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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:

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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 Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
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
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

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