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Also known as: Cytarabin, 4-amino-1-pentofuranosylpyrimidin-2(1h)-one, .beta.-arabinosylcytosine, .beta.-cytosine arabinoside, .beta.-d-arabinosylcytosine, Cytosine-.beta.-arabinoside

Molecular Formula

C₉H₁₃N₃O₅

Molecular Weight

243.22 g/mol

InChI Key

UHDGCWIWMRVCDJ-UHFFFAOYSA-N

1-Beta-D-Arabinofuranosylcytosine Hydrochloride

A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)

1 2D Structure

1-Beta-D-Arabinofuranosylcytosine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

2.1.2 InChI

InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)

2.1.3 InChI Key

UHDGCWIWMRVCDJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Ara C

2. Ara-c

3. Arabinofuranosylcytosine

4. Arabinoside, Cytosine

5. Arabinosylcytosine

6. Aracytidine

7. Aracytine

8. Beta Ara C

9. Beta-ara C

10. Cytarabine

11. Cytarabine Hydrochloride

12. Cytonal

13. Cytosar U

14. Cytosar-u

15. Cytosine Arabinoside

2.2.2 Depositor-Supplied Synonyms

1. Cytarabin

2. 4-amino-1-pentofuranosylpyrimidin-2(1h)-one

3. .beta.-arabinosylcytosine

4. .beta.-cytosine Arabinoside

5. .beta.-d-arabinosylcytosine

6. Cytosine-.beta.-arabinoside

7. Arabinofuranosylcytosine

8. Aracytidine

9. Cytarabinoside

10. Spongocytidine

11. 1.beta.-d-arabinosylcytosine

12. Alexan

13. Mls003389283

14. Cytosine, .beta.-d-arabinoside

15. 1.beta.-arabinofuranasylcytosine

16. Arabinosylcytosine

17. Cytosine Arabinose

18. Nci-c04728

19. 1.beta.-d-arabinofuranosylcytosine

20. 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

21. Cytosine, 1-.beta.-d-arabinosyl-

22. Cytosine-.beta.-d-arabinofuranoside

23. 1-.beta.-d-arabinofaranosylcytosine

24. Cylocide

25. Nsc 63878

26. Cytosine, 1-.beta.-d-arabinofuranosyl-

27. 1-arabinofuranosylcytosine

28. 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1h)-one

29. Cytarabina

30. Arabitin

31. Arafcyt

32. Erpalfa

33. 688007-26-3

34. Iretin

35. 1-.beta.-d-arabinofuranosyl-4-amino-2(1h)pyrimidinone

36. Cytosine-beta-d-arabinofuranoside

37. Cytosine Beta-d-riboside;cytosine-1-beta-d-ribofuranoside

38. Cytosine Beta-d-arabinofuranoside;cytosine Arabinoside;ara-c

39. Mls002702869

40. 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one

41. Cytosine Beta-d-arabinofuranoside Hydrochloride;cytosine Arabinoside Hydrochloride;ara-c Hydrochloride

42. Smr001549941

43. 1.beta.-ribofuranosylcytosine

44. 1.beta.-d-ribofuranosylcytosine

45. 4-amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine

46. 1-.beta.-d-arabinofuranosylcytosine

47. U 19920

48. Mfcd00006545

49. Mfcd00066487

50. Nsc287459

51. .beta.-d-ribofuranoside, Cytosine-1

52. Cytarabine, Cytarabine (cytosine 1-b-d-arabinofuranoside), Cytidine

53. Cytosine, 1-.beta.-d-ribofuranosyl-

54. Ac-1075

55. Nsc 287459

56. Ac 1075

57. Chembl78

58. 4-amino-1.beta.-d-ribofuranosyl-2(1h)-pyrimidinone

59. Chemdiv1_027335

60. Molmap_000003

61. 2(1h)-pyrimidinone, 4-amino-1-.beta.-d-ribofuranosyl-

62. Oprea1_593929

63. Oprea1_858801

64. Schembl149563

65. Cytosine .beta.-d-arabinoside

66. 1-(b-d-xylofuranosyl)cytosine

67. Hms664k11

68. Dtxsid80859078

69. 1-.beta.-arabinofuranosylcytosine

70. 1-.beta.-d-ribofuranosylcytosine

71. Hms3371g12

72. Hms3393k19

73. Hms3428o03

74. Hms3655p13

75. Albb-021997

76. Chx-3311

77. Nsc20258

78. Bbl028243

79. Nsc249004

80. Stk391124

81. Akos001590380

82. Akos017259253

83. Cytosine-1-.beta.-d-arabinofuranoside

84. Nsc-249004

85. Smp2_000209

86. Ncgc00015258-02

87. Ncgc00015258-03

88. Ncgc00015258-04

89. Ncgc00015258-05

90. Ncgc00094638-01

91. Ncgc00094638-02

92. Ncgc00094638-03

93. Ncgc00094638-04

94. As-12090

95. Nci60_012951

96. Sy004943

97. Sy005417

98. Db-124991

99. U-19920 A

100. Ft-0624314

101. Ft-0624315

102. Ft-0774114

103. Wln: T6nvnj Dz A-bt5otj Cq Dq E1q

104. Ab01273973-01

105. L001298

106. Sr-01000597029

107. Sr-01000597029-1

108. 2(1h)-pyrimidinone, 4-amino-1.beta.-d-ribofuranosyl-

109. 4-amino-1-.beta.-d-arabinofuranosyl-2(1h)-pyrimidinon

110. 4-amino-1-.beta.-d-arabinofuranosyl-2(1h)-pyrimidinone

111. 2(1h)-pyrimidinone, 4-amino-1.beta.-d-arabinofuranosyl-

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₃N₃O₅
Molecular Weight	243.22 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	243.08552052 g/mol
Monoisotopic Mass	243.08552052 g/mol
Topological Polar Surface Area	129 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	383
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)

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.)

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