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Chemistry

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Also known as: 86639-52-3, Sn-38, Sn 38, Sn 38 lactone, (s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 10-hydroxy-7-ethylcamptothecin

Molecular Formula

C₂₂H₂₀N₂O₅

Molecular Weight

392.4 g/mol

InChI Key

FJHBVJOVLFPMQE-QFIPXVFZSA-N

FDA UNII

0H43101T0J

A semisynthetic camptothecin derivative that inhibits DNA TOPOISOMERASE I to prevent nucleic acid synthesis during S PHASE. It is used as an antineoplastic agent for the treatment of COLORECTAL NEOPLASMS and PANCREATIC NEOPLASMS.

1 2D Structure

7-Ethyl-10-Hydroxycamptothecin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(19S)-10,19-diethyl-7,19-dihydroxy-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/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1

2.1.3 InChI Key

FJHBVJOVLFPMQE-QFIPXVFZSA-N

2.1.4 Canonical SMILES

CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)O

2.1.5 Isomeric SMILES

CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)O

2.2 Other Identifiers

2.2.1 UNII

0H43101T0J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7 Ethyl 10 Hydroxycamptothecin

2. Camptosar

3. Camptothecin 11

4. Camptothecin-11

5. Cpt 11

6. Cpt-11

7. Cpt11

8. Irinotecan

9. Irinotecan Hydrochloride

10. Irrinotecan

11. Nk012 Compound

12. Sn 38

13. Sn 38 11

14. Sn-38

15. Sn-38-11

16. Sn3811

2.3.2 Depositor-Supplied Synonyms

1. 86639-52-3

2. Sn-38

3. Sn 38

4. Sn 38 Lactone

5. (s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

6. 10-hydroxy-7-ethylcamptothecin

7. Nk 012

8. Sn38

9. 7-ethyl-10-hydroxy-20(s)-camptothecin

10. Nk012

11. Nk-012

12. Irinotecan Related Compound B

13. Chebi:8988

14. 113015-38-6

15. It-141

16. Nsc673596

17. 0h43101t0j

18. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

19. (+)-7-ethyl-10-hydroxycamptothecin

20. (19s)-10,19-diethyl-7,19-dihydroxy-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

21. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

22. 7-ethyl-10-hydroxy-20(s)-campthothecin

23. Le-sn38

24. Captothecin, 7-ethyl-10-hydroxy-

25. Mfcd00871873

26. Unii-0h43101t0j

27. 110714-48-2

28. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (4s)-

29. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (4s)-

30. Avachem1025

31. Diethyl(dihydroxy)[?]dione

32. Sn 38- Bio-x

33. Schembl34018

34. Gtpl6925

35. Sn 38 [who-dd]

36. Dtxsid4040399

37. 10-hydroxy-7-ethyl Camptothecin

38. 10-hydroxy-7-ethyl-camptothecin

39. 7-ethyl-10-hydroxy Campthotecin

40. Ex-a989

41. Hms3413b12

42. Hms3652p12

43. Hms3677b12

44. Bcp01386

45. Zinc4099013

46. 7-ethyl-10-hydroxy-20(s)-cpt

47. Bdbm50418088

48. S4908

49. Akos015920433

50. Sn-38(nk-012)

51. Ac-1357

52. Bcp9000200

53. Ccg-264764

54. Cs-1579

55. Db05482

56. Nsc-673596

57. Ncgc00167831-01

58. Ncgc00167831-05

59. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione

60. As-13533

61. Be164132

62. Bp-24513

63. Hy-13704

64. Nci60_026056

65. Camptothecin, 7-ethyl-10-hydroxy-

66. E0748

67. N2133

68. Sw219948-1

69. S-(+)-7-ethyl-10-hydroxycampothecin

70. Irinotecan Related Compound B [usp-rs]

71. 439e812

72. A857464

73. Q-100871

74. Q1750127

75. 7-ethyl-10-hydroxycamptothecin, >=98% (hplc), Powder

76. Irinotecan Related Compound B, United States Pharmacopeia (usp) Reference Standard

77. (19s)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

78. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione, Aldrichcpr

79. (4s)-4,9-dihydroxy-4,11-diethyl-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione;sn-38

80. (s)-4,11-diethyl-4,9-di-oh-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

81. 1h-pyrano[3',7]indolizino[1,2-b]quinoline- 3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (4s)-

82. 7-ethyl-10-hydroxycamptothecin ((s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione)

83. H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (s)-

84. Rs4

2.3.3 Other Synonyms

1. Sn-38 Glucuronide

2. Sn-38g

3. Sn38 Glucuronide

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₀N₂O₅
Molecular Weight	392.4 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	392.13722174 g/mol
Monoisotopic Mass	392.13722174 g/mol
Topological Polar Surface Area	100 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	820
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 colorectal cancer.

5 Pharmacology and Biochemistry

5.1 Pharmacology

SN-38 (7-ethyl-10-hydroxycamptothecin) is the active metabolite of Irinotecan (CPT-11). Irinotecan is a topoisomerase I inhibitor commercially available as Camptosar. SN-38 has been found to be 2002000 times more cytotoxic than CPT-11, but has not been used as an anticancer drug due to its poor solubility in pharmaceutically acceptable solvents and low affinity to lipid membranes. SN-38 also undergoes a reversible conversion to an inactive open lactone ring structure at physiological pH. LE-SN-38 is a novel lipsome based formulation containing liposomes of uniform size distribution (<200 nm). Drug entrapment efficiency of the formulation is>95%.

5.2 MeSH Pharmacological Classification

Topoisomerase I Inhibitors

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

5.3 Mechanism of Action

The entrapment of SN-38 in lipsomes results in a more stable and more soluble form of the drug. This allows for increased affinity of SN-38 to lipid membranes and improved delivery of the drug to tumor sites. SN-38 is a highly effective cytotoxic topoisomerase I inhibitor.

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