WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202040
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. .
MedKoo Cat#: 202040
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; NPI-2358; 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
Appearance: Yellow solid powder
Purity: >98% (or refer to the Certificate of Analysis)
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 336.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
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, StÃ¸dkilde-JÃ¸rgensen 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.