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    Annamycin

    ACTIVE PHARMA INGREDIENTS

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 92689-49-1, 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin, Snu299m83q, (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione, 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-, Unii-snu299m83q
    Molecular Formula
    C26H25IO11
    Molecular Weight
    640.4  g/mol
    InChI Key
    CIDNKDMVSINJCG-GKXONYSUSA-N
    FDA UNII
    SNU299M83Q
    Annamycin is a lipophilic, anthracycline antineoplastic antibiotic. Annamycin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and repair as well as inhibiting RNA and protein synthesis. This agent appears to not be a substrate for the p-glycoprotein associated multidrug-resistance (MDR) transporter; therefore, overcoming the resistance pattern seen with other anthracycline compounds.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
    2.1.2 InChI
    InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1
    2.1.3 InChI Key
    CIDNKDMVSINJCG-GKXONYSUSA-N
    2.1.4 Canonical SMILES
    CC1C(C(C(C(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O
    2.1.5 Isomeric SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    SNU299M83Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

    2.3.2 Depositor-Supplied Synonyms

    1. 92689-49-1

    2. 2'-iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin

    3. Snu299m83q

    4. (7s,9s)-7-(((2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione

    5. 5,12-naphthacenedione, 7-((2,6-dideoxy-2-iodo-alpha-l-mannopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7s-cis)-

    6. Unii-snu299m83q

    7. Ar-522

    8. (7s,9s)-7-[(2r,3r,4r,5r,6s)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione

    9. Schembl19368

    10. Dtxsid901027238

    11. Zinc3918134

    12. Db06420

    13. 689a491

    14. Q4767903

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 640.4 g/mol
    Molecular Formula C26H25IO11
    XLogP32.2
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count4
    Exact Mass640.04416 g/mol
    Monoisotopic Mass640.04416 g/mol
    Topological Polar Surface Area191 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity962
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    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 breast cancer and leukemia (unspecified).

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antibiotics, Antineoplastic

    Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

    5.2 Mechanism of Action

    Annamycin belongs to the anthracycline class of drugs, and has a pleiotropic mechanism of action where it targets topoisomerase II, causing strand breaks in DNA. Annamycin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.