7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one

• ChemBase编号: 1107
• 分子式: C23H27Cl2N3O2
• 平均质量: 448.38538
• 单一同位素质量: 447.14803248
• SMILES: Clc1c(N2CCN(CC2)CCCCOc2cc3NC(=O)CCc3cc2)cccc1Cl
• Canonical SMILES: O=C1CCc2c(N1)cc(cc2)OCCCCN1CCN(CC1)c1cccc(c1Cl)Cl
• InChI: InChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)
• InChIKey: CEUORZQYGODEFX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
• IUPAC传统名: aripiprazole; 7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
• 商标名: Abilify; Abilitat
• 别名: OPC-14597; OPC 31; aripiprazole; Aripiprazole; 7-[4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone; 7-[4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydrocarbostyril; Abilify; Abilitat; OPC 14597; 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one; Aripiprazole (Abilify); Aripiprazole; 7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one

登记号

• CAS号: 129722-12-9
• MDL号: MFCD00892072
• PubChem SID: 46505745; 160964570
• PubChem CID: 60795

理论计算性质

JChem

• Acid pKa: 13.512109
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 2.9477053
• LogD (pH = 7.4): 4.5687175
• Log P: 4.9012437
• 摩尔折射率: 124.3364 cm^3
• 极化性: 47.03606 Å^3
• 极化表面积: 44.81 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 5.21
• LOG S: -4.76
• 溶解度: 7.77e-03 g/l

分子性质

理化性质

• 溶解度: 1mg/ml Methanol; 2mg/ml DMSO; 2mg/ml Ethanol
• 外观: Off-White Solid
• 熔点: 138-140°C
• 疏水性(logP): 4.5; 5.312

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 作用靶点: 5-HT Receptor
• 生物活性机理: Shows presynaptic dopamine autoreceptor agonist activity and postsynaptic dopamine D2-receptor antagonist activity

产品相关信息

• 纯度: 95%; 95+%
• 成盐信息: Free Base
• 应用领域: Antipsychotic agent

详细说明

DrugBank - DB01238

• Drug Groups: approved; investigational
• Description: Aripiprazole is an atypical antipsychotic medication used for the treatment of schizophrenia. It has also recently received FDA approval for the treatment of acute manic and mixed episodes associated with bipolar disorder. Aripiprazole appears to mediate its antipsychotic effects primarily by partial agonism at the D2 receptor. In addition to partial agonist activity at the D2 receptor, aripiprazole is also a partial agonist at the 5-HT1A receptor, and like the other atypical antipsychotics, aripiprazole displays an antagonist profile at the 5-HT2A receptor. Aripiprazole has moderate affinity for histamine and alpha adrenergic receptors, and no appreciable affinity for cholinergic muscarinic receptors.
• Indication: For the treatment of schizophrenia and related psychotic disorders.
• Pharmacology: Aripiprazole is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Aripiprazole is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT2), dopamine Type 2 (D2), 1 and 2 adrenergic, and H1 histaminergic receptors. Aripiprazole acts as an antagonist at other receptors, but with lower potency. Antagonism at receptors other than dopamine and 5HT2 with similar receptor affinities may explain some of the other therapeutic and side effects of Aripiprazole. Aripiprazole's antagonism of histamine H1 receptors may explain the somnolence observed with this drug. Aripiprazole's antagonism of adrenergic a1 receptors may explain the orthostatic hypotension observed with this drug.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 75-146 hours
• Protein Binding: >99%
• Elimination: Less than 1% of unchanged aripiprazole was excreted in the urine and approximately 18% of the oral dose was recovered unchanged in the feces.
• Distribution: * 4.9 L/kg
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - A771000

A selective dopamine D2-receptor antagonist with dopamine autoreceptor agonist activity. Antipsychotic.

参考文献

• Canive, J.M., et al.: Psychopharmacol. Bull., 34, 101 (1998)
• Oshiro, Y., et al.: J. Med. Chem., 41, 658 (1998)
• Eur. Pat., 1990, Otsuka, 367 141; CA, 113, 152468y, (synth, pharmacol)
• Kikuchi, T. et al., J. Pharmacol. Exp. Ther., 1995, 274, 329-336, (pharmacol)
• Semba, J. et al., Neuropharmacology, 1995, 34, 785-791, (pharmacol)
• Inoue, T. et al., J. Pharmacol. Exp. Ther., 1996, 277, 137-143, (pharmacol)
• Inoue, T. et al., Eur. J. Pharmacol., 1997, 321, 105-111, (pharmacol)
• Yamada, S. et al., J. Pharm. Pharmacol., 1997, 49, 206-208, (pharmacol)
• Morita, S. et al., Tetrahedron, 1998, 54, 4811-4818, (metab)