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    Chemistry

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    Also known as: 1255at22zj, Unii-1255at22zj, Vip152, Chembl4762845, Vip-152, Bay-1251152
    Molecular Formula
    C19H18F2N4O2S
    Molecular Weight
    404.4  g/mol
    InChI Key
    YZCUMZWULWOUMD-NDEPHWFRSA-N
    FDA UNII
    1255AT22ZJ
    Enitociclib
    Enitociclib is an inhibitor of 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 administration, enitociclib binds to and blocks the phosphorylation and kinase activity of CDK9, thereby preventing PTEFb-mediated activation of RNA Pol II and leading to the inhibition of gene transcription of various anti-apoptotic proteins. This may cause cell cycle arrest and induce apoptosis, which may lead to a reduction in tumor cell proliferation. The protein complex PTEF-b, a heterodimer consisting of CDK9 and a regulatory cyclin subunit of the T family, is over-activated in various tumor cell types; it 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

    Enitociclib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-[4-[(methylsulfonimidoyl)methyl]pyridin-2-yl]pyridin-2-amine
    2.1.2 InChI
    InChI=1S/C19H18F2N4O2S/c1-27-17-8-13(20)3-4-14(17)15-9-19(24-10-16(15)21)25-18-7-12(5-6-23-18)11-28(2,22)26/h3-10,22H,11H2,1-2H3,(H,23,24,25)/t28-/m0/s1
    2.1.3 InChI Key
    YZCUMZWULWOUMD-NDEPHWFRSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=CC(=C1)F)C2=CC(=NC=C2F)NC3=NC=CC(=C3)CS(=N)(=O)C
    2.1.5 Isomeric SMILES
    COC1=C(C=CC(=C1)F)C2=CC(=NC=C2F)NC3=NC=CC(=C3)C[S@@](=N)(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    1255AT22ZJ
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1255at22zj

    2. Unii-1255at22zj

    3. Vip152

    4. Chembl4762845

    5. Vip-152

    6. Bay-1251152

    7. 1610408-97-3

    8. 2-pyridinamine, 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-(4-(((s(s))-s-methylsulfonimidoyl)methyl)-2-pyridinyl)-

    9. 2-pyridinamine, 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-[4-[[[s(s)]-s-methylsulfonimidoyl]methyl]-2-pyridinyl]-

    10. Enitociclib [inn]

    11. Enitociclib [usan]

    12. Gtpl11686

    13. Glxc-26844

    14. Bdbm50556034

    15. Bay 1251152

    16. Csc(s)-[(2-{[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]amino}pyridin-4-yl)methyl](imino)(methyl)-l6-sulfanone

    2.4 Create Date
    2019-11-19
    3 Chemical and Physical Properties
    Molecular Weight 404.4 g/mol
    Molecular Formula C19H18F2N4O2S
    XLogP34.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count6
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area96.3
    Heavy Atom Count28
    Formal Charge0
    Complexity619
    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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