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Plinabulin

CAT: 0804-HY-14444-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-14444-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Plinabulin (NPI-2358) is a vascular disrupting agen (VDA) against tubulin-depolymerizing with an IC50 of 9.8 nM against HT-29 cells[1]. Plinabulin binds the colchicine binding site of β-tubulin preventing polymerization and has potent inhibitory to tumor cells[2].
CAS Number
714272-27-2
Product Name Alternative
NPI-2358
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Microtubule/Tubulin
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage; Cytoskeleton
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/plinabulin.html
Purity
98.0
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C(N/C1=C\C2=C(NC=N2)C(C)(C)C)/C(NC1=O)=C/C3=CC=CC=C3
Molecular Formula
C19H20N4O2
Molecular Weight
336.39
Precautions
H302, H315, H319, H335
References & Citations
[1]Nicholson B et al. NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anticancer Drugs. 2006 Jan;17 (1) :25-31.|[2]Monica M. Mita et al. 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.|[3]Bertelsen LB, et al. 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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 3

Chemical Information

Plinabulin

Plinabulin is a member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione substituted by benzylidene and (5-tert-butyl-1H-imidazol-4-yl)methylidene groups at positions 3 and 6, respectively. It is a vascular disrupting agent and a microtubule destabalising agent which was in clinical trials (now discontinued) for the treatment of non-small cell lung cancer. It has a role as an antineoplastic agent, an angiogenesis inhibitor, a microtubule-destabilising agent and an apoptosis inducer. It is a member of benzenes, a member of imidazoles, a member of 2,5-diketopiperazines and an olefinic compound.

CAS Number714272-27-2
PubChem CID9949641
IUPAC Name(3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
Molecular FormulaC19H20N4O2
Molecular Weight336.4
XLogP2.8
Topological Polar Surface Area86.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Heavy Atom Count25
Formal Charge0
Complexity597
SMILES
CC(C)(C)C1=C(N=CN1)/C=C\2/C(=O)N/C(=C\C3=CC=CC=C3)/C(=O)N2
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-
InChIKey
UNRCMCRRFYFGFX-TYPNBTCFSA-N
Chemical Structure
2D Structure
2D structure of Plinabulin
CAS: 714272-27-2
CID: 9949641
Formula: C19H20N4O2
MW: 336.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight336.4
XLogP32.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass336.15862589
Monoisotopic Mass336.15862589
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
Compound Is CanonicalizedYes

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CatalogName
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B2298-100Plinabulin (NPI-2358)

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