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Chemistry

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Also known as: 9-nitrocamptothecin, 91421-42-0, 9-nitro-20(s)-camptothecin, Orathecin, 9-nc, Camptogen
Molecular Formula
C20H15N3O6
Molecular Weight
393.3  g/mol
InChI Key
VHXNKPBCCMUMSW-FQEVSTJZSA-N
FDA UNII
H19C446XXB

Rubitecan
Rubitecan is a semisynthetic agent related to camptothecin with potent antitumor and antiviral properties. Rubitecan binds to and inhibits the enzyme topoisomerase I and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells; this agent also prevents repair of reversible single-strand DNA breaks. (NCI04)
1 2D Structure

Rubitecan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
2.1.2 InChI
InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
2.1.3 InChI Key
VHXNKPBCCMUMSW-FQEVSTJZSA-N
2.1.4 Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
2.1.5 Isomeric SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
2.2 Other Identifiers
2.2.1 UNII
H19C446XXB
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9-nitro-20(s)-camptothecin

2. 9-nitrocamptothecin

3. 9-nitrocamptothecin, (s)-isomer

4. Rfs 2000

5. Rfs-2000

6. Rfs2000

2.3.2 Depositor-Supplied Synonyms

1. 9-nitrocamptothecin

2. 91421-42-0

3. 9-nitro-20(s)-camptothecin

4. Orathecin

5. 9-nc

6. Camptogen

7. Rfs 2000

8. Rfs-2000

9. (s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

10. 86639-62-5

11. Nitrocamptothecin

12. Rubitecan [usan]

13. Chebi:90225

14. Rfs2000

15. Rubitecan [usan:inn]

16. Unii-h19c446xxb

17. 9-nitro-(20s)-camptothecin

18. H19c446xxb

19. 9-nitro-20-(s)-camptothecin

20. Dtxsid7046752

21. Rfs 2000;9-nitrocamptothecin

22. (s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

23. 9nc

24. Ncgc00167969-01

25. (4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

26. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-10-nitro-, (4s)-

27. Rubitecanum

28. Inhaled Orathecin

29. C20h15n3o6

30. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-9-nitro-

31. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-9-nitro-

32. Rubitecan (inhaled)

33. 9-nitro Camptothecin

34. Rubitecan [inn]

35. Rubitecan [mi]

36. Rubitecan (usan/inn)

37. L9nc

38. D0i5xo

39. D0y1fo

40. Rubitecan [mart.]

41. Rubitecan [who-dd]

42. Schembl8640

43. 9-nitrocamptothecin (9-nc)

44. Ethyl-hydroxy-nitro-[?]dione

45. Chembl77305

46. Rubitecan (inhaled), Supergen

47. Camptothecin, 9-nitro-20(s)

48. Dtxcid5026752

49. Vhxnkpbccmumsw-fqevstjzsa-n

50. Bcp06207

51. Ex-a4326

52. Tox21_112597

53. Bdbm50248354

54. Mfcd06656294

55. S2288

56. Akos015895332

57. Akos025149224

58. C20-h15-n3-o6

59. Db06159

60. St-2617

61. Ncgc00167969-02

62. Ncgc00167969-03

63. Ac-13389

64. Ac-25083

65. Ac-33157

66. As-14856

67. Hy-13744

68. Cas-91421-42-0

69. Cs-0007769

70. N0822

71. D04031

72. A847954

73. Q510113

74. Aerosolized Liposomal 9 Nitro-20 (s) Camptothecin

75. Q-100889

76. Brd-k79821389-001-01-9

77. (19s)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

78. (s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3\',4\':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 393.3 g/mol
Molecular Formula C20H15N3O6
XLogP30.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area126
Heavy Atom Count29
Formal Charge0
Complexity861
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in pancreatic cancer, leukemia (unspecified), melanoma, ovarian cancer, and cancer/tumors (unspecified).


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Topoisomerase I Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)


5.2 Mechanism of Action

Rubitecan prevents DNA from unwinding during replication via DNA topoisomerase 1, therefore interfering with tumor growth.


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