基本情報
- CAS
714272-27-2- 標準SMILES
CC(C)(C)c1[nH]cnc1/C=c1\[nH]c(=O)/c(=C/c2ccccc2)[nH]c1=O- InChIKey
UNRCMCRRFYFGFX-TYPNBTCFSA-N- 分子式
- C19H20N4O2
- 平均分子量
- 336.4 g/mol
- 単同位体質量
- 336.15862589
概要
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.
名称と識別子
- 優先名称
- Plinabulin
- IUPAC
- (3Z,6Z)-3-benzylidene-6-[(5-tert-butyl-1H-imidazol-4-yl)methylidene]piperazine-2,5-dione
- 現地名
- プリナブリン
- 英語名
- Plinabulin(NPI-2358)
- 分子式
- C19H20N4O2
- 分子量
- 336.39
名称と別名
Plinabulin714272-27-2NPI-2358plinabulinaplinabulineplinabulinumNPI 2358986FY7F8XRNPI23582,5-Piperazinedione, 3-((5-(1,1-dimethylethyl)-1H-imidazol-4-yl)methylene)-6-(phenylmethylene)-, (3Z,6Z)-CHEBI:177413DTXSID201031311
名称をさらに表示
プリナブリン2-[(Z)-ベンジリデン]-5-[(Z)-(5-tert-ブチル-1H-イミダゾール)-4-イルメチレン]ピペラジン-3,6-ジオン(3Z,6Z)-3-[(5-tert-ブチル-1H-イミダゾール-4-イル)メチリデン]-6-(フェニルメチリデン)ピペラジン-2,5-ジオンCS-829EOS-62083NSC406141NSC 406141NSC-406141Plinabulin, >=98%Plinabulin(NPI-2358)
RefChem:863841DTXCID101516316(3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylidene)-6-(phenylmethylidene)piperazine-2,5-dione(3Z,6Z)-6-BENZYLIDENE-3-((5-(1,1-DIMETHYLETHYL)-1H-IMIDAZOL-4-YL)METHYLIDENE)PIPERAZINE-2,5-DIONEPlinabulin (NPI-2358)Plinabulin [USAN:INN](3z,6z)-3-Benzylidene-6-[(5-Tert-Butyl-1h-Imidazol-4-Yl)methylidene]piperazine-2,5-DioneUNII-986FY7F8XR
データベース識別子
- CAS
物性
構造計算による物性
- XLogP
- 2.8
- 極性表面積
- 86.9 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 3
- 回転可能結合数
- 3
- 重原子数
- 25
- 形式電荷
- 0
- 複雑度
- 597
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
物理化学的性質
- 比重(密度)
- 1.267 · 1.267
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- Soluble in DMSO
- 外見
- Powder
- 色
- Light yellow to yellow
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- 注意喚起語
- 警告
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302
化学と産業
薬理情報
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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