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    Chemistry

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    Also known as: Kb-0742, 2416873-83-9, Chembl5199065, Kb0742, Istisociclib (usan), Istisociclib [usan]
    Molecular Formula
    C16H25N5
    Molecular Weight
    287.40  g/mol
    InChI Key
    VYKCLMALANGCDF-STQMWFEESA-N
    FDA UNII
    F7J6KSY5I8
    Istisociclib
    Istisociclib is an orally bioavailable, selective inhibitor of the serine/threonine cyclin-dependent kinase 9 (CDK9), the catalytic subunit of the RNA polymerase II (RNA Pol II) elongation factor positive transcription elongation factor b (PTEF-b; PTEFb), with potential antineoplastic activity. Upon oral administration, istisociclib targets, binds to and blocks the phosphorylation and kinase activity of CDK9, thereby preventing PTEFb-mediated activation of RNA Pol II, leading to the inhibition of gene transcription of various anti-apoptotic proteins and oncogenic transcription factors including MYC and androgen receptor (AR). This induces cell cycle arrest and apoptosis and prevents tumor cell proliferation. CDK9 regulates elongation of transcription through phosphorylation of RNA Pol II at serine 2 (p-Ser2-RNAPII), and is an important cofactor for various oncogenic transcription factors. It is upregulated in various tumor cell types and plays a key role in the regulation of Pol II-mediated transcription of anti-apoptotic proteins. Tumor cells are dependent on anti-apoptotic proteins for their survival.
    1 2D Structure

    Istisociclib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,3S)-3-N-(5-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine
    2.1.2 InChI
    InChI=1S/C16H25N5/c1-3-11(4-2)14-10-16(19-13-6-5-12(17)9-13)21-15(20-14)7-8-18-21/h7-8,10-13,19H,3-6,9,17H2,1-2H3/t12-,13-/m0/s1
    2.1.3 InChI Key
    VYKCLMALANGCDF-STQMWFEESA-N
    2.2 Other Identifiers
    2.2.1 UNII
    F7J6KSY5I8
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Kb-0742

    2. 2416873-83-9

    3. Chembl5199065

    4. Kb0742

    5. Istisociclib (usan)

    6. Istisociclib [usan]

    7. (1s,3s)-3-n-(5-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine

    8. (1s,3s)-n1-(5-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine

    9. Istisociclib [inn]

    10. F7j6ksy5i8

    11. Kb0742 2hcl

    12. Orb1089900

    13. Kb-0742 Hcl?

    14. Schembl21877722

    15. Gtpl13068

    16. Ex-a6433

    17. Bdbm50593922

    18. Nsc834161

    19. Nsc-834161

    20. Compound 28 [pmid: 37967851]

    21. Ub-18422

    22. Hy-137478

    23. Kb-130742

    24. Cs-0139025

    25. Kb-00130742

    26. D12868

    27. (1s,3s)-3-amino-1-[5-(1-ethylpropyl)-1,4,7a-triazainden-7-ylamino]cyclopentane

    28. (1s,3s)-n1-[5-(1-ethylpropyl)pyrazolo[1,5-a]pyrimidin-7-yl]-1,3-cyclopentanediamine

    29. 1,3-cyclopentanediamine, N1-[5-(1-ethylpropyl)pyrazolo[1,5-a]pyrimidin-7-yl]-, (1s,3s)-

    2.4 Create Date
    2020-06-27
    3 Chemical and Physical Properties
    Molecular Weight 287.40 g/mol
    Molecular Formula C16H25N5
    XLogP32.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area68.2
    Heavy Atom Count21
    Formal Charge0
    Complexity333
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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