Eszopiclone

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Description References

Product Name: Eszopiclone
CAS No.: 138729-47-2
Chemical Name: Eszopiclone
Synonyms: Lunesta;ESOPICLONE;ESZOPICLONE;Eszppiclone;Dexzopiclone;Zopiclone (S)-;ESZOPICLONE CIV;ESZOPICLONE 99%;(S)-(+)-ZOPICLONE;Eszopiclone USP/EP/BP
CBNumber: CB1468825
Molecular Formula: C17H17ClN6O3
Formula Weight: 388.81
MOL File: 138729-47-2.mol

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Eszopiclone Property

Melting point:: 202-204°C
alpha: D20 +135 ±3° (c = 1.0 in acetone)
Boiling point:: 580.7±50.0 °C(Predicted)
Density: 1.54±0.1 g/cm3(Predicted)
storage temp.: -20°C Freezer
solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
form: Solid
pka: 6.70±0.10(Predicted)
color: White to Light Beige
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
SMILES: N1(C(O[C@H]2C3=NC=CN=C3C(=O)N2C2=NC=C(Cl)C=C2)=O)CCN(C)CC1
CAS DataBase Reference: 138729-47-2(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38-62
Safety Statements: 26-36
HS Code: 2933790002
Hazardous Substances Data: 138729-47-2(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Medical Isotopes, Inc.

Product number: 70052
Product name: Eszopiclone
Packaging: 10mg
Price: $625
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb146149
Product name: Eszopiclone
Purity: >98%
Packaging: 100mg
Price: $690.2
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0024379
Product name: ESZOPICLONE
Purity: 95.00%
Packaging: 1G
Price: $852.55
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb146149
Product name: Eszopiclone
Purity: >98%
Packaging: 250mg
Price: $912.9
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0024379
Product name: ESZOPICLONE
Purity: 95.00%
Packaging: 2.5G
Price: $1227.82
Updated: 2021/12/16

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Eszopiclone Chemical Properties,Usage,Production

Description

Approved by the FDA in December 2004, Eszopiclone is a non-benzodiazepine drug with hypnotic and sedative activity which is effective for the treatment of insomnia characterized by difficulty falling asleep, difficulty maintaining sleep or awakening frequently during the night, waking up too early, an inability to fall back to sleep and awakening in the morning not feeling refreshed. Eszopiclone belongs to cyclopyrrolone and dextrorotatory stereoisomer of zopiclone, which was the first non-benzodiazepine approved for insomnia in over 20 years. However, Eszopiclone is a controlled pharmaceuticals. Long-term intake of this substance or any other sedative drug probably induces drug dependence. Patients may experience withdrawal symptoms if the drug is stopped abruptly.

References

https://en.wikipedia.org/wiki/Eszopiclone
http://www.medicinenet.com/eszopiclone/article.htm
https://pubchem.ncbi.nlm.nih.gov/compound/969472#section=Top

Description

Eszopiclone is a non-benzodiazepine hypnotic agent indicated for the treatment of insomnia to induce sleep and for sleep maintenance. It has similar pharmacokinetic and pharmacodynamic parameters as the previously marketed non-benzodiazepine hypnotics zolpidem and zaleplon. However, unlike its predecessors, eszopiclone is not restricted to short-term treatment of insomnia. Clinical studies of up to 6 months of use show that patients do not develop tolerance to its effect. Eszopiclone is the (S)-enantiomer of zopiclone, which has been marketed as the racemic mixture in Europe for almost 20 years. These agents belong to the cyclopyrrolone class of drugs that act as agonists at the type A GABA receptor. Eszopiclone has approximately 50-fold higher binding affinity than its antipode (R)-zopiclone for GABA-A receptor (IC₅₀=21 and 1130 nM, respectively). In addition, the two enantiomers exhibit significant differences in their pharmacokinetic parameters and in vivo efficacy. In healthy volunteers, eszopiclone has 2-fold higher C_max and 2-fold greater elimination half-life than the (R)-enantiomer.The two most frequent adverse events associated with eszopiclone treatment are unpleasant taste and headache. Other less frequent side effects include somnolence, dry mouth, and nausea.

Chemical Properties

White To Pale Yellow

Originator

Aventis (France)

Uses

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.

