1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one

• ChemBase编号: 4414
• 分子式: C24H26ClFN4O
• 平均质量: 440.9408432
• 单一同位素质量: 440.17791737
• SMILES: Clc1cc2c(C3CCN(CC3)CCN3CCNC3=O)cn(c2cc1)c1ccc(F)cc1
• Canonical SMILES: Clc1ccc2c(c1)c(cn2c1ccc(cc1)F)C1CCN(CC1)CCN1CCNC1=O
• 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)
• InChIKey: GZKLJWGUPQBVJQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(2-{4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]piperidin-1-yl}ethyl)imidazolidin-2-one
• IUPAC传统名: sertindole
• 商标名: Serdolect; Serlect
• 别名: 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone; Sertindole; Sertindol [inn-spanish]; Sertindolum [inn-latin]; Sertindole; Serdolect; Zerdol

登记号

• CAS号: 106516-24-9
• MDL号: MFCD00867749
• PubChem SID: 46504717; 160967846
• PubChem CID: 60149

理论计算性质

JChem

• LogD (pH = 7.4): 2.5622704
• Log P: 3.7738
• 摩尔折射率: 131.7697 cm^3
• 极化性: 48.06371 Å^3
• 极化表面积: 40.51 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true
• Acid pKa: 14.3581505
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.76146895

ALOGPS 2.1

• Log P: 4.29
• LOG S: -4.66
• 溶解度: 9.63e-03 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL; H2O: <2 mg/mL; Methanol
• 外观: off-white solid; Off-White to Pale Yellow Solid
• 熔点: 150-152°C

安全信息

• 保存条件: Refrigerator
• RTECS编号: NJ0621100
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335-H413
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.5% (HPLC)
• Empirical Formula (Hill Notation): C24H26ClFN4O

详细说明

DrugBank - DB06144

• Drug Groups: approved; withdrawn
• Description: Sertindole, a neuroleptic, is one of the newer antipsychotic medications available. Serdolect is developed by the Danish pharmaceutical company H. Lundbeck. Like the other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia. It is classified chemically as a phenylindole derivative. It was first marketed in 1996 in several European countries before being withdrawn two years later because of numerous cardiac adverse effects. It has once again been approved and should soon be available on the French and Australian market.
• Indication: Used in the treatment of schizophrenia.
• Pharmacology: 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).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Sertindole is metabolized by cytochrome P450 isoenzymes CYP 2D6 and CYP 3A4.
• Absorption: Orally available.
• Half Life: 3 days
• References: Kane JM, Tamminga CA: Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. Expert Opin Investig Drugs. 1997 Nov;6(11):1729-41. [Pubmed] ; Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. [Pubmed] ; Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. [Pubmed] ; Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. [Pubmed] ; Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. [Pubmed] ; Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. [Pubmed] ; Hertel P: Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. Synapse. 2006 Dec 1;60(7):543-52. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - S8072

Biochem/physiol Actions
Sertindole is a 5-HT2 serotonin and D2 dopamine receptor antagonist and antipsychotic.

Toronto Research Chemicals - S279500

Antipsychotic used in the treatment of schizophrenia.

参考文献

• Lindstrom E, Levander S: Sertindole: efficacy and safety in schizophrenia. Expert Opin Pharmacother. 2006 Sep;7(13):1825-34. Pubmed
• Hertel P: Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. Synapse. 2006 Dec 1;60(7):543-52. Pubmed
• Kane JM, Tamminga CA: Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. Expert Opin Investig Drugs. 1997 Nov;6(11):1729-41. Pubmed
• Lewis R, Bagnall AM, Leitner M: Sertindole for schizophrenia. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD001715. Pubmed
• Perquin LN: Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects. Int Clin Psychopharmacol. 2005 Nov;20(6):335-8. Pubmed
• Murdoch D, Keating GM: Sertindole : a review of its use in schizophrenia. CNS Drugs. 2006;20(3):233-55. Pubmed
• Sertindole: new drug. Another "atypical" neuroleptic; QT prolongation. Prescrire Int. 2007 Apr;16(88):59-62. Pubmed
• Nourian, Z., et al.: Eur. J. Pharmacol., 596, 32 (2008)
• Karczewski, J., et al.: Biochem. Pharmacol., 77, 1602 (2008)
• Isoherranen, N., et al.: Chem. Res. Toxicol., 22, 294 (2008)
• Goetghebeur, P., et al.: Psychopharmacol., 202, 287 (2008)