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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 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 Formula	C₂₀H₁₅N₃O₆
Molecular Weight	393.3 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	1
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	126
Heavy Atom Count	29
Formal Charge	0
Complexity	861
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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