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Chemistry

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Also known as: 91421-43-1, Aminocamptothecin, 9-amino-camptothecin, 9-amino-cpt, 9-amino-20(s)-camptothecin, 9-amino-20-(s)-camptothecin
Molecular Formula
C20H17N3O4
Molecular Weight
363.4  g/mol
InChI Key
FUXVKZWTXQUGMW-FQEVSTJZSA-N
FDA UNII
5MB77ICE2Q

9-Aminocamptothecin
Aminocamptothecin is a water-insoluble camptothecin derivative. Aminocamptothecin binds to the nuclear enzyme topoisomerase I, thereby inhibiting repair of single-strand DNA breakages. Because the terminal lactone ring of aminocamptothecin required for the agent's antitumor activity spontaneously opens under physiological conditions to an inactive carboxy form, the drug must be administered over an extended period of time to achieve effective cytotoxicity. (NCI04)
1 2D Structure

9-Aminocamptothecin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
2.1.2 InChI
InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1
2.1.3 InChI Key
FUXVKZWTXQUGMW-FQEVSTJZSA-N
2.1.4 Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O
2.1.5 Isomeric SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O
2.2 Other Identifiers
2.2.1 UNII
5MB77ICE2Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9-amino-20(s)-camptothecin

2. 9-amino-20-camptothecin, (+-)-isomer

3. 9-amino-20-camptothecin, (r,s)-isomer

4. 9-amino-cpt

5. Nsc 603071

2.3.2 Depositor-Supplied Synonyms

1. 91421-43-1

2. Aminocamptothecin

3. 9-amino-camptothecin

4. 9-amino-cpt

5. 9-amino-20(s)-camptothecin

6. 9-amino-20-(s)-camptothecin

7. Nsc-603071

8. Nsc603071

9. 5mb77ice2q

10. Chembl274070

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

12. Chebi:80755

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

14. Camptothecin, 9-amino-

15. (19s)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

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

17. 10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

18. 10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

19. Mls002702905

20. Unii-5mb77ice2q

21. Nsc 603071

22. Idec-132

23. Nsc-629971

24. 9-aminocamptothecan

25. 9-amino Camptothecin

26. 9-nh2-camptothecin

27. 9-amino-2(s)-camptothecin

28. Schembl26578

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

30. Cid_72402

31. Mls000728575

32. 9-aminocamptothecin [mi]

33. Dtxsid10873202

34. Hms2220k11

35. Hms3339h11

36. Hms3749c03

37. 10-amino-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

38. Bcp09002

39. Ex-a4335

40. 9-amino-cpt (9-aminocamptothecin)

41. Bdbm50008936

42. Mfcd00909855

43. S2653

44. Zinc37866089

45. 9-aminocamptothecin [who-dd]

46. Akos015896595

47. Cs-7784

48. Db12515

49. Ncgc00247552-01

50. 1h-pyrano(3;,4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (s)-

51. Ac-33991

52. As-14292

53. Nci60_004578

54. Smr000445687

55. Hy-100309

56. F11420

57. 421a431

58. A843867

59. J-504140

60. Brd-k09291936-001-07-5

61. Q27149808

62. (s)-10-amino-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

63. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (4s)-

64. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione,4-ethyl-4-hydroxy-9-nitro-

65. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 10-amino-4-ethyl-4-hydroxy-, (s)-

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 363.4 g/mol
Molecular Formula C20H17N3O4
XLogP30.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass363.12190603 g/mol
Monoisotopic Mass363.12190603 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count27
Formal Charge0
Complexity775
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents

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


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