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CAS 10212-25-6
PharmaCompass
  • Chemistry
CAS 10212-25-6
Also known as: Cyclocytidine hydrochloride, 10212-25-6, Cyclocytidine, Octd hydrochloride, 2,2'-o-cyclocytidine hydrochloride, Ancitabin hydrochlorid
Molecular Formula
C9H12ClN3O4
Molecular Weight
261.662  g/mol
InChI Key
KZOWNALBTMILAP-JBMRGDGGSA-N
FDA UNII
3T6920M469

Congener of CYTARABINE that is metabolized to cytarabine and thereby maintains a more constant antineoplastic action.
1 2D Structure

CAS 10212-25-6

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[1,2][1,3]oxazolo[3,4-a]pyrimidin-3-ol;hydrochloride
2.1.2 InChI
InChI=1S/C9H11N3O4.ClH/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8;/h1-2,4,6-8,10,13-14H,3H2;1H/t4-,6-,7+,8-;/m1./s1
2.1.3 InChI Key
KZOWNALBTMILAP-JBMRGDGGSA-N
2.1.4 Canonical SMILES
C1=CN2C3C(C(C(O3)CO)O)OC2=NC1=N.Cl
2.1.5 Isomeric SMILES
C1=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)OC2=NC1=N.Cl
2.2 Other Identifiers
2.2.1 UNII
3T6920M469
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Cyclocytidine Hydrochloride

2. 10212-25-6

3. Cyclocytidine

4. Octd Hydrochloride

5. 2,2'-o-cyclocytidine Hydrochloride

6. Ancitabin Hydrochlorid

7. Cyclo-cmp Hydrochloride

8. (-)-cyclocytidine Hydrochloride

9. Ancitabine Hcl

10. 2,2'-cyclocytidine Hydrochloride

11. Ancitabine (hydrochloride)

12. Cyclocytidine Hcl

13. 2,2'-anhydrocytarabine Hydrochloride

14. 2,2'-anhydroaracytidine Hydrochloride

15. 2,2'-anhydro-1-beta-d-arabinofuranosylcytosine Hydrochloride

16. 2,2'-anhydroarabinosylcytosine Hydrochloride

17. Unii-3t6920m469

18. Einecs 233-515-6

19. 2,2'-cyclocytidine, Monohydrochloride

20. Nsc 145668

21. Nsc-145668

22. O-2,2'-cyclocytidine Monohydrochloride

23. C9h11n3o4.hcl

24. Ancitabine Hydrochloride [jan]

25. Chebi:74843

26. 2,2'-anhydrocytidine Hydrochloride

27. Mfcd00012636

28. 2,2'-anhydro-1beta-d-arabinofuranosylcytosine Hydrochloride

29. Ak163009

30. 1beta-d-arabinofuranosylcytosine, 2,2'-anhydro-, Hydrochloride

31. Cyclo-c

32. 1-beta-d-arabinofuranosylcytosine, 2,2'-anhydro-, Hydrochloride

33. Cytosine, 1-beta-d-arabinofuranosyl-2,2'-anhydro-, Hydrochloride

34. Cytosine, 1beta-d-arabinofuranosyl-2,2'-anhydro-, Hydrochloride

35. Ancitabine Hydrochloride (jan)

36. Mls001173324

37. Ancitabin Hcl

38. 6h-furo(2',3':4,5)oxazolo(3,2-a)-pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, Monohydrochloride, Stereoisomer

39. Ancitabin Hydrochloride

40. Smr000538927

41. (2r,4r,5r,6s)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.0(2),?]dodeca-8,11-dien-5-ol Hydrochloride

42. Ac1q3evk

43. Ac1l18cc

44. Schembl98180

45. 2,2'-anhydro-(1-beta-d-arabinofuranosyl)cytosine Hydrochloride

46. Mls000766878

47. Mls001032024

48. Mls006011603

49. Chembl1255937

50. Kzownalbtmilap-jbmrgdggsa-n

51. Molport-005-938-291

52. Hy-n0093

53. 2,2'-cyclocytidine Monohydrochloride

54. S1973

55. 2, 2'-anhydro-cytidine Hydrochloride

56. Akos015896930

57. Ac-8697

58. An-7748

59. Cs-5313

60. Mcule-1704179569

61. As-12870

62. Bc215746

63. Ls-70869

64. Sc-09085

65. Ab0012527

66. Ax8006959

67. 3t6920m469

68. Bg00614372

69. Ft-0083570

70. St24046379

71. O2,2 Inverted Exclamation Marka-cyclocytidine

72. C13112

73. D01651

74. 698c143

75. J-700010

76. Ancitabine Hydrochloride (cyclocytidine Hydrochloride)

77. 2,2'-anhydro-(1-beta-d-arabinofuranosylcytosine) Hydrochloride

78. 2,2'-anhydro-1-(beta-d-arabinofuranosyl)cytosine Hydrochloride

79. Cyclocytidine Hydrochlorine; 2,2''-o-cyclocytidine Hydrochloride

80. 2,2 Inverted Exclamation Marka-anhydro-(1-

81. A-d-arabinofuranosyl)cytosine Hydrochloride

82. 2,2 Inverted Exclamation Marka-anhydro-1-

83. A-d-arabinofuranosylcytosine Hydrochloride

84. (2r,3r,3as,6e,9ar)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6h-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol Hydrochloride(1:1)

85. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6h-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol Hydrochloride

86. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6h-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ol Hydrochloride

87. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[1,2]oxazolo[3,4-a]pyrimidin-3-ol

88. 6h-furo(2',3':4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, Monohydrochloride, (2r-(2alpha,3beta,3abeta,9abeta))-

89. 6h-furo(2',3':4,5)oxazolo(3,2-a)pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, Monohydrochloride, (2r-(2alpha,3beta,3abeta,9abeta))- (9ci)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 261.662 g/mol
Molecular Formula C9H12ClN3O4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass261.052 g/mol
Monoisotopic Mass261.052 g/mol
Topological Polar Surface Area98.4 A^2
Heavy Atom Count17
Formal Charge0
Complexity394
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 Pharmacology

Ancitabine Hydrochloride is the hydrochloride salt of a cytarabine congener prodrug with antineoplastic activity. Upon administration, ancitabine is slowly hydrolyzed into cytarabine. Subsequently, cytarabine is converted to the triphosphate form within the cell and then competes with cytidine for incorporation into DNA. Because the arabinose sugar sterically hinders the rotation of the molecule within DNA, DNA replication ceases, specifically during the S phase of the cell cycle. Cytarabine agent also inhibits DNA polymerase, resulting in a decrease in DNA replication and repair. Compared to cytarabine, a more prolonged, consistent cytarabine-mediated therapeutic effect may be achieved with ancitabine because of the slow hydrolytic conversion of ancitabine to cytarabine.


4.2 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy.


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