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    Brivudine

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 69304-47-8, Bvdu, (e)-5-(2-bromovinyl)-2'-deoxyuridine, Brivudin, Helpin, Zostex
    Molecular Formula
    C11H13BrN2O5
    Molecular Weight
    333.13  g/mol
    InChI Key
    ODZBBRURCPAEIQ-PIXDULNESA-N
    FDA UNII
    2M3055079H
    Brivudine is a uridine derivative and nucleoside analog with pro-apoptotic and chemosensitizing properties. In vitro, bromovinyl-deoxyuridine (BVDU) has been shown to downregulate the multifunctional DNA repair enzyme APEX nuclease 1, resulting in the inhibition of DNA repair and the induction of apoptosis. In addition, this agent may inhibit the expression of STAT3 (signal transducer and activator of transcription 3), which may result in the downregulation of vascular endothelial growth factor (VEGF). BVDU has also been found to inhibit the upregulation of chemoresistance genes (Mdr1 and DHFR) during chemotherapy. Overall, the gene expression changes associated with BVDU treatment result in the decrease or prevention of chemoresistance. In addition, this agent has been shown to enhance the cytolytic activity of NK-92 natural killer cells towards a pancreatic cancer cell line in vitro.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/b2-1+/t7-,8+,9+/m0/s1
    2.1.3 InChI Key
    ODZBBRURCPAEIQ-PIXDULNESA-N
    2.1.4 Canonical SMILES
    C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)CO)O
    2.1.5 Isomeric SMILES
    C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)CO)O
    2.2 Other Identifiers
    2.2.1 UNII
    2M3055079H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (e)-5-(2-bromovinyl)-2'-deoxyuridine

    2. (z)-5-(2-bromovinyl)-2'-deoxyuridine

    3. 5-(2-bromoethenyl)-2'-deoxyuridine

    4. 5-(2-bromovinyl)-2'-deoxyuridine

    5. 5-bvdu

    6. Brivudin

    7. E-5-(2-bromovinyl)-durd

    8. Z-5-(2-bromovinyl)-durd

    9. Zostex

    2.3.2 Depositor-Supplied Synonyms

    1. 69304-47-8

    2. Bvdu

    3. (e)-5-(2-bromovinyl)-2'-deoxyuridine

    4. Brivudin

    5. Helpin

    6. Zostex

    7. Bromovinyldeoxyuridine

    8. Brivudine [inn]

    9. 5-bromovinyldeoxyuridine

    10. (e)-5-(2-bromovinyl)-deoxyuridine

    11. Rp101

    12. Rp-101

    13. Uridine, 5-[(1e)-2-bromoethenyl]-2'-deoxy-

    14. Uridine, 5-(2-bromovinyl)-2'-deoxy-, (e)-

    15. Brivudine (inn)

    16. Nsc-633770

    17. Ncgc00093656-01

    18. 2m3055079h

    19. 5-((e)-2-bromovinyl)-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

    20. Brivudinum

    21. Brivudina

    22. Brivudinum [inn-latin]

    23. Brivudina [inn-spanish]

    24. Mfcd00058585

    25. 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

    26. Bvd

    27. Ccris 2831

    28. 5-(2-bromovinyl)-2'-deoxyuridine

    29. Nsc 633770

    30. Trans-5-(2-bromovinyl)-2'-deoxyuridine

    31. Bridic

    32. Brivox

    33. Zerpex

    34. Brvdurd

    35. Nsc633770

    36. Unii-2m3055079h

    37. Uridine, 5-(2-bromoethenyl)-2'-deoxy-, (e)-

    38. Bv-durd

    39. Zostex (tn)

    40. (e)-5-(2-bromovinyl)-2-deoxyuridine

    41. Brivudine [mi]

    42. Brivudine [mart.]

    43. Brivudine [who-dd]

    44. Dsstox_cid_25755

    45. Dsstox_rid_81098

    46. Dsstox_gsid_45755

    47. Lopac0_000175

    48. Schembl99350

    49. Chembl31634

    50. Schembl141408

    51. (e)-5-(2-bromovinyl)-durd

    52. Dtxsid0045755

    53. Zinc3653378

    54. Tox21_111213

    55. Bdbm50366681

    56. S5009

    57. Ua-618

    58. Zb0745

    59. E-5-(2-bromovinyl)-2'-deoxyuridine

    60. Akos015833980

    61. Ccg-204270

    62. Cs-6292

    63. Db03312

    64. Lp00175

    65. Sdccgsbi-0050163.p002

    66. Ncgc00093656-02

    67. 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

    68. 5-[(e)-2-bromovinyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

    69. As-35234

    70. Hy-13578

    71. 5-[(e)-2-bromoethenyl]-2'-deoxyuridine

    72. Cas-69304-47-8

    73. A-176

    74. B3404

    75. Eu-0100175

    76. B 9647

    77. D07249

    78. 5-((e)-2-bromovinyl)-2'-deoxyuridine

    79. Q904107

    80. Sr-01000075726

    81. J-700153

    82. Sr-01000075726-1

    83. Bromovinyldeoxyuridine; 5-[(e)-2-bromoethenyl]-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 333.13 g/mol
    Molecular Formula C11H13BrN2O5
    XLogP3-0.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass332.00078 g/mol
    Monoisotopic Mass332.00078 g/mol
    Topological Polar Surface Area99.1 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity450
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

    4.2 ATC Code

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors

    J05AB15 - Brivudine