13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene

• ChemBase编号: 291
• 分子式: C18H18ClN3O
• 平均质量: 327.80802
• 单一同位素质量: 327.11383989
• SMILES: Clc1cc2C(=Nc3c(Oc2cc1)cccc3)N1CCN(CC1)C
• Canonical SMILES: CN1CCN(CC1)C1=Nc2ccccc2Oc2c1cc(Cl)cc2
• InChI: InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3
• InChIKey: XJGVXQDUIWGIRW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene; 13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene
• IUPAC传统名: loxapine
• 商标名: Cloxazepine; Dibenzacepin; Dibenzoazepine; Hydrofluoride 3170; Lossapina [Dcit]; Loxapac; Loxapin; Loxapina [INN-Spanish]; Loxapine [Usan:Ban:Inn]; Loxapinum [INN-Latin]; Loxepine; Loxitane C; Loxitane Im; Oxilapine
• 别名: Loxapine

登记号

• CAS号: 1977-10-2
• PubChem SID: 160963754; 46505047
• PubChem CID: 3964
• CHEBI ID: 50841
• ATC码: N05AH01
• CHEMBL: 831
• Chemspider ID: 3827
• DrugBank ID: DB00408
• IUPHAR配体索引: 205
• KEGG ID: D02340
• 美国药典/FDA物质标识码: LER583670J
• 维基百科标题: Loxapine
• Medline Plus: a682311

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.7827977
• LogD (pH = 7.4): 3.25769
• Log P: 3.4606025
• 摩尔折射率: 95.1111 cm^3
• 极化性: 35.46127 Å^3
• 极化表面积: 28.07 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.18
• LOG S: -3.5
• 溶解度: 1.03e-01 g/l

分子性质

理化性质

• 熔点: 109-110 °C (228.2-230°F)
• 疏水性(logP): 3.6

药理学性质

• 排泄: Majority are excreted within 24 hours. Main route through urine(conjugated metabolites); Small amounts through the faeces(unconjugated metabolites)
• 半衰期: Oral-4 hours
• 代谢: Gastrointestinal, peak concn. occur between 1-2 hours.

详细说明

DrugBank - DB00408

• Drug Groups: approved
• Description: An antipsychotic agent used in schizophrenia. [PubChem]
• Indication: For the management of the manifestations of psychotic disorders such as schizophrenia
• Pharmacology: Loxapine, a dibenzoxazepine compound, represents a subclass of tricyclic antipsychotic agents, chemically distinct from the thioxanthenes, butyrophenones, and phenothiazines. Pharmacologically, Loxapine is a tranquilizer for which the exact mode of action has not been established, however, it is believed that by antagonising dopamine and serotonin receptors, there is a marked cortical inhibition which can manifest as tranquilization and suppression of aggression.
• Toxicity: LD₅₀=65 mg/kg (Orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Systemic bioavailability of the parent drug was only about one third that after an equivalent intramuscular dose (25 mg base) in male volunteers
• Half Life: Oral-4 hours
• Elimination: Metabolites are excreted in the urine in the form of conjugates and in the feces unconjugated.
• References: Glazer WM: Does loxapine have "atypical" properties? Clinical evidence. J Clin Psychiatry. 1999;60 Suppl 10:42-6. [Pubmed] ; Cheung SW, Tang SW, Remington G: Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):213-21. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Glazer WM: Does loxapine have "atypical" properties? Clinical evidence. J Clin Psychiatry. 1999;60 Suppl 10:42-6. Pubmed
• Cheung SW, Tang SW, Remington G: Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):213-21. Pubmed