(5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

• ChemBase编号: 285
• 分子式: C17H17ClN6O3
• 平均质量: 388.80828
• 单一同位素质量: 388.10506611
• SMILES: Clc1ccc(N2[C@@H](OC(=O)N3CCN(CC3)C)c3nccnc3C2=O)nc1
• Canonical SMILES: CN1CCN(CC1)C(=O)O[C@H]1c2nccnc2C(=O)N1c1ccc(cn1)Cl
• InChI: InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3/t16-/m0/s1
• InChIKey: GBBSUAFBMRNDJC-INIZCTEOSA-N

名称和登记号

名称

• IUPAC标准名: (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
• IUPAC传统名: lunesta; eszopiclone
• 商标名: Estorra; Lunesta
• 别名: Lunesta; (S)-Zopiclone; [(9S)-8-(5-Chloropyridin-2-yl)-7-oxo-2,5,8-triazabicyclo[4.3.0]nona-1,3,5-trien-9-yl]4-methylpiperazine-1-carboxylate; Esopiclone; Eszopiclone; (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

登记号

• CAS号: 138729-47-2
• MDL号: MFCD03700720
• PubChem SID: 46505809; 160963748
• PubChem CID: 969472

理论计算性质

JChem

• Acid pKa: 13.038308
• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): -0.59504867
• LogD (pH = 7.4): 0.6902288
• Log P: 0.80654305
• 摩尔折射率: 95.8855 cm^3
• 极化性: 37.123627 Å^3
• 极化表面积: 91.76 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.97
• LOG S: -2.64
• 溶解度: 8.85e-01 g/l

分子性质

理化性质

• 溶解度: Acetone; Chloroform; Ethanol; Phosphate Buffer (pH 3.2); very slightly soluble
• 外观: White To Pale Yellow Solid
• 熔点: 202-204°C
• 疏水性(logP): 0.8; 1.253

安全信息

• 保存条件: -20°C Freezer

产品相关信息

• 纯度: 95%

详细说明

DrugBank - DB00402

• Drug Groups: approved
• Description: Eszopiclone, marketed by Sepracor under the brand-name Lunesta, is a nonbenzodiazepine hypnotic agent (viz., a sedative) used as a treatment for insomnia. Eszopiclone is the active stereoisomer of zopiclone, and belongs to the class of drugs known as cyclopyrrones.; ; Its main selling point is that it is approved by the U.S. Food and Drug Administration for long-term use, unlike almost all other hypnotic sedatives, which are approved only for the relief of short-term (6-8 weeks) insomnia.
• Indication: For the treatment of insomnia
• Pharmacology: Eszopiclone is a nonbenzodiazepine hypnotic, pyrrolopyrazine derivative of the cyclopyrrolone class and is indicated for the short-term treatment of insomnia. While Eszopiclone is a hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties, it interacts with the gamma-aminobutyric acid-benzodiazepine (GABA_BZ) receptor complex. Subunit modulation of the GABA_BZ receptor chloride channel macromolecular complex is hypothesized to be responsible for some of the pharmacological properties of benzodiazepines, which include sedative, anxiolytic, muscle relaxant, and anticonvulsive effects in animal models. Eszopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.
• Toxicity: Side effects include viral infection, dry mouth, dizziness, hallucinations, infection, rash, and unpleasant taste, with this relationship clearest for unpleasant taste depending on doses.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following oral administration, eszopiclone is extensively metabolized by oxidation and demethylation.
• Absorption: Rapidly absorbed following oral administration
• Half Life: 6 hours
• Protein Binding: 52-59%
• Elimination: Up to 75% of an oral dose of racemic zopiclone is excreted in the urine, primarily as metabolites.
• External Links: Wikipedia; RxList

Toronto Research Chemicals - E889150

Eszopiclone is the active stereoizomer of Zopiclone and belongs to the class of drug known as cyclopyrrones. It is a nonbenzodiazepine hypnotic agent used as a treatment for insomnia.This is a controlled substance (depressant) in the US but not in Canada.

参考文献

• Gottesmann, C., et al.: Eur. J. Neurosci., 10, 409 (1998)
• Yoshimoto, M., et al.: Eur. Neuropsychopharmacol., 9, 29 (1998)