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    Tolebrutinib

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 1971920-73-6, Prn2246, C]pyridin-2-one, Sar442168, Tolebrutinib [inn], Tolebrutinib [usan]
    Molecular Formula
    C26H25N5O3
    Molecular Weight
    455.5  g/mol
    InChI Key
    KOEUOFPEZFUWRF-LJQANCHMSA-N
    FDA UNII
    8CZ82ZYY9X
    Tolebrutinib is an orally bioavailable, brain-penetrant, selective, small molecule inhibitor of Bruton's tyrosine kinase (BTK), with potential immunomodulatory and anti-inflammatory activities. Upon oral administration, tolebrutinib is able to cross the blood-brain barrier and inhibits the activity of BTK both peripherally and in the central nervous system (CNS). This prevents the activation of the B-cell antigen receptor (BCR) signaling pathway, and the resulting immune activation and inflammation. The inhibition of BTK activity also prevents microglial inflammatory signaling in the CNS, and the resulting immune activation, neuroinflammation and neurodegeneration. BTK, a cytoplasmic tyrosine kinase and member of the Tec family of kinases, plays an important role in B lymphocyte development, activation, signaling, proliferation and survival. In addition to B cells, BTK is also expressed in innate immune cells, including macrophages and microglia, and plays an important role in the regulation of microglial inflammatory signaling.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-3-(4-phenoxyphenyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one
    2.1.2 InChI
    InChI=1S/C26H25N5O3/c1-2-23(32)29-16-6-7-19(17-29)30-22-14-15-28-25(27)24(22)31(26(30)33)18-10-12-21(13-11-18)34-20-8-4-3-5-9-20/h2-5,8-15,19H,1,6-7,16-17H2,(H2,27,28)/t19-/m1/s1
    2.1.3 InChI Key
    KOEUOFPEZFUWRF-LJQANCHMSA-N
    2.1.4 Canonical SMILES
    C=CC(=O)N1CCCC(C1)N2C3=C(C(=NC=C3)N)N(C2=O)C4=CC=C(C=C4)OC5=CC=CC=C5
    2.1.5 Isomeric SMILES
    C=CC(=O)N1CCC[C@H](C1)N2C3=C(C(=NC=C3)N)N(C2=O)C4=CC=C(C=C4)OC5=CC=CC=C5
    2.2 Other Identifiers
    2.2.1 UNII
    8CZ82ZYY9X
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1971920-73-6

    2. Prn2246

    3. C]pyridin-2-one

    4. Sar442168

    5. Tolebrutinib [inn]

    6. Tolebrutinib [usan]

    7. 8cz82zyy9x

    8. Prn-2246

    9. 4-amino-3-(4-phenoxyphenyl)-1-[(3r)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one

    10. (r)-1-(1-acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1h-imidazo[4,5-c]pyridin-2(3h)-one

    11. 4-amino-3-(4-phenoxyphenyl)-1-[(3r)-1-(prop-2-

    12. Enoyl)piperidin-3-yl]-1,3-dihydro-2h-imidazo[4,5-

    13. 2h-imidazo(4,5-c)pyridin-2-one, 4-amino-1,3-dihydro-1-((3r)-1-(1-oxo-2-propen-1-yl)-3-piperidinyl)-3-(4-phenoxyphenyl)-

    14. 4-amino-1,3-dihydro-1-((3r)-1-(1-oxo-2-propen-1-yl)-3-piperidinyl)-3-(4-phenoxyphenyl)-2h-imidazo(4,5-c)pyridin-2-one

    15. Unii-8cz82zyy9x

    16. Tolebrutinib [who-dd]

    17. Chembl4650323

    18. Schembl18285621

    19. Gtpl10625

    20. Btk'168

    21. Ex-a4699

    22. Bdbm50557487

    23. Who 11268

    24. Sar-442168

    25. Example 3 [wo2016196840a1]

    26. Sar442168; Prn2246

    27. Hy-109192

    28. Cs-0119132

    2.4 Create Date
    2017-02-18
    3 Chemical and Physical Properties
    Molecular Weight 455.5 g/mol
    Molecular Formula C26H25N5O3
    XLogP33.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass455.19573968 g/mol
    Monoisotopic Mass455.19573968 g/mol
    Topological Polar Surface Area92 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity749
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1