8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

• ChemBase编号: 373
• 分子式: C21H31N5O2
• 平均质量: 385.50314
• 单一同位素质量: 385.24777526
• SMILES: O=C1N(C(=O)CC2(CCCC2)C1)CCCCN1CCN(CC1)c1ncccn1
• Canonical SMILES: O=C1CC2(CCCC2)CC(=O)N1CCCCN1CCN(CC1)c1ncccn1
• InChI: InChI=1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2
• InChIKey: QWCRAEMEVRGPNT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione
• IUPAC传统名: buspirone
• 商标名: Ansial; Ansiced; Anxiron; Axoren; Bespar; Buspar; Buspimen; Buspinol; Buspisal; Censpar; Lucelan; Narol; Travin; Wellbutrin XL
• 别名: Buspirona [INN-Spanish]; Buspirone HCL; Buspironum [INN-Latin]; Buspirone; Buspirone; 8-(4-(4-(PyriMidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

登记号

• CAS号: 36505-84-7
• PubChem SID: 46508113; 160963836
• PubChem CID: 2477
• CHEBI ID: 3223
• ATC码: N05BE01
• CHEMBL: 49
• Chemspider ID: 2383
• DrugBank ID: DB00490
• IUPHAR配体索引: 36
• KEGG ID: D07593
• 美国药典/FDA物质标识码: TK65WKS8HL
• 维基百科标题: Buspirone
• Medline Plus: a688005

理论计算性质

JChem

• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): -0.32954732
• LogD (pH = 7.4): 1.351795
• Log P: 1.7767332
• 摩尔折射率: 108.8906 cm^3
• 极化性: 41.61726 Å^3
• 极化表面积: 69.64 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.95
• LOG S: -2.82
• 溶解度: 5.88e-01 g/l

分子性质

理化性质

• 溶解度: 21.4 mg/L
• 疏水性(logP): 2.3

药理学性质

• 给药途径: Oral
• 生物利用度: 5%
• 排泄: Urine (29-63%), Feces (18-38%)
• 半衰期: 2-3 hours
• 代谢: Hepatic
• 蛋白结合率: 95%
• 法定药品分级: Rx-only
• 妊娠期药物分类: B (US)

产品相关信息

• 纯度: 97%

详细说明

DrugBank - DB00490

• Drug Groups: approved; investigational
• Description: An anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam. [PubChem]
• Indication: For the management of anxiety disorders or the short-term relief of the symptoms of anxiety, and also as an augmention of SSRI-treatment against depression.
• Pharmacology: Buspirone is used in the treatment of generalized anxiety where it has advantages over other antianxiety drugs because it does not cause sedation (drowsiness) and does not cause tolerance or physical dependence. Buspirone differs from typical benzodiazepine anxiolytics in that it does not exert anticonvulsant or muscle relaxant effects. It also lacks the prominent sedative effect that is associated with more typical anxiolytics. in vitro preclinical studies have shown that buspirone has a high affinity for serotonin (5-HT_1A) receptors. Buspirone has no significant affinity for benzodiazepine receptors and does not affect GABA binding in vitro or in vivo when tested in preclinical models. Buspirone has moderate affinity for brain D2-dopamine receptors. Some studies do suggest that buspirone may have indirect effects on other neurotransmitter systems.
• Toxicity: Oral, rat LD₅₀ = 136 mg/kg. Symptoms of overdose include dizziness, drowsiness, nausea or vomiting, severe stomach upset, and unusually small pupils.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized hepatically, primarily by oxidation by cytochrome P450 3A4 producing several hydroxylated derivatives and a pharmacologically active metabolite, 1-pyrimidinylpiperazine (1-PP)
• Absorption: Rapidly absorbed in man. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism.
• Half Life: 2-3 hours (although the action of a single dose is much longer than the short halflife indicates).
• Protein Binding: 95% (approximately 70% bound to albumin, 30% bound to alpha 1 -acid glycoprotein)
• Elimination: In a single-dose study using 14C-labeled buspirone, 29% to 63% of the dose was excreted in the urine within 24 hours, primarily as metabolites; fecal excretion accounted for 18% to 38% of the dose.
• External Links: Wikipedia; RxList; Drugs.com