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    Doxifluridine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    ANALYTICAL

    PharmaCompass
    $ API Ref.Price (USD/KG) : 7,360Xls

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    2D Structure
    Also known as: 5'-deoxy-5-fluorouridine, 5-fluoro-5'-deoxyuridine, Furtulon, 3094-09-5, 5'-dfur, Flutron
    Molecular Formula
    C9H11FN2O5
    Molecular Weight
    246.19  g/mol
    InChI Key
    ZWAOHEXOSAUJHY-ZIYNGMLESA-N
    FDA UNII
    V1JK16Y2JP
    Doxifluridine is a fluoropyrimidine derivative and oral prodrug of the antineoplastic agent 5-fluorouracil (5-FU) with antitumor activity. Doxifluridine, designed to circumvent the rapid degradation of 5-FU by dihydropyrimidine dehydrogenase in the gut wall, is converted into 5-FU in the presence of pyrimidine nucleoside phosphorylase. 5-FU interferes with DNA synthesis and subsequent cell division by reducing normal thymidine production and interferes with RNA transcription by competing with uridine triphosphate for incorporation into the RNA strand.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
    2.1.3 InChI Key
    ZWAOHEXOSAUJHY-ZIYNGMLESA-N
    2.1.4 Canonical SMILES
    CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)O
    2.1.5 Isomeric SMILES
    C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(=O)NC2=O)F)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    V1JK16Y2JP
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5'-deoxy-5'-fluorouridine

    2. 5'-deoxy-5-fluorouridine

    3. 5'-dfur

    4. 5'-fluoro-5'-deoxyuridine

    5. Doxyfluridine

    6. Furtulon

    7. Ro 21-9738

    2.3.2 Depositor-Supplied Synonyms

    1. 5'-deoxy-5-fluorouridine

    2. 5-fluoro-5'-deoxyuridine

    3. Furtulon

    4. 3094-09-5

    5. 5'-dfur

    6. Flutron

    7. Uridine, 5'-deoxy-5-fluoro-

    8. Doxifluridina

    9. Doxifluridinum

    10. Fulturon

    11. Ro 219738

    12. Ro 21-9738

    13. Capecitabine Related Compound B

    14. 1-(beta-d-5-desoxyribofuranoxyl)-5-fluoruracil

    15. Chembl1130

    16. V1jk16y2jp

    17. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1h,3h)-dione

    18. Chebi:31521

    19. Nsc-758890

    20. Ncgc00093926-03

    21. Ro-219738

    22. Dsstox_cid_2967

    23. 5'fdur

    24. Dsstox_rid_76809

    25. Dsstox_gsid_22967

    26. Mfcd00866530

    27. 5'-doxifluridine

    28. 5'-dfurd

    29. Furtulon (tn)

    30. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-dione

    31. Smr000326811

    32. Cas-3094-09-5

    33. Uridine-5'-deoxy-5-fluoro-

    34. 5'dfurd

    35. Sr-01000075886

    36. Doxifluridine [inn:jan]

    37. 5-dfur

    38. Doxifluridinum [inn-latin]

    39. Doxifluridina [inn-spanish]

    40. Einecs 221-440-1

    41. 5-deoxy-5-fluorouridine

    42. Doxifluridine [mi]

    43. 5-fluoro-5`-deoxyuridine

    44. Unii-v1jk16y2jp

    45. Doxifluridine [inn]

    46. Doxifluridine [jan]

    47. Schembl8094

    48. Doxifluridine (jp17/inn)

    49. Lopac0_000537

    50. Mls001332579

    51. Mls001332580

    52. Mls002172440

    53. Mls002207077

    54. Doxifluridine [mart.]

    55. Doxifluridine [who-dd]

    56. Dtxsid2022967

    57. Hms2090c22

    58. Hms2231i05

    59. Hms3261l15

    60. Amc 0101

    61. Amy13408

    62. Hy-b0021

    63. Zinc1319177

    64. Tox21_111231

    65. Tox21_500537

    66. Bdbm50132295

    67. S2045

    68. Capecitabine Impurity B (usp)

    69. Akos015852921

    70. Akos015896821

    71. Tox21_111231_1

    72. Ccg-204627

    73. Cs-1270

    74. Db12947

    75. Ks-5065

    76. Lp00537

    77. Nsc 758890

    78. Sdccgsbi-0050520.p002

    79. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione

    80. Ncgc00093926-01

    81. Ncgc00093926-02

    82. Ncgc00093926-05

    83. Ncgc00093926-11

    84. Ncgc00261222-01

    85. Ro-21-9738

    86. Sri-11552-08

    87. Sri-11552_09

    88. 5''-deoxy-5-fluorouridine (5''-dfur)

    89. Eu-0100537

    90. D01309

    91. F 8791

    92. Capecitabine Related Compound B [usp-rs]

    93. 094f095

    94. Q1253473

    95. Sr-01000075886-1

    96. Sr-01000075886-5

    97. 5'-dfur (5'-deoxy-5-fluorouridine, Doxifluridine)

    98. Brd-k58262659-001-09-7

    99. Capecitabine Related Compound B [usp Impurity]

    100. 1-(.beta.-d-5-desoxyribofuranoxyl)-5-fluoruracil

    101. Capecitabine Impurity B, European Pharmacopoeia (ep) Reference Standard

    102. Capecitabine Related Compound B, United States Pharmacopeia (usp) Reference Standard

    103. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1h,3h)-dione

    104. 1-((2r,5r)-3,4-dihydroxy-5-methyl-tetrahydro-furan-2-yl)-5-fluoro-1h-pyrimidine-2,4-dione

    105. 1-((4s,2r,3r,5r)-3,4-dihydroxy-5-methyloxolan-2-yl)-5-fluoro-1,3-dihydropyrimidine-2,4-dione

    106. 1-(5-deoxy-beta-d-ribofuranosyl)-5-fluoropyrimidine-2,4(1h,3h)-dione (5'-deoxy-5-fluorouridine)

    107. Furtulon, Flutron, Doxyfluridine, Doxifluridina, Doxifluridinum 5'-doxifluridine, 5'dfurd, 5-fluoro-5'-deoxyuridine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 246.19 g/mol
    Molecular Formula C9H11FN2O5
    XLogP3-1.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count1
    Exact Mass246.06519962 g/mol
    Monoisotopic Mass246.06519962 g/mol
    Topological Polar Surface Area99.1 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity399
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antimetabolites, Antineoplastic

    Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

    Appetite Stimulants

    Agents that are used to stimulate appetite. These drugs are frequently used to treat anorexia associated with cancer and AIDS. (See all compounds classified as Appetite Stimulants.)

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)