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    Plinabulin

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 714272-27-2, Npi-2358, Plinabulin (npi-2358), Plinabulin(npi-2358), Npi-2358 (plinabulin), Npi 2358
    Molecular Formula
    C19H20N4O2
    Molecular Weight
    336.4  g/mol
    InChI Key
    UNRCMCRRFYFGFX-TYPNBTCFSA-N
    FDA UNII
    986FY7F8XR
    Plinabulin is an orally active diketopiperazine derivative with potential antineoplastic activity. Plinabulin selectively targets and binds to the colchicine-binding site of tubulin, thereby interrupting equilibrium of microtubule dynamics. This disrupts mitotic spindle assembly leading to cell cycle arrest at M phase and blockage of cell division. In addition, plinabulin may also inhibit growth of proliferating vascular endothelial cells, thereby disrupting the function of tumor vasculature that further contributes to a decrease in tumor cell proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
    2.1.2 InChI
    InChI=1S/C19H20N4O2/c1-19(2,3)16-13(20-11-21-16)10-15-18(25)22-14(17(24)23-15)9-12-7-5-4-6-8-12/h4-11H,1-3H3,(H,20,21)(H,22,25)(H,23,24)/b14-9-,15-10-
    2.1.3 InChI Key
    UNRCMCRRFYFGFX-TYPNBTCFSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C1=C(N=CN1)C=C2C(=O)NC(=CC3=CC=CC=C3)C(=O)N2
    2.1.5 Isomeric SMILES
    CC(C)(C)C1=C(N=CN1)/C=C\2/C(=O)N/C(=C\C3=CC=CC=C3)/C(=O)N2
    2.2 Other Identifiers
    2.2.1 UNII
    986FY7F8XR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Mbri-001

    2. Npi 2358

    3. Npi-2358

    4. Npi2358

    2.3.2 Depositor-Supplied Synonyms

    1. 714272-27-2

    2. Npi-2358

    3. Plinabulin (npi-2358)

    4. Plinabulin(npi-2358)

    5. Npi-2358 (plinabulin)

    6. Npi 2358

    7. (3z,6z)-3-benzylidene-6-[(5-tert-butyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione

    8. 986fy7f8xr

    9. Npi2358

    10. (3e,6e)-3-benzylidene-6-[(5-tert-butyl-1h-imidazol-4-yl)methylidene]piperazine-2,5-dione

    11. (3z,6z)-3-benzylidene-6-((5-(tert-butyl)-1h-imidazol-4-yl)methylene)piperazine-2,5-dione

    12. 2,5-piperazinedione, 3-((5-(1,1-dimethylethyl)-1h-imidazol-4-yl)methylene)-6-(phenylmethylene)-, (3z,6z)-

    13. Plinabulin [usan:inn]

    14. Plinabulina

    15. Plinabuline

    16. Plinabulinum

    17. Unii-986fy7f8xr

    18. Plinabulin [mi]

    19. Plinabulin [inn]

    20. Plinabulin (usan/inn)

    21. Plinabulin [usan]

    22. Kpu-2

    23. Plinabulin [who-dd]

    24. Schembl79095

    25. Mls006011262

    26. Chembl1096380

    27. Ex-a292

    28. Chebi:177413

    29. Dtxsid201031311

    30. Bpi 2358

    31. Bpi-2358

    32. Zinc3819466

    33. Bdbm50030765

    34. Mfcd18074510

    35. Nsc797934

    36. S1176

    37. Akos005145762

    38. Akos024463284

    39. Bcp9000994

    40. Ccg-264849

    41. Cs-0506

    42. Db05992

    43. Nsc-797934

    44. Ac-32812

    45. Hy-14444

    46. Smr004703013

    47. Bcp0726000116

    48. Sw219827-1

    49. D09655

    50. Brd-k99498722-001-01-8

    51. Q15269699

    52. (3z,6z)-6-benzylidene-3-((5-(1,1-dimethylethyl)-1h-imidazol-4- Yl)methylidene)piperazine-2,5-dione

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 336.4 g/mol
    Molecular Formula C19H20N4O2
    XLogP32.8
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass336.15862589 g/mol
    Monoisotopic Mass336.15862589 g/mol
    Topological Polar Surface Area86.9 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity597
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in cancer/tumors (unspecified).

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    NPI-2358 is a vascular disrupting agent currently in clinical development for the treatment of cancer by Nereus. NPI-2358 is one of over 200 synthetic analogues that were prepared following the discovery of the compound Halimide isolated from a marine fungus. In preclinical models of cancer, including lung, breast, sarcoma, colon and prostate, NPI-2358 demonstrated potent and selective anti-tumor effects in combination with docetaxel and other oncology therapies, as well as single-agent efficacy in a number of orthotopic models. NPI-2358 interacts with soluble beta-tubulin and prevents the polymerization of tubulin without altering dynamic microtubule function of formed microtubules. As demonstrated in preclinical testing, this target profile results in a highly specific nanomolar cytotoxicity while reducing the side effects seen in first-generation VDAs due to cardiotoxicity, hemodynamic changes and neuropathies.