Eszopiclone
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Basic Info
| Common Name | Eszopiclone(F05454) |
| 2D Structure | |
| 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. |
| FRCD ID | F05454 |
| CAS Number | 138729-47-2 |
| PubChem CID | 969472 |
| Formula | C17H17ClN6O3 |
| IUPAC Name | [(7S)-6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate |
| InChI Key | GBBSUAFBMRNDJC-INIZCTEOSA-N |
| 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 |
| Canonical SMILES | CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl |
| Isomeric SMILES | CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl |
| Wikipedia | Eszopiclone |
| Synonyms |
Eszopiclone [USAN:INN]
Eszopiclone
138729-47-2
Lunesta
(S)-Zopiclone
Estorra
Esopiclone
(+)-Zopiclone
( )-Zopiclone
Lunivia
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyrrolopyrazines |
| Subclass | Cyclopyrrolones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cyclopyrrolones |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Cyclopyrrolone - Piperazine-1-carboxylic acid - 2-heteroaryl carboxamide - N-methylpiperazine - N-alkylpiperazine - Aryl chloride - Aryl halide - Imidolactam - Pyridine - Pyrazine - Piperazine - 1,4-diazinane - Heteroaromatic compound - Carbamic acid ester - Tertiary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Tertiary aliphatic amine - Tertiary amine - Lactam - Carbonic acid derivative - Azacycle - Carboxylic acid derivative - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Amine - Carbonyl group - Organopnictogen compound - Hydrocarbon derivative - Organohalogen compound - Organochloride - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as cyclopyrrolones. These are compounds belonging to a family of pyridin-2-ylpyrrole based chemicals. The pyrrole is usually fused to a benzene, pyrimidine, or dithiin. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 388.812 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Complexity | 573 |
| Monoisotopic Mass | 388.105 |
| Exact Mass | 388.105 |
| XLogP | 0.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9382 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.5805 |
| P-glycoprotein Substrate | Substrate | 0.6917 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6381 |
| Inhibitor | 0.5000 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6785 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4637 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7158 |
| CYP450 2D6 Substrate | Non-substrate | 0.9115 |
| CYP450 3A4 Substrate | Substrate | 0.6775 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8995 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6890 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7838 |
| Non-inhibitor | 0.5688 | |
| AMES Toxicity | AMES toxic | 0.5332 |
| Carcinogens | Non-carcinogens | 0.9174 |
| Fish Toxicity | High FHMT | 0.9984 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9649 |
| Honey Bee Toxicity | Low HBT | 0.8955 |
| Biodegradation | Not ready biodegradable | 0.9941 |
| Acute Oral Toxicity | III | 0.7817 |
| Carcinogenicity (Three-class) | Non-required | 0.6390 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8509 | LogS |
| Caco-2 Permeability | 1.2284 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6411 | LD50, mol/kg |
| Fish Toxicity | 1.1596 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7259 | pIGC50, ug/L |
Targets
- General Function:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
- Gene Name:
- GABRA1
- Uniprot ID:
- P14867
- Molecular Weight:
- 51801.395 Da
References
- Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [19942638 ]
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA2
- Uniprot ID:
- P47869
- Molecular Weight:
- 51325.85 Da
References
- Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [19942638 ]
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA3
- Uniprot ID:
- P34903
- Molecular Weight:
- 55164.055 Da
References
- Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [19942638 ]
- General Function:
- Sphingosine-1-phosphate receptor activity
- Specific Function:
- Receptor for the lysosphingolipid sphingosine 1-phosphate (S1P). S1P is a bioactive lysophospholipid that elicits diverse physiological effect on most types of cells and tissues. When expressed in rat HTC4 hepatoma cells, is capable of mediating S1P-induced cell proliferation and suppression of apoptosis.
- Gene Name:
- S1PR3
- Uniprot ID:
- Q99500
- Molecular Weight:
- 42249.805 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
- General Function:
- Transporter activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA5
- Uniprot ID:
- P31644
- Molecular Weight:
- 52145.645 Da
References
- Nutt DJ, Stahl SM: Searching for perfect sleep: the continuing evolution of GABAA receptor modulators as hypnotics. J Psychopharmacol. 2010 Nov;24(11):1601-12. doi: 10.1177/0269881109106927. Epub 2009 Nov 26. [19942638 ]
- General Function:
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function:
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name:
- GABRA6
- Uniprot ID:
- Q16445
- Molecular Weight:
- 51023.69 Da
References
- Hanson SM, Morlock EV, Satyshur KA, Czajkowski C: Structural requirements for eszopiclone and zolpidem binding to the gamma-aminobutyric acid type-A (GABAA) receptor are different. J Med Chem. 2008 Nov 27;51(22):7243-52. doi: 10.1021/jm800889m. [18973287 ]