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    7 Ethyl 10 hydroxycamptothecin

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    2D Structure
    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

    2D Structure

    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 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.