基本情報
- CAS
106516-24-9- 標準SMILES
O=C1NCCN1CCN1CCC(c2cn(-c3ccc(F)cc3)c3ccc(Cl)cc23)CC1- InChIKey
GZKLJWGUPQBVJQ-UHFFFAOYSA-N- 分子式
- C24H26ClFN4O
- 平均分子量
- 440.9 g/mol
- 単同位体質量
- 440.17791735
概要
Sertindole is a phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group. It has a role as an alpha-adrenergic antagonist, a H1-receptor antagonist, a serotonergic antagonist and a second generation antipsychotic. It is an organochlorine compound, an organofluorine compound, a phenylindole, a heteroarylpiperidine and an imidazolidinone.
名称と識別子
- 優先名称
- Sertindole
- IUPAC
- 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one
- 現地名
- セルチンドール
- 英語名
- Sertindole
- 分子式
- C24H26ClFN4O
- 分子量
- 440.94
名称と別名
SERTINDOLE106516-24-9SerLectSerdolectSertindolSertindolumLu 23-174zerdolLu-23-1741-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-oneDTXSID60489671-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
名称をさらに表示
1-(4-フルオロフェニル)-5-クロロ-3-[1-[2-[(テトラヒドロ-2-オキソ-1H-イミダゾール)-1-イル]エチル]ピペリジン-4-イル]-1H-インドール1-[2-[4-[1-(4-フルオロフェニル)-5-クロロ-1H-インドール-3-イル]ピペリジノ]エチル]イミダゾリジン-2-オンセルチンドール1-(4-フルオロフェニル)-5-クロロ-3-[1-[2-(2-オキソ-1-イミダゾリジニル)エチル]-4-ピペリジニル]-1H-インドール1-[2-[4-[5-クロロ-1-(4-フルオロフェニル)-1H-インドール-3-イル]-1-ピペリジニル]エチル]-2-イミダゾリジノン1-(2-{4-[5-クロロ-1-(4-フルオロフェニル)-1H-インドール-3-イル]ピペリジン-1-イル}エチル)イミダゾリジン-2-オンS-1991SerdoleetSertindole>SUBSTANCE 5364890SERTINDOLE USP/EP/BP
GVV4Z879SP1-(2-(4-(5-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl)piperidin-1-yl)ethyl)imidazolidin-2-oneCHEBI:9122DTXCID30288931-(2-(4-(5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone1-[2-[4-[5-chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-one1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone1-(2-(4-(5-chloro-1-(4-fluorophenyl)-indol-3-yl)-1-piperidyl)ethyl)imidazolidin-2-one
物性
構造計算による物性
- XLogP
- 4.1
- 極性表面積
- 40.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 5
- 重原子数
- 31
- 形式電荷
- 0
- 複雑度
- 623
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antipsychotics
Pharmaceuticals -> Nervous system -> Antipsychotics
Solubility9.63e-03 g/L
Physical DescriptionSolid
Collision Cross Section215.9 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
物理化学的性質
- 融点
- 95 · 95-100°C
- 沸点
- 592.1 · 592.1±50.0 °C(Predicted)
- 比重(密度)
- 1.36 · 1.36
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 10 mg/mL · DMSO：>10mg/mL
- 外見
- 個体
- 酸解離定数(Pka)
- 14.53 · 14.53±0.20(Predicted)
- 色
- オフホワイト
- Merck
- 14 · 14,8466
- InChI
- InChI=1S/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)
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
Warning
H315 (95.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 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 CategoriesSkin Irrit. 2 (95.2%)
安全データ
- wgk
- 3
- rtecs
- NJ0621100
- hs_code
- 2933.99.6100
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
化学と産業
薬理情報
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Sertindole is an atypical antipsychotic at least as effective as haloperidol and risperidone in the treatment of neuroleptic-responsive schizophrenia. Sertindole improves negative symptoms, and is also effective for the treatment of neuroleptic-resistant schizophrenia. Sertindole is generally well tolerated and is associated with a low rate of extrapyramidal symptoms (EPS).
Mechanism of Action
Sertindole is an antipsychotic drug with affinity for dopamine D2, serotonin 5-HT2A and 5-HT2C, and alpha1-adrenoreceptors. Preclinical studies suggest that sertindole acts preferentially on limbic and cortical dopaminergic neurons and clinical trials have confirmed that sertindole is effective at a low dopamine D2 occupancy level.
Biological Half-Life3 days
Metabolism/Metabolites
Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.
Sertindole has known human metabolites that include 1-[2-[4-[5-Chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]-4-hydroxyimidazolidin-2-one and 5-Chloro-1-(4-fluorophenyl)-3-(piperidin-4-yl)-1H-indole.
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Absorption, Distribution and ExcretionOrally available.
関連反応
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