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Fludarabine
Also known as: 75607-67-9, Fludara, Fludarabine 5'-monophosphate, Oforta, Fludarabine monophosphate, 2-fluoro-ara amp
Molecular Formula
C10H13FN5O7P
Molecular Weight
365.21  g/mol
InChI Key
GIUYCYHIANZCFB-FJFJXFQQSA-N
FDA UNII
1X9VK9O1SC

1 2D Structure

Fludarabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
2.1.2 InChI
InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1
2.1.3 InChI Key
GIUYCYHIANZCFB-FJFJXFQQSA-N
2.1.4 Canonical SMILES
C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COP(=O)(O)O)O)O)F)N
2.1.5 Isomeric SMILES
C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)F)N
2.2 Other Identifiers
2.2.1 UNII
1X9VK9O1SC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9 Beta-d-arabinofuranosyl-2-fluoroadenine Monophosphate

2. 9h-purin-6-amine, 2-fluoro-9-(5-o-phosphono-beta-d-arabinofuranosyl)-

3. Beneflur

4. F-ara-amp

5. Faraamp

6. Fludara

7. Fludarabine 5'-monophosphate

8. Fludarabine Monophosphate

9. Fluoro-ara-amp

10. Nsc 312887

11. Nsc-312887

2.3.2 Depositor-Supplied Synonyms

1. 75607-67-9

2. Fludara

3. Fludarabine 5'-monophosphate

4. Oforta

5. Fludarabine Monophosphate

6. 2-fluoro-ara Amp

7. 2-f-ara-amp

8. Fludarabine (phosphate)

9. Famp

10. Nsc-312887

11. 2-fluoro-9-(5-o-phosphono-beta-d-arabinofuranosyl)-9h-purin-6-amine

12. ((2r,3s,4s,5r)-5-(6-amino-2-fluoro-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl Dihydrogen Phosphate

13. Chebi:63599

14. 2-fluoroadenine Arabinoside 5'-monophosphate

15. 1x9vk9o1sc

16. 9-beta-arabinofuranosyl-2-fluoroadenine-5'-phosphate

17. 9-beta-d-arabinofuranosyl-2-fluoroadenine 5'-monophosphate

18. 75607-67-9 (phosphate)

19. 9-beta-d-arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen Phosphate)

20. Fludarabine Phosphate (fludara)

21. {[(2r,3s,4s,5r)-5-(6-amino-2-fluoro-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic Acid

22. Nsc 312887

23. Nsc 328002

24. [(2r,3s,4s,5r)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

25. Nsc-328002

26. Smr002544683

27. F-ara-amp

28. Sr-05000001945

29. Unii-1x9vk9o1sc

30. Beneflur

31. Fludara Phosphate

32. Fludara (tn)

33. Fludarabine-phosphate

34. 2-fluoro-ara-amp

35. Mfcd00866418

36. Fludarabine Phosphate [usan:usp:ban]

37. Fludarabine Phosphate;

38. 2f-ara-amp

39. Schembl3511

40. Nsc 312887 Phosphate

41. Mls003915617

42. Mls004774150

43. 9-bata-d-arabinofuranosyl-2-fluoroadenine Phosphate

44. Fludarabine Phosphate(fludara)

45. 9-.beta.-d-arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen Phosphate)

46. Chembl1096882

47. Dtxsid2023060

48. Fludarabine Phosphate (jan/usp)

49. Sht-586

50. Fludarabine For System Suitability

51. Hms2094o11

52. Pharmakon1600-01505705

53. Fludarabine Phosphate [jan]

54. Ex-a2028

55. Hy-b0028

56. Nsc-118218h

57. Zinc3927870

58. Fludarabine Phosphate [usan]

59. Bdbm50248004

60. Fludarabine Phosphate [vandf]

61. Hg1010

62. Nsc759194

63. S1229

64. Fludarabine Phosphate [mart.]

65. 9h-purin-6-amine, 2-fluoro-9-(5-o-phosphono-beta-d-arabinofuranosyl)-

66. Akos024464516

67. Fludarabine Phosphate [usp-rs]

68. Fludarabine Phosphate [who-dd]

69. Bcp9000694

70. Ccg-213521

71. Cs-0861

72. F-ara-a (nsc 312887) Phosphate

73. Nsc-759194

74. Sri-5907-04

75. Sri-5907_05

76. Sri-5907_07

77. As-14202

78. Bcp0726000268

79. Fludarabine 5'-monophosphate [mi]

80. Fludarabine Phosphate [orange Book]

81. Sbi-0206893.p001

82. Fludarabine Phosphate [ep Monograph]

83. Fludarabine Phosphate [usp Monograph]

84. Sw218146-2

85. D01907

86. 607f679

87. A838460

88. Q185916

89. Sr-05000001945-1

90. Sr-05000001945-4

91. Z2235802254

92. 9-beta-d-arabinofuranosyl-2-fluoroadenine-5'-monophosphate

93. 9h-purin-6-amine, 2-fluoro-9-(5-o-phosphono-b-d-arabinofuranosyl)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 365.21 g/mol
Molecular Formula C10H13FN5O7P
XLogP3-3.1
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Exact Mass365.05366293 g/mol
Monoisotopic Mass365.05366293 g/mol
Topological Polar Surface Area186 Ų
Heavy Atom Count24
Formal Charge0
Complexity514
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFludarabine phosphate
Drug LabelFludarabine Phosphate Injection contains fludarabine phosphate, a fluorinated nucleotide analog of the antiviral agent vidarabine, 9- D-arabinofuranosyladenine (ara-A) that is relatively resistant to deamination by adenosine deaminase. Each mL cont...
Active IngredientFludarabine phosphate
Dosage FormInjectable
RouteInjection
Strength50mg/2ml (25mg/ml); 50mg/vial
Market StatusPrescription
CompanyHospira; Teva Pharms Usa; Sandoz; Actavis Elizabeth; Mustafa Nevzat Ilac; Fresenius Kabi Usa; Onco Therapies

2 of 2  
Drug NameFludarabine phosphate
Drug LabelFludarabine Phosphate Injection contains fludarabine phosphate, a fluorinated nucleotide analog of the antiviral agent vidarabine, 9- D-arabinofuranosyladenine (ara-A) that is relatively resistant to deamination by adenosine deaminase. Each mL cont...
Active IngredientFludarabine phosphate
Dosage FormInjectable
RouteInjection
Strength50mg/2ml (25mg/ml); 50mg/vial
Market StatusPrescription
CompanyHospira; Teva Pharms Usa; Sandoz; Actavis Elizabeth; Mustafa Nevzat Ilac; Fresenius Kabi Usa; Onco Therapies

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

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


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]
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