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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
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 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.


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Looking for 714272-27-2 / Plinabulin API manufacturers, exporters & distributors?

Plinabulin manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Plinabulin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Plinabulin manufacturer or Plinabulin supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Plinabulin manufacturer or Plinabulin supplier.

PharmaCompass also assists you with knowing the Plinabulin API Price utilized in the formulation of products. Plinabulin API Price is not always fixed or binding as the Plinabulin Price is obtained through a variety of data sources. The Plinabulin Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Plinabulin

Synonyms

714272-27-2, Npi-2358, Plinabulin (npi-2358), Plinabulin(npi-2358), Npi-2358 (plinabulin), Npi 2358

Cas Number

714272-27-2

Unique Ingredient Identifier (UNII)

986FY7F8XR

About Plinabulin

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.

Plinabulin Manufacturers

A Plinabulin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Plinabulin, including repackagers and relabelers. The FDA regulates Plinabulin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Plinabulin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Plinabulin Suppliers

A Plinabulin supplier is an individual or a company that provides Plinabulin active pharmaceutical ingredient (API) or Plinabulin finished formulations upon request. The Plinabulin suppliers may include Plinabulin API manufacturers, exporters, distributors and traders.

Plinabulin GMP

Plinabulin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Plinabulin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Plinabulin GMP manufacturer or Plinabulin GMP API supplier for your needs.

Plinabulin CoA

A Plinabulin CoA (Certificate of Analysis) is a formal document that attests to Plinabulin's compliance with Plinabulin specifications and serves as a tool for batch-level quality control.

Plinabulin CoA mostly includes findings from lab analyses of a specific batch. For each Plinabulin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Plinabulin may be tested according to a variety of international standards, such as European Pharmacopoeia (Plinabulin EP), Plinabulin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Plinabulin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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