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Chemistry

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Also known as: Cyclocytidine hydrochloride, 10212-25-6, Cyclocytidine, 2,2'-o-cyclocytidine hydrochloride, Cyclo-cmp hydrochloride, Cyclocytidine hcl

Molecular Formula

C₉H₁₂ClN₃O₄

Molecular Weight

261.66 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

Cyclocytidine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,4R,5R,6S)-4-(hydroxymethyl)-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-5-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 MeSH Synonyms

1. Ancitabine

2. Anhydro-ara-c

3. Cyclo C

4. Cyclo-c

5. Cycloc

6. Cyclocytidine

7. Nsc 145,668

8. Nsc 145668

9. Nsc-145,668

10. Nsc-145668

11. Nsc145,668

12. Nsc145668

13. U 33,624a

14. U 33624a

15. U-33,624a

16. U-33624a

17. U33,624a

18. U33624a

2.3.2 Depositor-Supplied Synonyms

1. Cyclocytidine Hydrochloride

2. 10212-25-6

3. Cyclocytidine

4. 2,2'-o-cyclocytidine Hydrochloride

5. Cyclo-cmp Hydrochloride

6. Cyclocytidine Hcl

7. Octd Hydrochloride

8. Ancitabin Hydrochlorid

9. Ancitabine Hcl

10. Ancitabine (hydrochloride)

11. 2,2'-anhydrocytarabine Hydrochloride

12. 2,2'-anhydroaracytidine Hydrochloride

13. Nsc-145668

14. 2,2'-anhydro-1-beta-d-arabinofuranosylcytosine Hydrochloride

15. Ancitabine Hydrochloride [jan]

16. 2,2'-anhydroarabinosylcytosine Hydrochloride

17. (-)-cyclocytidine Hydrochloride

18. Cyclo-c

19. 2,2'-cyclocytidine Hydrochloride

20. Chebi:74843

21. 2,2'-anhydrocytidine Hydrochloride

22. 3t6920m469

23. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-3,3a,6,9a-tetrahydro-2h-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-ol Hydrochloride

24. Ancitabine Hydrochloride (jan)

25. Mls001173324

26. Ancitabin Hcl

27. Ancitabin Hydrochloride

28. Smr000538927

29. Einecs 233-515-6

30. 2,2'-cyclocytidine, Monohydrochloride

31. Nsc 145668

32. O-2,2'-cyclocytidine Monohydrochloride

33. Unii-3t6920m469

34. Mfcd00012636

35. 2,2'-anhydro-1beta-d-arabinofuranosylcytosine Hydrochloride

36. 1beta-d-arabinofuranosylcytosine, 2,2'-anhydro-, Hydrochloride

37. 1-beta-d-arabinofuranosylcytosine, 2,2'-anhydro-, Hydrochloride

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

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

40. Schembl98180

41. Mls000766878

42. Mls001032024

43. Mls006011603

44. Nsc 145668 Hcl

45. Chembl1255937

46. Hy-n0093

47. 2,2'-cyclocytidine Monohydrochloride

48. Ancitabine Hydrochloride [mi]

49. S1973

50. Akos015896930

51. Ac-8697

52. Ccg-267066

53. Cs-5313

54. Ancitabine Hydrochloride [mart.]

55. Ancitabine Hydrochloride [who-dd]

56. 6h-furo(2',3':4,5)oxazolo(3,2-a)-pyrimidine-2-methanol, 2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-, Monohydrochloride, Stereoisomer

57. 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))-

58. As-12870

59. Tl8000113

60. D01651

61. 698c143

62. J-700010

63. Q27144957

64. 2,2'-anhydro-(1-beta-d-arabinofuranosylcytosine) Hydrochloride

65. 2,2'-anhydro-1-(beta-d-arabinofuranosyl)cytosine Hydrochloride

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

67. (2r,3r,3as,9ar)-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6h-furo(2',3';4,5)oxazolo(3,2-a)pyrimidine-2-methanol, Hydrochloride

68. (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

69. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydrofuro[1,2]oxazolo[3,4-a]pyrimidin-3-ol

70. (2r,3r,3as,9ar)-2-(hydroxymethyl)-6-imino-3,3a,6,9a-tetrahydro-2h-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-olhydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₂ClN₃O₄
Molecular Weight	261.66 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	261.0516336 g/mol
Monoisotopic Mass	261.0516336 g/mol
Topological Polar Surface Area	98.4 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	394
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	2

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.)

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