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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

SN38
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

SN38

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

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 392.4 g/mol
Molecular Formula C22H20N2O5
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass392.13722174 g/mol
Monoisotopic Mass392.13722174 g/mol
Topological Polar Surface Area100 Ų
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 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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