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    Zotatifin

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 2098191-53-6, Eft226, Eft-226, Zotatifin [inn], Zotatifin [usan], 2ewn8z05cn
    Molecular Formula
    C28H29N3O5
    Molecular Weight
    487.5  g/mol
    InChI Key
    QYCXWOACFWMQFO-WZWZCULESA-N
    FDA UNII
    2EWN8Z05CN
    Zotatifin is a selective inhibitor of the eukaryotic translation initiation factor 4A (eIF4A), with potential antineoplastic activity. Upon administration of zotatifin, this agent targets and binds to elF4A, and promotes eIF4A binding to mRNA with specific polypurine motifs within their 5'-untranslated region (5'-UTR), leading to the formation of a stable sequence-specific ternary complex with eIF4A and mRNA (elF4A- zotatifin-mRNA). This results in the translational repression of key oncogenes and anti-apoptotic proteins involved in tumor cell proliferation, survival and metastasis, such as KRAS, Myc, myeloid cell leukemia-1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), cyclin-dependent kinase (CDK) 4 and 6, cyclin D, fibroblast growth factor receptor (FGFR) 1 and 2, human epidermal growth factor receptor 2 (HER2; ERBB2), and beta-catenin. The inhibition of the expression of these oncogenes leads to the inhibition of various oncogenic signal transduction pathways. This inhibits proliferation and induces apoptosis in tumor cells. eIF4A, a RNA helicase and the rate-limiting component of the eukaryotic translation initiation complex, catalyzes the ATP-dependent unwinding of RNA duplexes and facilitates 43S ribosome scanning within the 5'-UTR. elF4A is activated by various oncogenic signaling pathways, including RAS/mitogen-activated protein kinase (MAPK) and phosphatidylinositide 3-kinase (PI3K)/AKT pathways, and regulates the translation of oncogenes and tumor survival factors with complex secondary structures within the 5'-UTRs that are required for tumor cell proliferation, survival and metastasis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(2S,3R,4S,5S,6R)-4-[(dimethylamino)methyl]-2,3-dihydroxy-10,12-dimethoxy-5-phenyl-7-oxa-11-azatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-6-yl]benzonitrile
    2.1.2 InChI
    InChI=1S/C28H29N3O5/c1-31(2)16-20-23(18-8-6-5-7-9-18)28(19-12-10-17(15-29)11-13-19)27(33,25(20)32)24-21(36-28)14-22(34-3)30-26(24)35-4/h5-14,20,23,25,32-33H,16H2,1-4H3/t20-,23-,25-,27+,28+/m1/s1
    2.1.3 InChI Key
    QYCXWOACFWMQFO-WZWZCULESA-N
    2.1.4 Canonical SMILES
    CN(C)CC1C(C2(C(C1O)(C3=C(N=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)C#N)C5=CC=CC=C5
    2.1.5 Isomeric SMILES
    CN(C)C[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(N=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)C#N)C5=CC=CC=C5
    2.2 Other Identifiers
    2.2.1 UNII
    2EWN8Z05CN
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 2098191-53-6

    2. Eft226

    3. Eft-226

    4. Zotatifin [inn]

    5. Zotatifin [usan]

    6. 2ewn8z05cn

    7. 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-6,7,8,8a-tetrahydro-5ah-cyclopenta[4,5]furo[3,2-c]pyridin-5a-yl)benzonitrile

    8. 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-6,7,8,8a-tetrahydro-5ah-cyclopenta(4,5)furo(3,2-c)pyridin-5a-yl)benzonitrile

    9. Benzonitrile, 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-6,7,8,8a-tetrahydro-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-5ah-cyclopenta(4,5)furo(3,2-c)pyridin-5a-yl)-

    10. Zotafin

    11. Rel-zotatifin

    12. Zotatifin (usan/inn)

    13. Unii-2ewn8z05cn

    14. Zotatifin [who-dd]

    15. Chembl4303782

    16. Schembl18864788

    17. Dtxsid001022536

    18. Ex-a4623

    19. Bdbm50540861

    20. Nsc818001

    21. Nsc828584

    22. Who 10998

    23. Nsc-818001

    24. Nsc-828584

    25. Hy-112163

    26. Cs-0043584

    27. D11837

    28. A937238

    29. 4-[(2s,3r,4s,5s,6r)-4-[(dimethylamino)methyl]-2,3-dihydroxy-10,12-dimethoxy-5-phenyl-7-oxa-11-azatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-6-yl]benzonitrile

    2.4 Create Date
    2017-08-04
    3 Chemical and Physical Properties
    Molecular Weight 487.5 g/mol
    Molecular Formula C28H29N3O5
    XLogP32.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count6
    Exact Mass487.21072103 g/mol
    Monoisotopic Mass487.21072103 g/mol
    Topological Polar Surface Area108 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity819
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1