 | | Eszopiclone | | Systematic (IUPAC) name | [(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 | | Identifiers | | CAS number | 138729-47-2 | | ATC code | N05CF01 | | PubChem | 969472 | | DrugBank | APRD00431 | | Chemical data | | Formula | C17H17ClN6O3 | | Mol. mass | 388.808 g/mol | | Pharmacokinetic data | | Bioavailability | ? | | Protein binding | 52-59% | | Metabolism | Hepatic oxidation and demethylation (CYP3A4 and CYP2E1-mediated) | | Half life | 6 hours | | Excretion | Renal | | Therapeutic considerations | | Pregnancy cat. | C (U.S.) Image File history File links Eszopiclone. ...
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
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The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ...
A section of the Anatomical Therapeutic Chemical Classification System. ...
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A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...
General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ...
General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ...
General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ...
General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...
General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ...
The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...
BIC pen cap, about 1 gram. ...
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In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ...
seadonkey rules =P ...
Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ...
The liver is an organ present in vertebrates and some other animals. ...
The most fundamental reactions in chemistry are the redox processes. ...
Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ...
Cytochrome P450 2E1 (abbreviated CYP2E1) (EC 1. ...
It has been suggested that Effective half-life be merged into this article or section. ...
Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ...
It has been suggested that Renal anomalies and Renal plasma threshold be merged into this article or section. ...
The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
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| | Legal status | Schedule IV (U.S.) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ...
| | Routes | Oral | Eszopiclone, marketed by Sepracorand marco 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 does not lose its effectiveness with long-term use, unlike almost all other hypnotic sedatives, which are invariably prescribed for the relief of short-term (6-8 weeks) insomnia. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ...
Sepracor, Inc. ...
Marco is the Italian version of the personal name Mark. It can be: Marco, a city in Northern Portugal Marco, a Portuguese football club Marco, a Roman praetorian guard Marco is a small Italian boy who travels to Argentina in Edmondo de Amiciss Cuore (and in the derived anime...
Hypnotic drugs are a class of drugs that induce sleep, used in the treatment of severe insomnia. ...
A sedative is a substance which depresses the central nervous system (CNS), resulting in calmness, relaxation, reduction of anxiety, sleepiness, slowed breathing, slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. ...
This article is about the sleeping disorder. ...
Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ...
Zopiclone (trade names: Imovaneâ„¢ and Zimovaneâ„¢) is a novel hypnotic agent used in the treatment of insomnia. ...
Cyclopyrrones are a class of sedative hypnotic drugs. ...
Eszopiclone may be less effective than traditional sleep-aids such as benzodiazepines, but it has several significant advantages. In addition to its suitability for long-term use, it lacks most of the abuse potential and withdrawal symptoms of the benzodiazepines, which are often diverted to recreational use because of their euphoric side effects. Alprazolam 2mg tablets The benzodiazepines (pronounced , or benzos for short) are a class of psychoactive drugs considered as minor tranquilizers with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties, which are brought on by slowing down the central nervous system. ...
Pharmacodynamics
Eszopiclone is a hypnotic with a chemical structure unrelated to benzodiazepines or other drugs with known hypnotic properties. It is an agonist for the same family of receptors as benzodiazepines, but selectively binds to the receptor subtype known as omega¹. It is believed that this selectivity is responsible for its strong hypnotic effects and lack of significant anxiolytic properties. [1]
Pharmacokinetics The pharmacokinetics of eszopiclone have been investigated in healthy subjects (adult and elderly) and in patients with hepatic disease or renal disease. In healthy subjects, the pharmacokinetic profile was examined after single doses of up to 7.5 mg and after once-daily administration of 1, 3, and 6 mg for 7 days. Eszopiclone is rapidly absorbed, with a time to peak concentration (T-max) of approximately 1 hour and a terminal-phase elimination half-life (t½) of approximately 6 hours. In healthy adults, Lunesta does not accumulate with once-daily administration, and its exposure is dose-proportional over the range of 1 to 6 mg. In patients 65 years of age and older, there is a slight prolonged elimination of eszopiclone (t½ of approximately 9 hours). Therefore, in elderly patients the starting dose of Lunesta should be decreased to 1 mg and the dose should not exceed 2 mg. Pharmacokinetics is a branch of pharmacology dedicated to the study of the time course of substances and their relationship with an organism or system. ...
Absorption Eszopiclone is rapidly absorbed following oral administration. Peak plasma concentrations are achieved within approximately 1 hour after oral administration. Eszopiclone is weakly bound to plasma protein (52-59%). The large free fraction suggests that eszopiclone disposition should not be affected by drug-drug interactions caused by protein binding. The blood-to-plasma ratio for eszopiclone is less than one, indicating no selective uptake by red blood cells.
Metabolism Following oral administration, eszopiclone is extensively metabolized by oxidation and demethylation. The primary plasma metabolites are (S)-zopiclone-N-oxide and (S)-N-desmethyl zopiclone; the latter compound binds to GABA receptors with substantially lower potency than eszopiclone, and the former compound shows no significant binding to this receptor. In vitro studies have shown that CYP3A4 and CYP2E1 enzymes are involved in the metabolism of eszopiclone. Eszopiclone did not show any inhibitory potential on CYP450 1A2, 2A6, 2C9, 2C19, 2D6, 2E1, and 3A4 in cryopreserved human hepatocytes. Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ...
Cytochrome P450 2E1 (abbreviated CYP2E1) (EC 1. ...
Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...
After oral administration, eszopiclone is eliminated with a mean t½ of approximately 6 hours. 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, the S-isomer of racemic zopiclone. Less than 10% of the orally administered eszopiclone dose is excreted in the urine as parent drug.
In healthy adults, administration of a 3 mg dose of eszopiclone after a high-fat meal resulted in no change in AUC, a reduction in mean Cmax of 21%, and delayed T-max by approximately 1 hour. The half-life remained unchanged, approximately 6 hours. The effects of Lunesta on sleep onset may be reduced if it is taken with or immediately after a high-fat/heavy meal. Sepracor, the drug's manufacturer and developer, recommend against using eszopiclone immediately following a meal due to this interference.
See also Zopiclone (trade names: Imovaneâ„¢ and Zimovaneâ„¢) is a novel hypnotic agent used in the treatment of insomnia. ...
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