 Nakayama et al.
Pharmacogenetics, 7(1), 35-43 (1997-02-01)
Sorivudine, 1-beta-D-arabinofuranosyl-5-(E)-(2-bromovinyl)uracil, is a potent antiviral agent against varicella-zoster virus and herpes simplex virus type 1. However, sorivudine should not be used in combination with anticancer drugs such as 5-fluorouracil (5-FU) because (E)-5-(2-bromovinyl)uracil (BVU), a metabolite of sorivudine, inhibits the
D B Whigan et al.
Journal of chromatography. B, Biomedical applications, 664(2), 357-363 (1995-02-17)
This paper describes the determination of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil in urine. The method involves sample clean-up by liquid-liquid extraction with ethyl acetate followed by high-performance liquid chromatographic (HPLC) analysis. The sample preparation may be performed either manually or automatically using a Zymark

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