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    Lurtotecan

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 149882-10-0, Osi-211, Lurtotecan [inn], 4j1l80t08i, Gg-211, Nx-211
    Molecular Formula
    C28H30N4O6
    Molecular Weight
    518.6  g/mol
    InChI Key
    RVFGKBWWUQOIOU-NDEPHWFRSA-N
    FDA UNII
    4J1L80T08I
    Lurtotecan is a semisynthetic analogue of camptothecin with antineoplastic activity. Lurtotecan selectively stabilizes the topoisomerase I-DNA covalent complex and forms an enzyme-drug-DNA ternary complex. As a consequence of the formation of this complex, both the initial cleavage reaction and religation steps are inhibited and subsequent collision of the replication fork with the cleaved strand of DNA results in inhibition of DNA replication, double strand DNA breakage and triggering of apoptosis. Independent from DNA replication inhibition, lurtotecan also inhibits RNA synthesis, multi-ubiquitination and degradation of topoisomerase I and chromatin reorganization.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (18S)-18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.03,12.05,10.015,24.017,22]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione
    2.1.2 InChI
    InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1
    2.1.3 InChI Key
    RVFGKBWWUQOIOU-NDEPHWFRSA-N
    2.1.4 Canonical SMILES
    CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O
    2.1.5 Isomeric SMILES
    CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC6=C(C=C5N=C4C3=C2)OCCO6)CN7CCN(CC7)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    4J1L80T08I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(s)-camptothecin

    2. Gg-211

    3. Gg211

    4. Gi 147211

    5. Gi-147211

    6. Gi147211

    7. Gl 147211c

    8. Gl-147211c

    9. Gl147211c

    10. Nx 211

    11. Nx-211

    12. Nx211 Cpd

    13. Osi 211

    14. Osi-211

    15. Osi211

    2.3.2 Depositor-Supplied Synonyms

    1. 149882-10-0

    2. Osi-211

    3. Lurtotecan [inn]

    4. 4j1l80t08i

    5. Gg-211

    6. Nx-211

    7. Gi-147211

    8. Gg 211; Gi 147211; Lurtotecan; Nx 211; Osi 211

    9. Chembl341028

    10. (s)-8-ethyl-8-hydroxy-15-((4-methylpiperazin-1-yl)methyl)-11,14-dihydro-2h-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-9,12(3h,8h)-dione

    11. Osi 211

    12. Gg 211

    13. Nx 211

    14. Gi 147211

    15. Unii-4j1l80t08i

    16. Nx211 Cpd

    17. Lurtotecan [who-dd]

    18. Schembl19208

    19. Chembl305666

    20. Osi211

    21. Dtxsid30164422

    22. Gg211

    23. Gl147211c

    24. Gl 147211c

    25. Bdbm50036130

    26. Gw-211

    27. Zinc22010625

    28. Db12222

    29. Gl-147211c

    30. 11h-1,4-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione, 8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-, (8s)-

    31. Gi147211

    32. Hy-13670

    33. Cs-0007547

    34. A936765

    35. Q6704977

    36. D-myo-inositol2,4,5-trisphosphate,hexaammoniumsalt

    37. 7-(4-methylpiperazinomethylene)-10,11-ethylenedioxy-20(s)-camptothecin

    38. (18s)-18-ethyl-18-hydroxy-2-[(4-methylpiperazin-1-yl)methyl]-6,9,20-trioxa-13,24-diazahexacyclo[12.11.0.03,12.05,10.015,24.017,22]pentacosa-1,3,5(10),11,13,15,17(22)-heptaene-19,23-dione

    39. (8s)-8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-11h-p-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione

    40. (s)-8-ethyl-8-hydroxy-15-((4-methylpiperazin-1-yl)methyl)-2,3,11,14-tetrahydro-12h-[1,4]dioxino[2,3-g]pyrano[3',4':6,7]indolizino[1,2-b]quinoline-9,12(8h)-dione

    41. 11h-1,4-dioxino(2,3-g)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-9,12(8h,14h)-dione, 8-ethyl-2,3-dihydro-8-hydroxy-15-((4-methyl-1-piperazinyl)methyl)-, (s)

    42. 8-ethyl-8-hydroxy-15-(4-methylhexahydro-1-pyrazinylmethyl)-(8s)-2,3,8,9,12,14-hexahydro-11h-[1,4]dioxino[2,3-g]pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-9,12-dione With Trifluoroaceticacid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 518.6 g/mol
    Molecular Formula C28H30N4O6
    XLogP30.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count3
    Exact Mass518.21653469 g/mol
    Monoisotopic Mass518.21653469 g/mol
    Topological Polar Surface Area105 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity1070
    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.)