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Overview of CAS 86639-52-3

Client Email Product
(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione, AldrichCPR
PharmaCompass
(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3
Also known as: 7-ethyl-10-hydroxycamptothecin, 86639-52-3, Sn-38, 7-ethyl-10-hydroxy-camptothecin, Sn 38, 10-hydroxy-7-ethylcamptothecin
Molecular Formula
C22H20N2O5
Molecular Weight
392.411  g/mol
InChI Key
FJHBVJOVLFPMQE-QFIPXVFZSA-N
FDA UNII
0H43101T0J

7-ethyl-10-hydroxycamptothecin (SN 38) is a liposomal formulation of the active metabolite of Irinotecan [DB00762], a chemotherapeutic pro-drug approved for the treatment of advanced colorectal cancer. SN 38 has been used in trials studying the treatment of Cancer, Advanced Solid Tumors, Small Cell Lung Cancer, Metastatic Colorectal Cancer, and Triple Negative Breast Cancer, among others.
1 2D Structure

(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 InChI Key
FJHBVJOVLFPMQE-QFIPXVFZSA-N
2.1.3 Canonical SMILES
CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)C5(CC)O)O
2.1.4 Isomeric SMILES
CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)[C@@]5(CC)O)O
2.2 Other Identifiers
2.2.1 UNII
0H43101T0J
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 7-ethyl-10-hydroxycamptothecin

2. 86639-52-3

3. Sn-38

4. 7-ethyl-10-hydroxy-camptothecin

5. Sn 38

6. 10-hydroxy-7-ethylcamptothecin

7. 7-ethyl-10-hydroxycamptothecine

8. Le-sn38

9. Sn38

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

11. Unii-0h43101t0j

12. Captothecin, 7-ethyl-10-hydroxy-

13. Chebi:8988

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

15. 7-ethyl-10-hydroxy Camptothecin

16. Nsc673596

17. 0h43101t0j

18. (+)-7-ethyl-10-hydroxycamptothecin

19. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

20. 113015-38-6

21. C22h20n2o5

22. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

23. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione

24. 7-ethyl-10-hydroxy-20(s)-campthothecin

25. 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)

26. Nk 012

27. Nk-012

28. Avachem1025

29. Pubchem11040

30. Ac1l2xlk

31. D0b6yb

32. D0l5lg

33. Diethyl(dihydroxy)[?]dione

34. Schembl34018

35. Gtpl6925

36. Dtxsid4040399

37. 10-hydroxy-7-ethyl Camptothecin

38. 10-hydroxy-7-ethyl-camptothecin

39. Ks-00000nhr

40. 7-ethyl-10-hydroxy Campthotecin

41. Ex-a989

42. Fjhbvjovlfpmqe-qfipxvfzsa-n

43. Molport-002-317-317

44. Hms3652p12

45. 110714-48-2

46. Aob33769

47. Zinc4099013

48. 7-ethyl-10-hydroxy-20(s)-cpt

49. Bdbm50418088

50. Ce-042

51. Mfcd00871873

52. S4908

53. Akos015920433

54. Sn-38(nk-012)

55. Ac-1357

56. An-5834

57. Bcp9000200

58. Cs-1579

59. Db05482

60. Ls00055

61. Mcule-4181372030

62. Nsc-673596

63. Rl05364

64. Ncgc00167831-01

65. Aj-48031

66. Ak-36613

67. As-13533

68. Bc206169

69. Br-36613

70. Dr002275

71. Hy-13704

72. I605

73. Kb-46357

74. Nci60_026056

75. Pl072325

76. Sc-15667

77. 7-ethyl-10-hydroxy-20-(s)-camptothecine

78. Ab0013784

79. Ls-127394

80. Tl8005626

81. E0748

82. Ft-0630943

83. N2133

84. C11173

85. J90015

86. S-5119

87. 439e812

88. Q-100871

89. 7-ethyl-10-hydroxycamptothecin, >=98% (hplc), Powder

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

91. (19s)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0(2),(1)(1).0,.0(1),(2)]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

92. (19s)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0(2),(1)(1).0?,?.0(1)?,(2)?]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

93. (19s)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0(2),(1)(1).0?,?.0(1)?,(2)?]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

94. (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

95. (4s)-4,11-diethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione, Aldrichcpr

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

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

98. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4,7-diethyl-4,10-dihydroxy-

99. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (4s)-

100. 1h-pyrano[3',7]indolizino[1,2-b]quinoline- 3,14(4h,12h)-dione, 4,11-diethyl-4,9-dihydroxy-, (4s)-

101. Ehc

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

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 392.411 g/mol
Molecular Formula C22H20N2O5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass392.137 g/mol
Monoisotopic Mass392.137 g/mol
Topological Polar Surface Area100 A^2
Heavy Atom Count29
Formal Charge0
Complexity820
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 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 200–2000 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

Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.


Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.


Topoisomerase I Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE I.


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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