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

• ChemBase ID: 285
• Molecular Formular: C17H17ClN6O3
• Molecular Mass: 388.80828
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate
• IUPAC Traditional name: lunesta; eszopiclone
• Brand Name: Estorra; Lunesta
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.038308
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.59504867
• LogD (pH = 7.4): 0.6902288
• Log P: 0.80654305
• Molar Refractivity: 95.8855 cm^3
• Polarizability: 37.123627 Å^3
• Polar Surface Area: 91.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.97
• LOG S: -2.64
• Solubility (Water): 8.85e-01 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol; Phosphate Buffer (pH 3.2); very slightly soluble
• Apperance: White To Pale Yellow Solid
• Melting Point: 202-204°C
• Hydrophobicity(logP): 0.8; 1.253

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95%

DETAILS

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.

REFERENCES

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