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    Technical details about Aldoxorubicin, learn more about the structure, uses, toxicity, action, side effects and more

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    Aldoxorubicin

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    DIGITAL CONTENT

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    2D Structure
    1. Also known as: Inno-206, 1361644-26-9, Doxorubicin-emch, Doxo-emch, Aldoxorubicin [usan], N-[(e)-[1-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
    Molecular Formula
    C37H42N4O13
    Molecular Weight
    750.7  g/mol
    InChI Key
    OBMJQRLIQQTJLR-USGQOSEYSA-N
    FDA UNII
    C28MV4IM0B
    Aldoxorubicin is a 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity. Following intravenous administration, aldoxorubicin binds selectively to the cysteine-34 position of albumin via its maleimide moiety. Doxorubicin is released from the albumin carrier after cleavage of the acid-sensitive hydrazone linker within the acidic environment of tumors and, once located intracellularly, intercalates DNA, inhibits DNA synthesis, and induces apoptosis. Albumin tends to accumulate in solid tumors as a result of high metabolic turnover, rapid angiogenesis, hypervasculature, and impaired lymphatic drainage. Because of passive accumulation within tumors, this agent may improve the therapeutic effects of doxorubicin while minimizing systemic toxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(E)-[1-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
    2.1.2 InChI
    InChI=1S/C37H42N4O13/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43)/b39-23+/t17-,20-,22-,27-,32+,37-/m0/s1
    2.1.3 InChI Key
    OBMJQRLIQQTJLR-USGQOSEYSA-N
    2.1.4 Canonical SMILES
    CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)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=O)C(=CC=C5)OC)O)(/C(=N/NC(=O)CCCCCN6C(=O)C=CC6=O)/CO)O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    C28MV4IM0B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aldoxo

    2. Doxo-emch

    3. Inno-206

    2.3.2 Depositor-Supplied Synonyms

    1. Inno-206

    2. 1361644-26-9

    3. Doxorubicin-emch

    4. Doxo-emch

    5. Aldoxorubicin [usan]

    6. N-[(e)-[1-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide

    7. Aldoxorubicin (usan)

    8. 151038-96-9

    9. C28mv4im0b

    10. Aldoxorubicin [inn]

    11. Aldoxorubicin [who-dd]

    12. Chembl2107818

    13. Schembl15221892

    14. Dtxsid001098062

    15. Ex-a3971

    16. Aldoxorubicin;inno 206;inno206

    17. Nsc784722

    18. Zinc163337436

    19. Cs-1186

    20. Db06013

    21. Nsc-784722

    22. Hy-16261

    23. D10383

    24. (6-maleimidocaproyl)hydrazone Of Doxorubicin

    25. (8s)-1-methoxy-6,8alpha,11-trihydroxy-8-[1-[2-[6-(2,5-dioxo-3-pyrroline-1-yl)hexanoyl]hydrazono]-2-hydroxyethyl]-10alpha-(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyloxy)-7,8,9,10-tetrahydronaphthacene-5,12-dione

    26. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (1-((2s,4s)-4-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)-2-hydroxyethylidene)hydrazide

    27. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (1-(4-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)-2-hydroxyethylidene)hydrazide, (2s-cis)-

    28. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (2e)-2-(1-((2s,4s)-4-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)-2-hydroxyethylidene)hydrazide

    29. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (2e)-2-[1-[(2s,4s)-4-[(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]-2-hydroxyethylidene]hydrazide

    30. N'-((1e)-1-((2s,4s)-4-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxohexopyranosyl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl(-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)hexanohydrazide

    31. N'-((e)-1-((2s,4s)-4-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)hexanehydrazide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 750.7 g/mol
    Molecular Formula C37H42N4O13
    XLogP31.3
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count12
    Exact Mass750.27483741 g/mol
    Monoisotopic Mass750.27483741 g/mol
    Topological Polar Surface Area268 Ų
    Heavy Atom Count54
    Formal Charge0
    Complexity1510
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in solid tumors.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    INNO-206 is the (6-Maleimidocaproyl) hydrazone of doxorubicin. INNO-206 is a prodrug of doxorubicin that binds endogenous albumin after administration. The bound doxorubicin is released in the acidic environment of the tumor cell through cleavage of an acid sensitive linker. In preclinical models, INNO-206 was superior to doxorubicin with regard to antitumor efficacy and toxicity.

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