基本情報
- CAS
60940-34-3- 標準SMILES
O=c1c2ccccc2[se]n1-c1ccccc1- InChIKey
DYEFUKCXAQOFHX-UHFFFAOYSA-N- 分子式
- C13H9NOSe
- 平均分子量
- 274.19 g/mol
- 単同位体質量
- 274.98494
概要
Ebselen is a benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase. It has a role as an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, a ferroptosis inhibitor, an EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor, an antioxidant, an antibacterial agent, an anti-inflammatory drug, an antineoplastic agent, an antifungal agent, a radical scavenger, a genotoxin, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor, a hepatoprotective agent, a neuroprotective agent, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an apoptosis inducer, an EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor, an enzyme mimic, an EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor, an EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor, an EC 3.5.4.1 (cytosine deaminase) inhibitor and an EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor.
名称と識別子
- 優先名称
- Ebselen
- IUPAC
- 2-phenyl-1,2-benzoselenazol-3-one
- 現地名
- 2-フェニル-1-セレナ-2H-イソインドール-3(1H)-オン
- 英語名
- Ebselen
- 分子式
- C13H9NOSe
- 分子量
- 274.18
名称と別名
ebselen60940-34-32-Phenyl-1,2-benzisoselenazol-3(2H)-one2-phenyl-1,2-benzoselenazol-3-oneEbselenumEbseleneEbselenoSPI-1005PZ 51PZ-51DR-3305DR3305
名称をさらに表示
2-フェニル-1-セレナ-2H-イソインドール-3(1H)-オン2-フェニル-1,2-ベンゾイソセレナゾール-3(2H)-オン2-フェニル-1-セレナ-2-アザインダン-3-オン2-フェニル-3H-1,2-ベンゾイソセレナゾール-3-オンエブセレンエブゼレン2-フェニル-2,3-ジヒドロ-1,2-ベンゾイソセレナゾール-3-オン2-フェニル-2,3-ジヒドロ-1-セレナ-2-アザ-1H-インデン-3-オン2-フェニル-1-セレナイソインドリン-3-オンエブセン2-フェニル-2,3-ジヒドロ-1,2-ベンゾセレナゾール-3-オン2-フェニル-3-セレナイソインドリン-1-オン2-フェニル-1-セレナ-2-アザ-1H-インデン-3(2H)-オン2-フェニル-3H-1-セレナ-2H-イソインドール-3-オンPZ51RP-60931CCG-39161NSC 639762Ebselen>Ebselen,99%
2-phenyl-1,2-benzoisoselenazol-3(2H)-oneDTXSID704515040X2P7DPGHNSC-639762NSC-7578832-phenyl-2,3-dihydro-1,2-benzoselenazol-3-oneSPI1005SPI 1005
物性
構造計算による物性
- 極性表面積
- 20.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 1
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 275
実験および物理化学的性質
Solubility
6.6 [ug/mL] (The mean of the results at pH 7.4)
13.6 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section
145.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
145.11 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 176 · 176-182 °C
- 沸点
- 402.8 · 402.8±28.0 °C(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- エタノール、メタノール、アセトン、アセトニトリルに可溶。
- 酸解離定数(Pka)
- -0.4 · -0.40±0.20(Predicted)
- 外見
- 結晶性粉末
- 色
- 黄色からベージュ
- 由来生物
- rabbit
- Merck
- 14 · 14,3486
- 安定性
- -20 °Cで最大3か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大3か月保存できます。
- InChI
- InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
- InChIKey
- DYEFUKCXAQOFHX-UHFFFAOYSA-N
- SMILES
- [Se]1C2=C(C=CC=C2)C(=O)N1C1=CC=CC=C1
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。
GHS分類
GHS Classification
Danger
H301 (95.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P319, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (95.6%)
安全データ
- wgk
- 3
- rtecs
- DE4140750
- ridadr
- UN 3283 6.1/PG 3
- PRTR法
- 第一種指定化学物質
- hs_code
- 29310099
- risk_code
- 23/25-33-50/53-36/37/38
- 安衛法
- 57-2
- hazard_code
- T,N,Xi
- safety_code
- 20/21-28-45-60-61-28A-36/37-26
- hazard_class
- 6.1
- packing_group
- III
- 毒劇物取締法
- 毒物
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
- ストレージクラス
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
化学と産業
薬理情報
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
応用分野
用途医薬品，抗炎症作用
説明Ebselen is one of the selenium-containing anti-inflammatory drugs.In 2003, Rocha and co-workers identified diselenides as a new class of antiinflammatory agents.In 2014, Nogueira and co-workers reported the synthesis and anti-inflammatory activity of salicyclic-based diselenides and selenocynates.Recently, Wilhelm and co-workers identified 4-phenylselenyl-7-chloroquinoline 270 as a potent antiinflammatory compound.
使用Ebselen is a lipid-soluble organoselenium compound. Numerous in vivo experiments have demonstrated that ebselen is able to inhibit both vasospasm and tissue damage in cerebral stroke/ischemia animal models (i.e. rat, mice, guinea pig and dog).For example, ebselen has been shown to provide significant protection against ischemic damage in both gray and white matter, and in the ventral posterior nucleus of rodent brains.Additionally, administration of ebselen in gerbils significantly reduces neuronal death induced by ischemia and reperfusion in the hippocampal CA1 region.It has been reported that ebselen inhibits inositol monophosphatase and acts as a safe treatment for bipolar disorder. The optimal GPx-like activity of ebselen was observed at neutral or nearphysiological pH (7.4), and the activity of ebselen was barely detected in acidic medium.During ischemia, brain pH falls rapidly within the first 5 min from 7.0 to 6.2, which is not optimal for ebselen's GPx-like activity.Meanwhile, since ebselen has shown promising activity in the treatment of stroke, it seems that GPx-like activity of ebselen in the brain may not occur.Thus, the enzymatic reduction of ebselen by TrxR might be the main contribution to its antioxidant property during ischemia. Unlike inorganic and aliphatic selenium compounds, ebselen does not liberate the selenium moiety, which remains within the ring structure. Subsequent metabolism involves methylation, glucuronidation and hydroxylation. Additionally, ebselen could also inhibit enzymes such as lipoxygenases, nitric oxide synthases, nitrogen oxides, protein kinase C and H1/K1-ATPase. Besides the relationship with redox systems, another neuroprotective mechanism of ebselen is involved in controlling the expression of gaminobutyric acid shunt enzymes to supply the tricarboxylic acid cycle, and significantly inhibiting acetylcholinesterase activity,demonstrating its engagement in the metabolic system.
関連反応
7 件
化合物ノート
読み込み中…