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    Camsirubicin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Vi79rd8vnn, 236095-26-4, Gpx-150, Gpx150, Unii-vi79rd8vnn, Camsirubicin [inn]
    Molecular Formula
    C27H32N2O9
    Molecular Weight
    528.5  g/mol
    InChI Key
    GNCWGPLZJLZZPI-KUIJCEFOSA-N
    FDA UNII
    VI79RD8VNN
    Camsirubicin is a synthetic non-cardiotoxic analogue of the anthracycline antibiotic doxorubicin with potential antineoplastic activity. Camsirubicin intercalates DNA and impedes the activity of topoisomerase II, inducing single and double-stranded breaks in DNA; inhibiting DNA replication and/or repair, transcription, and protein synthesis; and activating tumor cell apoptosis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,10S)-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one
    2.1.2 InChI
    InChI=1S/C27H32N2O9/c1-11-23(31)14(28)8-17(37-11)38-16-10-27(35,6-7-30)9-13-19(16)26(34)20-21(25(13)33)24(32)12-4-3-5-15(36-2)18(12)22(20)29/h3-5,11,14,16-17,23,29-31,33-35H,6-10,28H2,1-2H3/t11-,14-,16-,17-,23+,27-/m0/s1
    2.1.3 InChI Key
    GNCWGPLZJLZZPI-KUIJCEFOSA-N
    2.1.4 Canonical SMILES
    CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(CCO)O)N)O
    2.1.5 Isomeric SMILES
    C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(CCO)O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    VI79RD8VNN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-imino-13-deoxydoxorubicin

    2. Gpx-150

    2.3.2 Depositor-Supplied Synonyms

    1. Vi79rd8vnn

    2. 236095-26-4

    3. Gpx-150

    4. Gpx150

    5. Unii-vi79rd8vnn

    6. Camsirubicin [inn]

    7. Camsirubicin [who-dd]

    8. 5-imino-13-deoxydoxorubicin

    9. (8r,10s)-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-5(8h)-naphthacenone

    10. (8r,10s)-10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxohexopyranosyl) Oxy)-6,8,11-trihydroxy-8-(2-hydroxyethyl)- 12-imino-1-methoxy-7,9,10,12-tetrahydrotetracen-5(8h)- One

    11. 5(8h)-naphthacenone, 10-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-, (8r,10s)-

    12. 5(8h)-naphthacenone, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,9,10,12-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyethyl)-12-imino-1-methoxy-, (8r,10s)-

    2.4 Create Date
    2019-01-15
    3 Chemical and Physical Properties
    Molecular Weight 528.5 g/mol
    Molecular Formula C27H32N2O9
    XLogP31.8
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count5
    Exact Mass528.21078060 g/mol
    Monoisotopic Mass528.21078060 g/mol
    Topological Polar Surface Area196 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity906
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1