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    Narazaciclib

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    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 1357470-29-1, On123300, On-123300, Narazaciclib, Qj8ro3296g, Chembl3115681
    Molecular Formula
    C24H27N7O
    Molecular Weight
    429.5  g/mol
    InChI Key
    VADOZMZXXRBXNY-UHFFFAOYSA-N
    FDA UNII
    QJ8RO3296G
    Narazaciclib is an orally bioavailable inhibitor of NUAK family SNF1-like kinase 1 (AMPK-related protein kinase 5; ARK5), and the cyclin-dependent kinases 4 (CDK4) and 6 (CDK6), with potential antineoplastic activity. Upon oral administration,narazaciclib specifically binds to and inhibits ARK5, which interferes with the activation of ARK5-mediated signal transduction pathways and reduces cell proliferation in cancer cells that overexpress ARK5. In addition, ON 123300 inhibits CDK4 and 6 and prevents the phosphorylation of retinoblastoma (Rb) protein in early G1. Inhibition of Rb phosphorylation prevents CDK-mediated G1-S phase transition, which causes G1 phase cell cycle arrest, suppresses DNA synthesis and inhibits cancer cell growth. ARK5, a member of the AMP-activated protein kinase (AMPK) family, is associated with tumor growth and invasion. Overexpression of CDK4/6, which is seen in certain types of cancer, causes cell cycle deregulation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]-7-oxopyrido[2,3-d]pyrimidine-6-carbonitrile
    2.1.2 InChI
    InChI=1S/C24H27N7O/c1-29-10-12-30(13-11-29)20-8-6-19(7-9-20)27-24-26-16-18-14-17(15-25)23(32)31(22(18)28-24)21-4-2-3-5-21/h6-9,14,16,21H,2-5,10-13H2,1H3,(H,26,27,28)
    2.1.3 InChI Key
    VADOZMZXXRBXNY-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=C(C(=O)N(C4=N3)C5CCCC5)C#N
    2.2 Other Identifiers
    2.2.1 UNII
    QJ8RO3296G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. On123300

    2.3.2 Depositor-Supplied Synonyms

    1. 1357470-29-1

    2. On123300

    3. On-123300

    4. Narazaciclib

    5. Qj8ro3296g

    6. Chembl3115681

    7. Pyrido(2,3-d)pyrimidine-6-carbonitrile, 8-cyclopentyl-7,8-dihydro-2-((4-(4-methyl-1-piperazinyl)phenyl)amino)-7-oxo-

    8. 8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]-7-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

    9. Unii-qj8ro3296g

    10. On 123300

    11. Narazaciclib [inn]

    12. Schembl10050883

    13. Gtpl11879

    14. Bcp19186

    15. Ex-a1111

    16. Bdbm50447512

    17. Mfcd28411414

    18. Nsc802100

    19. S8161

    20. Akos030526450

    21. Zinc103269269

    22. Ccg-268995

    23. Cs-5570

    24. Nsc-802100

    25. Sb16989

    26. Compound 7x [pmid: 24417566]

    27. Ac-35541

    28. As-35286

    29. Hy-12624

    30. Db-100781

    31. A857300

    32. Q27287291

    33. 8-cyclopentyl-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile;on 123300

    34. 8-cyclopentyl-2-[4-(4-methyl-piperazine-1-yl)-phenylamino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

    2.4 Create Date
    2012-03-02
    3 Chemical and Physical Properties
    Molecular Weight 429.5 g/mol
    Molecular Formula C24H27N7O
    XLogP33.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass429.22770851 g/mol
    Monoisotopic Mass429.22770851 g/mol
    Topological Polar Surface Area88.4 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity754
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1