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Doxifluridine

Doxifluridine

Synopsis, Chemistry

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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

Doxifluridine

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 Formula	C₉H₁₁FN₂O₅
Molecular Weight	246.19 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	246.06519962 g/mol
Monoisotopic Mass	246.06519962 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	399
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)