トセドスタット
Tosedostat
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基本情報
- CAS
238750-77-1- 標準SMILES
CC(C)C[C@@H](C(=O)N[C@H](C(=O)OC1CCCC1)c1ccccc1)[C@H](O)C(=O)NO- InChIKey
FWFGIHPGRQZWIW-SQNIBIBYSA-N- 分子式
- C21H30N2O6
- 平均分子量
- 406.5 g/mol
- 単同位体質量
- 406.21038668
概要
(2S)-2-[[(2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]amino]-2-phenylacetic acid cyclopentyl ester is a secondary carboxamide, a hydroxamic acid and a carboxylic ester.
名称と識別子
- 優先名称
- Tosedostat
- IUPAC
- cyclopentyl (2S)-2-[[(2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-2-phenylacetate
- 現地名
- トセドスタット
- 英語名
- Tosedostat
- 分子式
- C21H30N2O6
- 分子量
- 406.47
名称と別名
Tosedostat238750-77-1CHR 2797CHR-2797CHR2797KZK563J2UWDTXSID60178577Benzeneacetic acid, alpha-(((2R)-2-((1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methyl-1-oxopentyl)amino)-, cyclopentyl ester, (alphaS)-tosedostatumRefChem:898628DTXCID20101068Aminopeptidase inhibitor CHR-2797
名称をさらに表示
トセドスタットシクロペンチル (2S)-2-[(2R,3S)-3-ヒドロキシ-3-(ヒドロキシカルバモイル)-2-(2-メチルプロピル)プロパンアミド]-3-フェニルプロパノアート(S)-2-[[(2R,3S)-2-(2-メチルプロピル)-3-ヒドロキシ-4-オキソ-4-(ヒドロキシアミノ)ブチリル]アミノ]-3-フェニルプロパン酸シクロペンチルCS-2714TosedostaTadalafil: NoCHR2797 (Tosedostat)Tosedostat, 10 mM in DMSO
2-(2-(Hydroxy(hydroxycarbamoyl)methyl)-4-methylpentanoylamino)-2-phenylethanoic acid cyclopentyl esterCYCLOPENTYL (2S)-2-((2R)-2-((1S)-1-HYDROXY-2-(HYDROXYAMINO)-2-OXOETHYL)-4-METHYLPENTANAMIDO)-2-PHENYLACETATEcyclopentyl (2S)-2-((2R,3S)-3-hydroxy-3-(hydroxycarbamoyl)-2-(2-methylpropyl)propanamido)-2-phenylacetateTosedostat (CHR2797)Tosedostat [USAN:INN]MFCD13185162cyclopentyl (S)-2-((R)-2-((S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl)-4-methylpentanamido)-2-phenylacetateBB-76163
物性
構造計算による物性補完中
- XLogP
- 2.3
- 極性表面積
- 125 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 6
- 回転可能結合数
- 10
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 555
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)
- 1.24 · 1.24
- 貯蔵温度
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- 溶解性
- 40.6 mg/mL · ≥40.6 mg/mL in DMSO; insoluble in H2O; ≥15.07 mg/mL in EtOH with ultrasonic
- 外見
- A crystalline solid
- 酸解離定数(Pka)
- 9.44 · 9.44±0.40(Predicted)
- 色
- White to off-white
- InChIKey
- FWFGIHPGRQZWIW-SQNIBIBYSA-N
- SMILES
- CC(C)C[C@H]([C@H](O)C(NO)=O)C(N[C@@H](C1=CC=CC=C1)C(OC2CCCC2)=O)=O
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
- wgk
- WGK 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
PharmacodynamicsTosedostat has pleiotropic effects against a range of human tumor cell lines originating from diverse tumor types in vitro and in vivo.
Mechanism of Action
Tosedostat is anti-proliferative agent which induces apoptosis in leukemic cell lines in vitro. The mechanism underlying these anti-cancer actions is unclear, particularly since normal cells are much less sensitive to the agents than transformed cells. It exerts potent anti-proliferative, pro-apoptotic and anti-angiogenic effects in vitro and shows selectivity for transformed over non-transformed cells. It inhibits a number of M1 aminopeptidase enzyme family members in vitro (eg puromycin-sensitive aminopeptidase (PSA), leukotriene A4 hydrolase (LTA4H)).
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
応用分野
説明Tosedostat is an inhibitor of aminopeptidases (IC50s = 100, 150, and 220 nM for LAP, PUSA, and aminopeptidase N, respectively). It inhibits proliferation of human leukemia cell lines in vitro irrespective of p53, PTEN, or K-RAS mutational status (IC50s = 10-770 nM). Tosedostat induces up-regulation of genes in amino acid transport and metabolic pathways and inhibits phosphorylation of mammalian target of rapamycin (mTOR) substrates in HL-60 cells, markers of amino acid depletion. In vivo, tosedostat (100 mg/kg) reduces total tumor burden and the number of spontaneous metastases in a mouse MDA-MB-435 xenograft model. Formulations containing tosedostat are under clinical investigation for the treatment of myeloid leukemia.
使用Labelled Tosedostat nst a range of tumor cell lines in vitro and in vivo and shows selectivity for transformed over nontransformed cells. Its antiproliferative effects are at least 300 times more potent than the prototyp ical aminopeptidase inhibitor, Bestatin.
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