A pyrimidine base
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Parent Compound(s)
29448Brivudine
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(E)-5-(2-Bromovinyl)uracil

Item No. 21030

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(1E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione
CAS Number
69304-49-0
Synonyms
  • BVU
Molecular Formula
C6H5BrN2O2
Formula Weight
217.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 60 mg/mLDMSO: 53 mg/mLEthanol: 0.8 mg/mLPBS (pH 7.2): 8 mg/mL
λmax
250, 290 nm
SMILES
O=C1NC(NC=C1/C=C/Br)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 mg

    $70

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    50 mg

    $117

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    100 mg

    $215

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    250 mg

    $329

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    Product Description

    (E)-5-(2-Bromovinyl)uracil (BVU) is a pyrimidine base and an inactive metabolite of the antiviral agents sorivudine and (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) that may be regenerated to BVDU in vivo.1,2,3 BVU irreversibly inactivates dihydropyrimidine dehydrogenase (DPD) in an NADPH-dependent manner.1,4 It enhances the efficacy of the chemotherapeutic agent and DPD substrate 5-fluorouracil (5-FU; Item No. 14416) in a P388 murine leukemia model when administered at a dose of 200 µmol/kg, increasing survival time.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ogura, K., Nishiyama, T., Takubo, H., et al. Suicidal inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil derived from the antiviral, sorivudine. Cancer Lett. 122(1-2), 107-113 (1998).

    2. Desgranges, C., Razaka, G., Drouiller, F., et al. Regeneration of the antiviral drug (E)-5-(2-bromovinyl)-2′-deoxyuridine in vivo. Nucleic Acids Res. 12(4), 2081-2110 (1984).

    3. De Clercq, E., Desgranges, C., Herdewijn, P., et al. Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine. J. Med. Chem. 29(2), 213-217 (1986).

    4. Desgranges, C., Razaka, G., De Clercq, E., et al. Effect of (E)-5-(2-bromovinyl)uracil on the catabolism and antitumor activity of 5-fluorouracil in rats and leukemic mice. Cancer Res. 46(3), 1094-1101 (1986).