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Plinabulin

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Chemistry

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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

Plinabulin

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 Formula	C₁₉H₂₀N₄O₂
Molecular Weight	336.4 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	336.15862589 g/mol
Monoisotopic Mass	336.15862589 g/mol
Topological Polar Surface Area	86.9 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	597
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

Drugs in Development