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43200-80-2 分子结构
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6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

ChemBase编号:1068
分子式:C17H17ClN6O3
平均质量:388.80828
单一同位素质量:388.10506611
SMILES和InChIs

SMILES:
Clc1ccc(N2C(OC(=O)N3CCN(CC3)C)c3nccnc3C2=O)nc1
Canonical SMILES:
CN1CCN(CC1)C(=O)OC1c2nccnc2C(=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
InChIKey:
GBBSUAFBMRNDJC-UHFFFAOYSA-N

引用这个纪录

CBID:1068 http://www.chembase.cn/molecule-1068.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
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
zopiclone
6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
商标名
Amoban
Amovane
Imovance
Imovane
Sopivan
Zimovane
Nu-Zopiclone
Novo-zopiclone
Ran-zopiclone
Rhovane
Ximovan
Imovane, Zimovane
别名
Zopiclona [INN-Spanish]
Zopiclone [Ban:Inn:Jan]
Zopiclonum [INN-Latin]
(+-)-zopiclone
Zopiclone
Imovane
Zimovane
Lunesta
6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
4-Methyl-1-piperazinecarboxylic acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester
Zopiclone
4-Methyl-1-piperazine-carboxylic Acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl Ester
RP-27267
Amoban
Limovan
Sopivan
Ximovan
Imovance
CAS号
43200-80-2
EC号
256-138-9
MDL号
MFCD00133931
PubChem SID
24278148
46505233
160964531
PubChem CID
5735
CHEBI ID
32315
ATC码
N05CF01
CHEMBL
135400
Chemspider ID
5533
DrugBank ID
DB01198
KEGG ID
D01372
美国药典/FDA物质标识码
03A5ORL08Q
维基百科标题
Zopiclone

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 13.038308  质子受体
质子供体 LogD (pH = 5.5) -0.59504867 
LogD (pH = 7.4) 0.6902288  Log P 0.80654305 
摩尔折射率 95.8855 cm3 极化性 37.123627 Å3
极化表面积 91.76 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 0.97  LOG S -2.64 
溶解度 8.85e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
0.151 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] expand 查看数据来源
Acetone expand 查看数据来源
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
DMSO: soluble2 mg/mL expand 查看数据来源
H2O: insoluble expand 查看数据来源
外观
Off-White Solid expand 查看数据来源
熔点
173-175°C (dec.) expand 查看数据来源
疏水性(logP)
0.8 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
RTECS编号
TL1425000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
20/21/22-36/37/38-62 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302-H312-H315-H319-H332-H335-H361 expand 查看数据来源
GHS警示性声明
P261-P280-P305 + P351 + P338 expand 查看数据来源
个人保护装置
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
毒品管制信息
USDEA Schedule IV; psychotrope; regulated under CDSA - not available from Sigma-Aldrich Canada expand 查看数据来源
给药途径
Oral tablets, 3.75mg (UK), 5 or 7.5 mg expand 查看数据来源
生物利用度
52-59% bound to plasma protein expand 查看数据来源
排泄
Urine expand 查看数据来源
半衰期
~6 hours
~9 hours for over 65
expand 查看数据来源
代谢
Various cytochrome P450 liver enzymes expand 查看数据来源
法定药品分级
POM (UK) expand 查看数据来源
Schedule IV (US) expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源
相关基因信息
human ... BZRAP1(9256) expand 查看数据来源
生物活性机理
The mechanism of action of zopiclone is similar to benzodiazepines, with similar effects on locomotor activity and on dopamine and serotonin turnover expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Anticonvulsant expand 查看数据来源
Psychosedative expand 查看数据来源
Sedative expand 查看数据来源
Tranquilizer expand 查看数据来源