Definition

ChEBI: The (5S)- (active) enantiomer of zopiclone. Unlike almost all other hypnotic sedatives, which are approved only for the relief of short-term (6-8 weeks) insomnia, eszopiclone is approved by the U.S. Food and Drug Administration for long-te m use.

brand name

(Pharmacia & Upjohn); Ortho-EST (Sun)Lunesta (Sepracor).

Mechanism of action

The cyclopyrrole zopiclone is described as a “superagonist” at BZRs with the subunit composition α1β2γ2 and α1β2γ3, because it potentiates the GABA-gated current more than the benzodiazepine (flunitrazepam) reference agonist. Racemic zopiclone has been available in Europe since 199,2 and the higher affinity S-enantiomer (eszopiclone) was marketed in the United States in 2005, primarily to treat insomnia, because of its rapid onset and moderate duration (half-life, ~6 hours) of hypnotic-sedative effect. Less than 10% of orally administered eszopiclone is excreted unchanged, because it undergoes extensive CYP3A4- and CYP2E1-catalyzed oxidation and demethylation to metabolites excreted primarily in urine. "

Pharmacokinetics

Zoplicone was originally marketed as a racemic mixture; however, because the sedative activity is primarily associated with the S-isomer, only the S-isomer is currently marketed in the United States (as esozoplicone) (36). It is soluble in dilute mineral acids. Unlike zolpidem and zaleplon, eszoplicone is not as specific for the α1 subunit of GABAA, but it binds broadly, like the benzodiazepines (Table 19.2). Its pharmacological and pharmacodynamic activities, however, are more closely related to those of the nonbenzodiazepines. It is rapidly absorbed, with an oral bioavailability of approximately 80%, reaching peak concentrations in 1 h and having a relatively long elimination half-life of approximately 6 hours (Table 19.2). Eszopliclone is primarily metabolized to (S)-zoplicone N-oxide and (S)-N-desmethylzoplicone by the CYP3A4. (S)-Ndesmethylzopiclone binds to GABA receptors with substantially lower potency than eszopiclone, and (S)-zopiclone-N-oxide shows no significant binding to this receptor. It does not accumulate with once-daily administration, and it exhibits linear (dose-proportional) pharmacokinetics over the range of 1 to 6 mg. Eszopiclone is weakly bound to plasma protein (52–60%), suggesting that eszopiclone distribution should not be affected by drug–drug interactions caused by protein binding. Up to 75% of an oral dose of racemic zopiclone is excreted in the urine, primarily as metabolites. A similar excretion profile would be expected for eszopiclone. Less than 10% of the orally administered eszopiclone dose is excreted in the urine as unchanged drug. After a high-fat meal, peak plasma concentrations can be delayed by approximately 1 hour without affecting its half-life.

Synthesis

The synthesis of eszopicolone involves enzymatic resolution of a zopicolone derivative to give the chiral compound as depicted in the Scheme 12. Pyrazine-2,3- dicarboxylic acid anhydride was reacted with 2-amino- 5-chloropyridine (61) in refluxing acetonitrile to generate 3- (5-chloro-2-pyridyl)carbamoyl pyrazine-2-carboxylic acid (62) in 95% yield. Compound 62 was cyclized by treating with refluxing SOCl2 to give 6-(5-chloropyrid-2-yl)-5,7- dioxo-5,6-dihydropyrrolo[3,4-b]pyrazine (63) in 79% yield.Compound 63 was subjected to partial reduction with KBH4 in dioxane-water at low temperature to give 6-(5-chloro-2- pyridyl)-7-hydroxy-5,6-dihydropyrrolo[3,4-b]pyrazin-5-one (64) in 64% yield, which was esterified with vinyl chloroformate in pyridine to give corresponding vinyl acetate 65 in 75% yield. The racemic 65 was then subjected to kinetic resolution by a highly enantioselective enzymatic hydrolysis process. Chiral vinyl acetate 67 with desired stereochemistry was obtained when candida antarctica lipase was employed for hydrolysis of 65 in dioxane/water at 60oC for 2 days. Interestingly, the enzymatic hydrolysis stopped at 50% conversion and the hydrolyzed alcohol was recovered as the starting substrate 65 because of spontaneous racemization of the alcohol in the reaction medium. Therefore, although a maximum yield of kinetic resolution is 50%, the overall efficiency of this enzymatic process is 100% because of substrate recycling. Finally, the chiral vinyl acetate 67 was condensed with methyl piperazine in acetone to give eszopicolone (IX).

