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    Opaganib

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    DIGITAL CONTENT

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    2D Structure
    Also known as: Abc294640, Opaganib, 915385-81-8, Abc-294640, Abc 294640, Chembl2158685
    Molecular Formula
    C23H25ClN2O
    Molecular Weight
    380.9  g/mol
    InChI Key
    CAOTVXGYTWCKQE-UHFFFAOYSA-N
    FDA UNII
    DRG21OQ517
    Opaganib is an orally available, aryladamantane compound and selective inhibitor of sphingosine kinase-2 (SK2) with potential antineoplastic activity. Upon administration, opaganib competitively binds to and inhibits SK2, thereby preventing the phosphorylation of the pro-apoptotic amino alcohol sphingosine to sphingosine 1-phosphate (S1P), the lipid mediator that is pro-survival and critical for immunomodulation. This may eventually lead to the induction of apoptosis and may result in an inhibition of cell proliferation in cancer cells overexpressing SK2. SK2 and its isoenzyme SK1 are overexpressed in numerous cancer cell types.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)adamantane-1-carboxamide
    2.1.2 InChI
    InChI=1S/C23H25ClN2O/c24-20-3-1-19(2-4-20)22-10-17-9-18(11-22)13-23(12-17,15-22)21(27)26-14-16-5-7-25-8-6-16/h1-8,17-18H,9-15H2,(H,26,27)
    2.1.3 InChI Key
    CAOTVXGYTWCKQE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1C2CC3(CC1CC(C2)(C3)C(=O)NCC4=CC=NC=C4)C5=CC=C(C=C5)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    DRG21OQ517
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-(4-chlorophenyl)-adamantane-1-carboxylic Acid (pyridin-4-ylmethyl)amide

    2. 4-pyridinylmethyl-3-(4-chlorophenyl) Adamantane Carboxamide

    3. Abc 294640

    4. Abc-294640

    5. Abc294640

    2.3.2 Depositor-Supplied Synonyms

    1. Abc294640

    2. Opaganib

    3. 915385-81-8

    4. Abc-294640

    5. Abc 294640

    6. Chembl2158685

    7. 4-pyridinylmethyl-3-(4-chlorophenyl) Adamantane Carboxamide

    8. Drg21oq517

    9. Yeliva

    10. Tricyclo(3.3.1.13,7)decane-1-carboxamide, 3-(4-chlorophenyl)-n-(4-pyridinylmethyl)-

    11. Abc294640opaganib

    12. Opaganib [inn]

    13. Opaganib [who-dd]

    14. Opaganib (abc294640)

    15. Gtpl6624

    16. Schembl1548333

    17. Chebi:124965

    18. Dtxsid801318727

    19. Hms3402p05

    20. Amy42174

    21. Bcp08959

    22. Ex-a1962

    23. Bdbm50393642

    24. Nsc796101

    25. Akos027327311

    26. Ccg-268417

    27. Cs-0877

    28. Db12764

    29. Nsc-796101

    30. Sb17167

    31. Ac-33116

    32. As-56117

    33. Ba162479

    34. Hy-16015

    35. S7174

    36. Brd-a70814879-003-01-8

    37. Q27074100

    38. Abc294640

    39. 915385-81-8

    40. Abc-294640

    41. 4-pyridinylmethyl 3(4-chlorophenyl)adamantine Carboxamide

    42. (1s,3r,5r,7s)-3-(4-chlorophenyl)-n-(pyridin-4-ylmethyl)adamantane-1-carboxamide

    2.4 Create Date
    2007-02-12
    3 Chemical and Physical Properties
    Molecular Weight 380.9 g/mol
    Molecular Formula C23H25ClN2O
    XLogP34.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count4
    Exact Mass380.1655411 g/mol
    Monoisotopic Mass380.1655411 g/mol
    Topological Polar Surface Area42 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity551
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Mechanism of Action

    Opaganib selectively inhibits [sphingosine kinase-2 (SK2)](https://go.drugbank.com/polypeptides/Q9NRA0). This inhibition blocks the synthesis of sphingosine 1-phosphate (S1P) and its activities (which includes regulation of fundamental biological processes such as cell proliferation, migration, immune cell trafficking, angiogenesis, immune-modulation, and suppression of innate immune responses from T-cells). This drug has dual anti-inflammatory and antiviral activity targeting a host cell component and is unaffected by viral mutation, contributing to minimization of the likelihood of resistance. It is currently being investigated against COVID-19 as it has demonstrated anti-SARS-CoV-2 activity in studies.