详细说明

详细说明

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank Selleck Chemicals Selleck Chemicals
Sigma Aldrich -  Z4900 external link
Biochem/physiol Actions
Benzodiazepine receptor agonist
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. Z4900.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals -  Z700500 external link
Cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists. This is a controlled substance (depressant) in the US but not in Canada. Sedative, hypnotic.
DrugBank -  DB01198 external link
Item Information
Drug Groups approved
Description Zopiclone is a novel hypnotic agent used in the treatment of insomnia. Its mechanism of action is based on modulating benzodiazepine receptors. In addition to zopiclone's benzodiazepine pharmacological properties it also has some barbiturate like properties.
Indication For the short-term treatment of insomnia.
Pharmacology Zopiclone is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class and is indicated for the short-term treatment of insomnia. While Zopiclone 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 (GABABZ) receptor complex. Subunit modulation of the GABABZ 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. Zopiclone binds selectively to the brain alpha subunit of the GABA A omega-1 receptor.
Toxicity Rare individual instances of fatal outcomes following overdose with racemic zopiclone have been reported in European postmarketing reports, most often associated with overdose with other CNS-depressant agent. Signs and symptoms of overdose effects of CNS depressants can be expected to present as exaggerations of the pharmacological effects noted in preclinical testing.
Affected Organisms
Humans and other mammals
Biotransformation Extensively metabolized in the liver via decarboxylation (major pathway), demethylation, and side chain oxidation. Metabolites include an N-oxide derivative (weakly active; approximately 12% of a dose) and an N-desmethyl metabolite (inactive; approximately 16%). Approximately 50% of a dose is converted to other inactive metabolites via decarboxylation. Hepatic microsomal enzymes are apparently not involved in zopiclone clearance.
Absorption Rapidly absorbed following oral administration.
Half Life Elimination half life is approximately 5 hours (range 3.8 to 6.5 hours) and is prolonged to 11.9 hours in patients with hepatic insufficiency.
Protein Binding Approximately 45%
References
Liu HJ, Sato K, Shih HC, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats. Int J Clin Pharmacol Ther Toxicol. 1985 Mar;23(3):121-8. [Pubmed]
Sato K, Hong YL, Yang MS, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition. Int J Clin Pharmacol Ther Toxicol. 1985 Apr;23(4):204-10. [Pubmed]
Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22. [Pubmed]
Blanchard JC, Julou L: Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. J Neurochem. 1983 Mar;40(3):601-7. [Pubmed]
Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58. [Pubmed]
External Links
Wikipedia
Drugs.com
Selleck Chemicals -  S1446 external link
Related research area: Neurological Disease

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Liu HJ, Sato K, Shih HC, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats. Int J Clin Pharmacol Ther Toxicol. 1985 Mar;23(3):121-8. Pubmed
  • Sato K, Hong YL, Yang MS, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition. Int J Clin Pharmacol Ther Toxicol. 1985 Apr;23(4):204-10. Pubmed
  • Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22. Pubmed
  • Blanchard JC, Julou L: Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. J Neurochem. 1983 Mar;40(3):601-7. Pubmed
  • Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58. Pubmed
  • Jeanmart, C. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1978, 287, 377, (synth, pharmacol)
  • Goa, K.L. et al., Drugs, 1986, 32, 48, (rev, pharmacol)
  • Borea, P.A. et al., Mol. Pharmacol., 1987, 31, 334, (struct)
  • Brun, J.P., Pharmacol., Biochem. Behav., 1988, 29, 831, (rev)
  • Bertolasi, V. et al., J.C.S. Perkin 2, 1990, 283, (cryst struct)
  • Schulz, M., Pharm. Ztg., 1991, 136, 26; 30, (rev)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 622
  • Fernandez, C. et al., Clin. Pharmacokinet., 1995, 29, 431, (rev, pharmacokinet)
  • http://en.wikipedia.org/wiki/Zopiclone
  • Noble, S., et al.: Drugs, 55, 277 (1998)
  • Musch, B., et al.: Int. J. Clin. Psychopharmacol., 5, 147 (1998)
  • Noble, S. et al., Drugs, 1998, 55, 277-302, (rev)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ZUA450
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专利

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