基本情報
- CAS
192755-52-5- 標準SMILES
CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]1CCCN2C(=O)CC[C@H](NC(=O)c3nccc4ccccc34)C(=O)N12- InChIKey
CXAGHAZMQSCAKJ-WAHHBDPQSA-N- 分子式
- C26H29N5O7
- 平均分子量
- 523.5 g/mol
- 単同位体質量
- 523.20669828
概要
Pralnacasan is an orally bioavailable pro-drug of a potent, non-peptide inhibitor of interleukin-1beta converting enzyme (ICE).
名称と識別子
- 優先名称
- Pralnacasan
- IUPAC
- (4S,7S)-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]-7-(isoquinoline-1-carbonylamino)-6,10-dioxo-2,3,4,7,8,9-hexahydro-1H-pyridazino[1,2-a]diazepine-4-carboxamide
- 現地名
- プラルナカサン
- 英語名
- (3S,11S)-N-[(2R,3S)-2-ethoxy-5-oxo-oxolan-3-yl]-3-(isoquinoline-1-carbonylamino)-2,6-dioxo-1,7-diazabicyclo[5.4.0]undecane-11-carboxamide
- 分子式
- C26H29N5O7
- 分子量
- 523.54
名称と別名
Pralnacasan192755-52-5VX-740HMR3480HMR-3480HMR3480/VX-740N986NI319SHMR-3480/VX-740DTXSID60172873(1S,9S)-N-((2R,3S)-2-Ethoxy-5-oxotetrahydrofuran-3-yl)-9-((isoquinolin-1-ylcarbonyl)amino)-6,10-dioxooctahydro-6-H-pyridazino(1,2-a)(1,2)diazepine-1-carboxamidepralnacasanum(1S,9S)-N-((2R,3S)-2-ethoxy-5-oxooxolan-3-yl)-9-(isoquinoline-1-carbonylamino)-6,10-dioxo-2,3,4,7,8,9-hexahydro-1H-pyridazino(1,2-a)diazepine-1-carboxamide
名称をさらに表示
プラルナカサンN-[(3S)-テトラヒドロ-2β-エトキシ-5-オキソフラン-3-イル]オクタヒドロ-6,10-ジオキソ-9α-[(イソキノリン-1-イルカルボニル)アミノ]-6H-ピリダジノ[1,2-a][1,2]ジアゼピン-1α-カルボアミドN-[(4S,7S)-4-{[(2R,3S)-2-エトキシ-5-オキソオキソラン-3-イル]カルバモイル}-6,10-ジオキソ-オクタヒドロ-1H-ピリダジノ[1,2-a][1,2]ジアゼピン-7-イル]イソキノリン-1-カルボキサミドHMR 3480(3S,11S)-N-[(2R,3S)-2-ethoxy-5-oxo-oxolan-3-yl]-3-(isoquinoline-1-carbonylamino)-2,6-dioxo-1,7-diazabicyclo[5.4.0]undecane-11-carboxamide(1S,9S)-N-[(2R,3S)-2-Ethoxy-5-oxotetrahydro-3-furanyl]-9-[(1-isoquinolinylcarbonyl)amino]-6,10-dioxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide
物性
構造計算による物性
- XLogP
- 0.9
- 極性表面積
- 147 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 6
- 重原子数
- 38
- 形式電荷
- 0
- 複雑度
- 960
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.16
物理化学的性質
- 比重(密度)
- 1.44 · 1.44±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Store at -20°C
- 外見
- Solid
- 酸解離定数(Pka)
- 10.8 · 10.80±0.40(Predicted)
- 色
- White to off-white
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。
毒性情報
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Pralnacasan
vMost-DILI-concern
8
Discontinued
DOI:10.1016/j.drudis.2016.02.015
化学と産業
薬理情報
Pharmacodynamics
Pralnacasan is a potent, non-peptide inhibitor of interleukin-1beta converting enzyme (ICE). Pralnacasan is an oral, anti-cytokine drug candidate licensed for development by Aventis Pharma from Vertex Pharmaceuticals. In November 2003, Aventis and Vertex Pharmaceuticals announced that they had voluntarily suspended the phase II clinical trials of pralnacasan due to results from an animal toxicity study that demonstrated liver abnormalities after a nine-month exposure to pralnacasan at high doses. While no similar liver toxicity has been seen to date in human trials, the companies will evaluate the animal toxicity results before proceeding with the phase II clinical program.
Mechanism of Action
Pralnacasan inhibits interleukin-1beta converting enzyme (ICE), an enzyme that regulates the production of IL-1 and IFN gamma - intercellular mediators that initiate and sustain the process of inflammation. Inhibiting ICE may be an effective strategy for curtailing damaging inflammatory processes common to a number of acute and chronic conditions, such as rheumatoid arthritis (RA) and osteoarthritis.
Absorption, Distribution and ExcretionOrally bioavailable
応用分野
使用Treatment of rheumatoid arthritis; (interleukin-1β converting enzyme (also known as caspase- 1) inhibitor).
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