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    Chemistry

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    Also known as: Ast-3424, 2097713-69-2, Odafosfamide, Odafosfamide [inn], Schembl20870082, Schembl29392358
    Molecular Formula
    C21H25N4O6P
    Molecular Weight
    460.4  g/mol
    InChI Key
    NWGZZGNICQFUHV-HNNXBMFYSA-N
    FDA UNII
    C2T9S468D3
    (1S)-1-[3-[3-[(Dimethylamino)carbonyl]phenoxy]-4-nitrophenyl]ethyl P,P-bis(1-aziridinyl)phosphinate
    Odafosfamide is the S-isoform of odafosfamide, a small-molecule nitro-benzene, aldo-keto reductase 1C3 (AKR1C3)-activated prodrug of N,N'-bisethylenephosphoramidate, a DNA bis-alkylating agent, with potential antineoplastic activity. Upon intravenous administration, odafosfamide is converted to its active form by AKR1C3, which is upregulated in certain tumor cell types while not expressed in normal healthy cells. The active metabolite selectively binds to and alkylates DNA in AKR1C3-overexpressing tumor cells, resulting in DNA base pair mismatching, interstrand crosslinking and inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis. As the expression of AKR1C3 is restricted to tumors, Odafosfamide is selectively converted to its active metabolite in tumor cells only while its conversion in normal, healthy tissue is absent; this allows for an increased cytotoxic effect of the alkylating agent in tumor cells while decreasing its toxicity.
    1 2D Structure

    (1S)-1-[3-[3-[(Dimethylamino)carbonyl]phenoxy]-4-nitrophenyl]ethyl P,P-bis(1-aziridinyl)phosphinate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[5-[(1S)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
    2.1.2 InChI
    InChI=1S/C21H25N4O6P/c1-15(31-32(29,23-9-10-23)24-11-12-24)16-7-8-19(25(27)28)20(14-16)30-18-6-4-5-17(13-18)21(26)22(2)3/h4-8,13-15H,9-12H2,1-3H3/t15-/m0/s1
    2.1.3 InChI Key
    NWGZZGNICQFUHV-HNNXBMFYSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    C2T9S468D3
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Ast-3424

    2. 2097713-69-2

    3. Odafosfamide

    4. Odafosfamide [inn]

    5. Schembl20870082

    6. Schembl29392358

    7. C2t9s468d3

    8. Ex-a6317

    9. Obi-3424, (s)-

    10. Th-2870, (s)-

    11. (1s)-1-{3-[3-(dimethylcarbamoyl)phenoxy]-4-nitrophenyl}ethyl Bis(aziridin-1-yl)phosphinate

    12. 3-[5-[(1s)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-n,n-dimethylbenzamide

    13. Phosphinic Acid, P,p-bis(1-aziridinyl)-, (1s)-1-[3-[3-[(dimethylamino)carbonyl]phenoxy]-4-nitrophenyl]ethyl Ester

    2.4 Create Date
    2018-10-02
    3 Chemical and Physical Properties
    Molecular Weight 460.4 g/mol
    Molecular Formula C21H25N4O6P
    XLogP32.2
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count8
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area108
    Heavy Atom Count32
    Formal Charge0
    Complexity737
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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