CAS 43200-80-2|Zopiclona [INN-Spanish]|Zopiclonum [INN-Latin]|Zopiclone [Ban:Inn:Jan]|Ran-zopiclone|Ximovan|6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-ca...

General Information

Structure

Molecular Formula

C₁₇H₁₇ClN₆O₃

Molecular Mass

388.80828

Exact Mass

388.10506611

Charge

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

Canonic Smiles

CN1CCN(CC1)C(=O)OC1c2nccnc2C(=O)N1c1ccc(cn1)Cl

Isomeric Smiles

Clc1ccc(N2C(OC(=O)N3CCN(CC3)C)c3nccnc3C2=O)nc1

Calculated Properties

JChem

Acid pKa

13.038308

H Acceptors

H Donor

LogD (pH = 5.5)

-0.59504867

LogD (pH = 7.4)

0.6902288

Log P

0.80654305

Molar Refractivity

95.8855

Polarizability

37.123627

Polar Surface Area

91.76

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.97

LOG S

-2.64

Solubility (Water)

8.85e-01 g/l

Data Source

Names and Identifiers

Synonyms

Zopiclona [INN-Spanish]Zopiclonum [INN-Latin]Zopiclone [Ban:Inn:Jan]Zopiclone(+-)-zopiclone4-Methyl-1-piperazinecarboxylic acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl esterImovaneZopicloneZimovaneLunesta 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylateLimovan4-Methyl-1-piperazine-carboxylic Acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl EsterRP-27267SopivanAmobanXimovanImovance

Brand Name

Ran-zopicloneXimovanAmobanNu-ZopicloneSopivanImovaneRhovaneZimovaneAmovaneImovanceNovo-zopicloneImovane, Zimovane

IUPAC name

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

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

CAS Number

43200-80-2

MDL Number

MFCD00133931

PubChem SID

2427814846505233160964531

EC Number

PubChem CID

CHEBI ID

KEGG ID

Wikipedia Title

CHEMBL

Unique Ingredient Identifier

DrugBank ID

ATC CODE

Chemspider ID

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1446

Related research area: Neurological Disease

DrugBank

DB01198

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 (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. 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]

Wikipedia

Zopiclone

Sigma Aldrich

Z4900

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.

TRC

Z700500

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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)

• Fernandez, C. et al., Clin. Pharmacokinet., 1995, 29, 431, (rev, pharmacokinet)

• Borea, P.A. et al., Mol. Pharmacol., 1987, 31, 334, (struct)

• Goa, K.L. et al., Drugs, 1986, 32, 48, (rev, pharmacol)

• Jeanmart, C. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1978, 287, 377, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 622

• Schulz, M., Pharm. Ztg., 1991, 136, 26; 30, (rev)

• Brun, J.P., Pharmacol., Biochem. Behav., 1988, 29, 831, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ZUA450

• Noble, S. et al., Drugs, 1998, 55, 277-302, (rev)

• Bertolasi, V. et al., J.C.S. Perkin 2, 1990, 283, (cryst struct)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

Ran-zopicloneXimovanAmobanNu-ZopicloneSopivanImovaneRhovaneZimovaneAmovaneImovanceNovo-zopicloneImovane, Zimovane

IUPAC name

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

IUPAC Traditional name

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

Registration numbers

CAS Number

43200-80-2

MDL Number

MFCD00133931

PubChem SID

2427814846505233160964531

EC Number

PubChem CID

CHEBI ID

KEGG ID

Wikipedia Title

CHEMBL

Unique Ingredient Identifier

DrugBank ID

ATC CODE

Chemspider ID

Molecule Details

S1446

Related research area: Neurological Disease

DrugBank

DB01198

Drug Groups

approved

Description

Indication

For the short-term treatment of insomnia.

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

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

• 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]

Z4900

Z700500

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.

References

PubChem Literature

From Data Sources

• 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

• 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)

• Fernandez, C. et al., Clin. Pharmacokinet., 1995, 29, 431, (rev, pharmacokinet)

• Borea, P.A. et al., Mol. Pharmacol., 1987, 31, 334, (struct)

• Goa, K.L. et al., Drugs, 1986, 32, 48, (rev, pharmacol)

• Jeanmart, C. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1978, 287, 377, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 622

• Schulz, M., Pharm. Ztg., 1991, 136, 26; 30, (rev)

• Brun, J.P., Pharmacol., Biochem. Behav., 1988, 29, 831, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ZUA450

• Noble, S. et al., Drugs, 1998, 55, 277-302, (rev)

• Bertolasi, V. et al., J.C.S. Perkin 2, 1990, 283, (cryst struct)

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:1068