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    Eganelisib

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    DIGITAL CONTENT

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    2D Structure
    Also known as: Ipi-549, 1693758-51-8, Eganelisib [usan], Pi3k-gamma inhibitor ipi-549, Fof5155fmz, Ipi549
    Molecular Formula
    C30H24N8O2
    Molecular Weight
    528.6  g/mol
    InChI Key
    XUMALORDVCFWKV-IBGZPJMESA-N
    FDA UNII
    FOF5155FMZ
    Eganelisib is an orally bioavailable, highly selective small molecule inhibitor of the gamma isoform of phosphoinositide-3 kinase (PI3K-gamma) with potential immunomodulating and antineoplastic activities. Upon administration, eganelisib prevents the activation of the PI3K-gamma-mediated signaling pathways, which may lead to a reduction in cellular proliferation in PI3K-gamma-expressing tumor cells. In addition, this agent is able to modulate anti-tumor immune responses and inhibit tumor-mediated immunosuppression. Unlike other isoforms of PI3K, the gamma isoform is overexpressed in certain tumor cell types and immune cells; its expression increases tumor cell proliferation and survival. By selectively targeting the gamma isoform, PI3K signaling in normal, non-neoplastic cells is minimally or not affected, which results in a reduced side effect profile.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide
    2.1.2 InChI
    InChI=1S/C30H24N8O2/c1-19(34-29(39)26-27(31)35-37-15-7-14-32-28(26)37)24-16-22-9-6-8-21(13-12-20-17-33-36(2)18-20)25(22)30(40)38(24)23-10-4-3-5-11-23/h3-11,14-19H,1-2H3,(H2,31,35)(H,34,39)/t19-/m0/s1
    2.1.3 InChI Key
    XUMALORDVCFWKV-IBGZPJMESA-N
    2.1.4 Canonical SMILES
    CC(C1=CC2=C(C(=CC=C2)C#CC3=CN(N=C3)C)C(=O)N1C4=CC=CC=C4)NC(=O)C5=C6N=CC=CN6N=C5N
    2.1.5 Isomeric SMILES
    C[C@@H](C1=CC2=C(C(=CC=C2)C#CC3=CN(N=C3)C)C(=O)N1C4=CC=CC=C4)NC(=O)C5=C6N=CC=CN6N=C5N
    2.2 Other Identifiers
    2.2.1 UNII
    FOF5155FMZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-amino-n-((1s)-1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2-dihydro-3-isoquinolinyl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

    2. Ipi-549

    2.3.2 Depositor-Supplied Synonyms

    1. Ipi-549

    2. 1693758-51-8

    3. Eganelisib [usan]

    4. Pi3k-gamma Inhibitor Ipi-549

    5. Fof5155fmz

    6. Ipi549

    7. Chembl3984425

    8. 2-amino-n-[(1s)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

    9. (s)-2-amino-n-(1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2- Dihydroisoquinolin-3-yl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

    10. 2-amino-n-[(1s)-1-{8-[(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl}ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

    11. Pyrazolo(1,5-a)pyrimidine-3-carboxamide, 2-amino-n-((1s)-1-(1,2-dihydro-8-(2-(1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-3-isoquinolinyl)ethyl)-

    12. Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 2-amino-n-[(1s)-1-[1,2-dihydro-8-[2-(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl-3-isoquinolinyl]ethyl]-

    13. Eganelisib [inn]

    14. Unii-fof5155fmz

    15. Eganelisib [who-dd]

    16. Gtpl9563

    17. Schembl16629991

    18. Dtxsid301336580

    19. Ipi-549(ipi549)

    20. Amy16733

    21. Ex-a1057

    22. V7y

    23. Bdbm50192880

    24. Mfcd30533720

    25. Nsc795067

    26. Nsc801002

    27. S8330

    28. Who 11571

    29. Zinc584906867

    30. Ccg-269905

    31. Cs-6106

    32. Nsc-795067

    33. Nsc-801002

    34. Compound 26 [pmid: 27660692]

    35. Ac-29898

    36. As-55938

    37. Hy-100716

    38. A16332

    39. 2-amino-n-((1s)-1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2-dihydro-3-isoquinolinyl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

    40. 2-amino-n-[(1s)-1-{8-[2-(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl- 1,2-dihydroisoquinolin-3-yl}ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

    2.4 Create Date
    2015-10-12
    3 Chemical and Physical Properties
    Molecular Weight 528.6 g/mol
    Molecular Formula C30H24N8O2
    XLogP33.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass528.20222204 g/mol
    Monoisotopic Mass528.20222204 g/mol
    Topological Polar Surface Area123 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity1060
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1