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    Navoximod

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 1402837-78-8, Ido-in-7, Gdc-0919, Navoximod [usan], Navoximod (free base), Nlg-919
    Molecular Formula
    C18H21FN2O2
    Molecular Weight
    316.4  g/mol
    InChI Key
    YGACXVRLDHEXKY-LHPNLFKDSA-N
    FDA UNII
    926SHL95NC
    Navoximod is an orally available inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1), with potential immunomodulating and antineoplastic activities. Upon administration, navoximod targets and binds to IDO1, a cytosolic enzyme responsible for the oxidation of the essential amino acid tryptophan into kynurenine. By inhibiting IDO1 and decreasing kynurenine in tumor cells, this agent increases tryptophan levels, restores the proliferation and activation of various immune cells, including dendritic cells (DCs), natural killer (NK) cells, and T-lymphocytes, and causes a reduction in tumor-associated regulatory T-cells (Tregs). Activation of the immune system, which is suppressed in many cancers, may induce a cytotoxic T-lymphocyte (CTL) response against the IDO1-expressing tumor cells. IDO1 is overexpressed by a variety of tumor cell types and plays an important role in immunosuppression. Tryptophan depletion is associated with immunosuppression caused by T-cell suppression.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(1R)-2-[(5S)-6-fluoro-5H-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl]cyclohexan-1-ol
    2.1.2 InChI
    InChI=1S/C18H21FN2O2/c19-14-3-1-2-13-16-9-20-10-21(16)15(18(13)14)8-17(23)11-4-6-12(22)7-5-11/h1-3,9-12,15,17,22-23H,4-8H2/t11?,12?,15-,17+/m0/s1
    2.1.3 InChI Key
    YGACXVRLDHEXKY-LHPNLFKDSA-N
    2.1.4 Canonical SMILES
    C1CC(CCC1C(CC2C3=C(C=CC=C3F)C4=CN=CN24)O)O
    2.1.5 Isomeric SMILES
    C1CC(CCC1[C@@H](C[C@H]2C3=C(C=CC=C3F)C4=CN=CN24)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    926SHL95NC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5h-imidazo(5,1-a)isoindole-5-ethanol, 6-fluoro-alpha-(trans-4-hydroxycyclohexyl)-, (alphar,5s)-

    2. Gdc-0919

    3. Trans-4-((1r)-2-((5s)-6-fluoro-5h-imidazo(5,1-a)isoindol-5-yl)-1-hydroxyethyl)cyclohexanol

    2.3.2 Depositor-Supplied Synonyms

    1. 1402837-78-8

    2. Ido-in-7

    3. Gdc-0919

    4. Navoximod [usan]

    5. Navoximod (free Base)

    6. Nlg-919

    7. 926shl95nc

    8. Ro7077339-001

    9. Rg6078

    10. Rg-6078

    11. Ro7077339

    12. Ro-7077339

    13. 4-[(1r)-2-[(5s)-6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl]cyclohexan-1-ol

    14. Trans-4-((1r)-2-((5s)-6-fluoro-5h-imidazo(5,1-a)isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol

    15. Trans-4-{(1r)-2-[(5s)-6-fluoro-5h-imidazo[5,1-a]isoindol-5-yl]-1-hydroxyethyl}cyclohexan-1-ol

    16. Nlg-919 Navoximod

    17. Navoximod [inn]

    18. Navoximod (usan/inn)

    19. Navoximod [who-dd]

    20. Unii-926shl95nc

    21. Chembl3989951

    22. Chembl4530496

    23. Schembl13469854

    24. Schembl13469866

    25. Schembl15511408

    26. Bdbm370551

    27. Bdbm370555

    28. Ex-a4607

    29. Nlg-?919

    30. Nlg-?919gdc-0919

    31. Hy-18770b

    32. S8957

    33. Zinc253387955

    34. Cs-5088

    35. Db15439

    36. Us10233190, Example 1484

    37. Us10233190, Example 1488

    38. Ac-35763

    39. D11255

    40. Navoximod;gdc-0919;ido-in-7;nlg-1488

    41. Q27271481

    42. (1r,4r)-4-((r)-2-((s)-6-fluoro-5h-imidazo[5,1- A]isoindol-5-yl)-1-hydroxyethyl)cyclohexanol

    43. (1s,4s)-4-((r)-2-((s)-6-fluoro-5h-imidazo[5,1- A]isoindol-5-yl)-1-hydroxyethyl)cyclohexanol

    44. 1402836-86-5

    45. 5h-imidazo(5,1-a)isoindole-5-ethanol, 6-fluoro-.alpha.-(trans-4-hydroxycyclohexyl)-, (.alpha.r,5s)-

    46. 5h-imidazo(5,1-a)isoindole-5-ethanol, 6-fluoro-alpha-(trans-4-hydroxycyclohexyl)-, (alphar,5s)-

    47. Trans-4-((1r)-2-((5s)-6-fluoro-5h-imidazo(5,1-a)isoindol-5-yl)-1-hydroxyethyl)cyclohexanol

    2.4 Create Date
    2013-03-21
    3 Chemical and Physical Properties
    Molecular Weight 316.4 g/mol
    Molecular Formula C18H21FN2O2
    XLogP32.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass316.15870608 g/mol
    Monoisotopic Mass316.15870608 g/mol
    Topological Polar Surface Area58.3 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity416
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1