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Зопиклон , Zopiclone, زوبيكلون , 佐匹克隆

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Zopiclone structure.svg

ZOPICLONE

зопиклон
زوبيكلون
佐匹克隆
(±)-Zopiclone
1-Piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester
256-138-9 [EINECS]
43200-80-2 [RN]

Structural formula

UV- Spectrum

Conditions : Concentration – 1 mg / 100 ml
The solvent designation schedule methanol 

water 

0.1М HCl

0.1M NaOH

maximum absorption There 

decay

303 nm 304 nm 277 nm 

237 nm

362 364 199

390

e 10500 10500 5800

11300

IR – spectrum

Wavelength (μm)
Wave number (cm -1 )

MASS spectrum

Range
10 largest peaks:
Peak 42 56 99 112 139 143 217 245 246 247
Value 155 231 280 283 209 999 279 719 156 250

References

  • UV and IR Spectra. H.-W. Dibbern, R.M. Muller, E. Wirbitzki, 2002 ECV

  • NIST/EPA/NIH Mass Spectral Library 2008

  • Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman. Academic Press, 2000.

  • Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Brief background information

Salt ATC formula MM CASE
N05CF01 17 H 17 ClN 6 O 3 388.82 g / mol 43200-80-2

Application

  • sedative

  • hypnotic

Classes substance

  • chlorine compounds

    • oxo

      • Esters of 1-piperazinecarboxylate

        • pyridines

          • Pirrolo [3,4-b] piraziny

Synthesis Way

Синтез a)

Trade names

country Tradename Manufacturer
Germany Optydorm DOLORGIET
Somnosan Hormos
Ksimovan Sanofi-Aventis
Zop HEXAL
Zopi-cigar Actavis
various generic drugs
France imovane SanofiAventis
Noktireks Sanofi-Synthélabo
United Kingdom Snowman SanofiAventis
Italy imovane SanofiAventis
tion THERE
Japan Amoʙan Sanofi-Aventis; Chugai; Mitsubishi
Ukraine imovane Sanofi Winthrop Indastria, France
various generic drugs

Formulations

  • coated tablets 7.5 mg;

  • Tablets 7.5 mg, 10 mg

References

  • DOS 2 300 491 (Rhône-Poulenc; appl. 5.1.1973; F-prior. 7.1.1972, 9.9.1972).

  • US 3 862 149 (Rhône-Poulenc; 21.1.1975; F-prior. 7.1.1972, 9.9.1972).

Two major zopiclone metabolites.

Two major zopiclone metabolites.

CAS Registry No.: 43200-80-2
Molecular Formula: C17H17ClN6O3 Molecular Weight: 388.8
ChemicalStructure
Compound Name:
zopiclone

1-piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl ester

4-methyl-1-piperazinecarboxylic acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)-pyrazin-5-yl ester

4-methyl-1-piperazinecarboxylic acid-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)-pyrazin-5-yl ester

6-(5-chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1-piperazinecarboxylate

6-(5-chloro-pyridin-2-yl)-5((4-methyl-1-piperazinyl)carbonyloxy)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

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

amoban (R)

imovane

Zopiclone (Imovance), 4-methyl-1-piperzinecarboxylic acid 6-(5-chloro-2- pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester (Figure 1) is one of the non benzodiazepine sedative-hypnotics of the cyclopyrrolone class, sold by Rhone-Poulene Company in France since 1987. Although structurally unrelated to benzodiazepines, its pharmacological profile is similar, exhibiting sedative-hypnotic, anxiolytic, myorelaxant, and anticonvulsant activity.[1] Other than the first generation barbiturates and the second-generation benzodiazepines, zopiclone, which is widely used in Europe as well as other regions worldwide,[2,3] as a representative of the third generation sedative-hypnotic drugs, has been shown to be free from residual effects on performance and psychological function the day after intake and from the risks of accumulation because of its short elimination half-life (3.5 to 6.5 hours).[3,4] It is indicated for the short term treatment of insomnia, transient, situational or chronic insomnia, and insomnia secondary to psychiatric disturbances.[3]

REFERENCES 1. Mann, K.; Bauer, H.; Hiemke, C.; Ro¨schke, J.; Wetzel, H.; Benkert, O. Acute, subchronic and discontinuation effects of zopiclone on sleep EEG and nocturnal melatonin secretion. Eur. Neuropsychopharm. 1996, 6 (3), 163– 168. Structure Elucidation of Sedative-Hypnotic Zopiclone 359 Downloaded by [Dalhousie University] at 22:10 19 December 2012

2. Le´ger, D.; Janus, C.; Pellois, A.; Quera-Salva, M.A.; Dreyfus, J.P. Sleep, morning alertness and quality of life in subjects treated with zopiclone and in good sleepers. study comparing 167 patients and 381 good sleepers. Eur. Psychiat. 1995, 10 (973) Suppl. 3, 99s – 102s.

3. Piperaki, S.; Parissi-Poulou, M. Enantiomeric separation of zopiclone, its metabolites and products of degradation on a b-cyclodextrin bonded phase. J. Chromatogr. A 1996, 729 (1 – 2), 19 – 28

Spectral Data Analyses and Structure Elucidation of Sedative‐Hypnotic Zopiclone

Pages 349-360 | Received 10 Sep 2006, Accepted 18 Oct 2006, Published online: 13 Oct 2010

Zopiclone
Zopiclone structure.svg
Zopiclone ball-and-stick.png
Systematic (IUPAC) name

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

Clinical data
Trade names Imovane, Zimovane
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • AU: C
  • US: C (Risk not ruled out)
Routes of
administration
Oral tablets, 3.75 mg (UK), 5 or 7.5 mg
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: Class C (POM)
  • US: Schedule IV
Pharmacokinetic data
Bioavailability 75-80%[1]
Protein binding 52–59%
Metabolism Hepatic through CYP3A4and CYP2E1
Biological half-life ~5 hours (3.5–6.5 hours)

~7–9 hours for over 65

Excretion Urine (80%)
Identifiers
CAS Number 43200-80-2 Yes
ATC code N05CF01 (WHO)
PubChem CID 5735
IUPHAR/BPS 7430
DrugBank DB01198 Yes
ChemSpider 5533 Yes
UNII 03A5ORL08Q Yes
KEGG D01372 Yes
ChEBI CHEBI:32315 Yes
ChEMBL CHEMBL135400 Yes
PDB ligand ID ZPC (PDBeRCSB PDB)
Chemical data
Formula C17H17ClN6O3
Molar mass 388.808 g/mol
3D model (Jmol) Interactive image

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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