Plinabulin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202040

CAS#: 714272-27-2

Description: Plinabulin is a VDA of novel structure in having been derived from a marine microbial source, as opposed to terrestrial sources for other VDAs. Plinabulin binds to the colchicine binding site of b-tubulin preventing polymerization and disrupting the cytoplasmic microtubule network. Plinabulin has been shown to produce anti-tumor activity in animal models as a single agent and synergistically with other chemotherapy agents including taxanes. Overall, preclinical studies indicated plinabulin had a favorable safety and activity profile leading to the initiation of clinical trials. Favorable data from early clinical studies lead to the initiation of a Phase 2 clinical trial program. .


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 1950
Size
Price

25mg
USD 150
200mg
USD 750
2g
USD 2950
Size
Price

50mg
USD 250
500mg
USD 1350
5g
USD 4950

Plinabulin, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: Note: the estimated shipping out time for order > 5g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202040
Name: Plinabulin
CAS#: 714272-27-2
Chemical Formula: C19H20N4O2
Exact Mass: 336.15863
Molecular Weight: 336.39
Elemental Analysis: C, 67.84; H, 5.99; N, 16.66; O, 9.51


Synonym: NPI 2358; NPI2358; Plinabulin

IUPAC/Chemical Name: (3E,6E)-3-benzylidene-6-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione

InChi Key: UNRCMCRRFYFGFX-AOEKMSOUSA-N

InChi Code: 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+

SMILES Code: O=C(/C(NC/1=O)=C\C2=CC=CC=C2)NC1=C\C3=C(C(C)(C)C)NC=N3


Technical Data

Appearance:
Yellow solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

 
 
 
 
 
 


References

1: Yakushiji F, Tanaka H, Muguruma K, Iwahashi T, Yamazaki Y, Hayashi Y. Prodrug study of plinabulin using a click strategy focused on the effects of a replaceable water-solubilizing moiety. Chem Pharm Bull (Tokyo). 2012;60(7):877-81. PubMed PMID: 22790821.

2: Yakushiji F, Tanaka H, Muguruma K, Iwahashi T, Yamazaki Y, Hayashi Y. Water-soluble prodrug of antimicrotubule agent plinabulin: effective strategy with click chemistry. Chemistry. 2011 Nov 4;17(45):12587-90. doi: 10.1002/chem.201102293. Epub 2011 Sep 29. PubMed PMID: 21956869.

3: Bertelsen LB, Shen YY, Nielsen T, Stødkilde-Jørgensen H, Lloyd GK, Siemann DW, Horsman MR. Vascular effects of plinabulin (NPI-2358) and the influence on tumour response when given alone or combined with radiation. Int J Radiat Biol. 2011 Nov;87(11):1126-34. doi: 10.3109/09553002.2011.605418. PubMed PMID: 21815749; PubMed Central PMCID: PMC3509771.

4: Singh AV, Bandi M, Raje N, Richardson P, Palladino MA, Chauhan D, Anderson KC. A novel vascular disrupting agent plinabulin triggers JNK-mediated apoptosis and inhibits angiogenesis in multiple myeloma cells. Blood. 2011 May 26;117(21):5692-700. doi: 10.1182/blood-2010-12-323857. Epub 2011 Mar 31. PubMed PMID: 21454451; PubMed Central PMCID: PMC3110026.

5: Millward M, Mainwaring P, Mita A, Federico K, Lloyd GK, Reddinger N, Nawrocki S, Mita M, Spear MA. Phase 1 study of the novel vascular disrupting agent plinabulin (NPI-2358) and docetaxel. Invest New Drugs. 2012 Jun;30(3):1065-73. doi: 10.1007/s10637-011-9642-4. Epub 2011 Feb 16. PubMed PMID: 21327495.

6: Mita MM, Spear MA, Yee LK, Mita AC, Heath EI, Papadopoulos KP, Federico KC, Reich SD, Romero O, Malburg L, Pilat M, Lloyd GK, Neuteboom ST, Cropp G, Ashton E, LoRusso PM. Phase 1 first-in-human trial of the vascular disrupting agent plinabulin(NPI-2358) in patients with solid tumors or lymphomas. Clin Cancer Res. 2010 Dec 1;16(23):5892-9. doi: 10.1158/1078-0432.CCR-10-1096. PubMed PMID: 21138873.

7: Yamazaki Y, Kido Y, Hidaka K, Yasui H, Kiso Y, Yakushiji F, Hayashi Y. Tubulin photoaffinity labeling study with a plinabulin chemical probe possessing a biotin tag at the oxazole. Bioorg Med Chem. 2011 Jan 1;19(1):595-602. doi: 10.1016/j.bmc.2010.10.055. Epub 2010 Oct 31. PubMed PMID: 21106379.

8: Yamazaki Y, Sumikura M, Hidaka K, Yasui H, Kiso Y, Yakushiji F, Hayashi Y. Anti-microtubule 'plinabulin' chemical probe KPU-244-B3 labeled both alpha- and beta-tubulin. Bioorg Med Chem. 2010 May 1;18(9):3169-74. doi: 10.1016/j.bmc.2010.03.037. Epub 2010 Mar 23. PubMed PMID: 20395148.