Metabolism

The effects of eszoplicone on sleep onset may be reduced if it is taken either with or immediately after a high-fat/heavy meal. In elderly subjects, the elimination half-life was prolonged to approximately 5 to 9 hours. Therefore, in elderly patients, the starting dose should be decreased to 1 mg, and the dose should not exceed 2 mg. No dose adjustment is necessary in patients with renal impairment, because less than 10% of the orally administered eszopiclone dose is excreted in the urine as parent drug. Although no pharmacokinetic or pharmacodynamic or drug interactions have been reported for eszopiclone, potent inhibitors of CYP3A4 could increase plasma levels of eszopiclone. Eszopiclone does not alter the clearance of drugs metabolized by common CYP450 enzymes. Potential pharmacodynamic interactions (additive pharmacological effects) with CNS depressants such as alcohol, anticonvulsants, antihistamines, antidepressants, or other psychotropic drugs could occur. Dosage adjustment may be necessary when eszopiclone is administered with CNS depressants; concomitant use with alcohol should be avoided.
The primary advantage of eszoplicone is that it has been shown to be effective in chronic insomnia (long-term treatment) in measures of sleep latency, total sleep time, and wake time after sleep onset without development of tolerance. Eszoplicone would appear to be most effectively used for patients who tend to awaken during the night rather than patients for whom the primary problem is initiating sleep.

Eszopiclone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Eszopiclone manufacturers

Xiamen Wonderful Bio Technology Co., Ltd.

Product: Eszopiclone 138729-47-2
Price: US $66.00/KG
Min. Order: 1250KG
Purity: 99.8%
Supply Ability: 330T
Release date: 2023-07-21

Hebei Mojin Biotechnology Co., Ltd

Product: Eszopiclone 138729-47-2
Price: US $100.00/KG
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Release date: 2023-03-07

Zhejiang J&C Biological Technology Co.,Limited

Product: Eszopiclone 138729-47-2
Price: US $0.00/gram
Min. Order: 1gram
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Release date: 2022-02-17

138729-47-2, EszopicloneRelated Search:

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one Pramipexole Impurity 4 Ozagrel SEP 174559 Hydrochloride RP 48497 (Eszopiclone Impurity C) Zolpidem tartrate Alprazolam tablets Iloperidone Metabolite P88 Glucuronide (S)-(+)-2-Chlorophenylglycine methyl ester ZOPICLONE N-OXIDE 6-(5-Chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione Dextromethorphan N-Oxide N-Nordextromethorphan 3-(5-CHLOROPYRID-2-YL)CARBAMOYLPYRAZINE-2-CARBOXYLIC ACID(WXG01564) Dexzopiclone impurity 6 Dexzopiclone impurity 4 Dexzopiclone impurity 5 Pyrrole

ESOPICLONE

ESZOPICLONE

(S)-(+)-ZOPICLONE

Dexzopiclone

[(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

Lunesta

ESZOPICLONE CIV

1-Piperazinecarboxylic acid, 4-methyl-, (5S)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester (9CI)

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

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

(5S)-6-(5-CHLOROPYRID-2-YL)-5-(4-METHYLPIPERAZIN-1-YL)CARBONYLOXY-7-OXO-6,7-DIHYDRO-5H-PYRROLO[3,4-B]PYRAZINE

5S-6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-

Eszppiclone98.5%~100.5%

Eszppiclone

Zopiclone (S)-

(5S)- 6-(5-Chloropyridin-2-yl)-7-[(4-Methylpiperazin-1-yl)Carboxy] -5,6-Dihydro--Pyrrolo[3,4-b]Pyrazin-5-One

Eszopiclone CIV (100 mg)

ESZOPICLONE 99%

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

1-Piperazinecarboxylicacid, 4-Methyl-,(5S)-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-ylester

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

Zopiclone (S-enantiomer)

Eszopiclone USP/EP/BP

*Zopiclone Impurity 29(Eszopiclone)

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

Es-ZopicloneQ: What is Es-Zopiclone Q: What is the CAS Number of Es-Zopiclone Q: What is the storage condition of Es-Zopiclone Q: What are the applications of Es-Zopiclone

Eszopiclone CIV (1255850)

138729-47-2

82-52-2

GABA/Glycine receptor

Intermediates & Fine Chemicals

Pharmaceuticals

Sedative, Hypnotic