ESZOPICLONE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N05CF04
UNII UZX80K71OE
EPA CompTox DTXSID8046086

Structure

InChI Key GBBSUAFBMRNDJC-INIZCTEOSA-N
Smiles CN1CCN(C(=O)O[C@H]2c3nccnc3C(=O)N2c2ccc(Cl)cn2)CC1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H17ClN6O3
Molecular Weight 388.82
AlogP 1.57
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 91.76
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR FDA PubMed Wikipedia
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel GABA-A receptor
- - - 102 -
Assay Description Organism Bioactivity Reference
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 receptor expressed in HEK293T cells None 50.1 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-2-beta-2-gamma-2 receptor expressed in HEK293T cells None 114.0 nM
Displacement of [3H]Ro-154513 from benzodiazepine binding site of GABAA alpha-4-beta-2-gamma-2 receptor expressed in HEK293T cells None 102.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 D56C receptor mutant expressed in HEK293T cells None 82.4 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 A79C receptor mutant expressed in HEK293T cells None 393.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 T81C receptor mutant expressed in HEK293T cells None 75.2 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 T126C receptor mutant expressed in HEK293T cells None 71.9 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 M130C receptor mutant expressed in HEK293T cells None 102.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 R132C receptor mutant expressed in HEK293T cells None 110.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 L140C receptor mutant expressed in HEK293T cells None 46.3 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 T142C receptor mutant expressed in HEK293T cells None 503.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 R144C receptor mutant expressed in HEK293T cells None 174.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 X161 receptor mutant expressed in HEK293T cells None 22.4 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 R185C receptor mutant expressed in HEK293T cells None 70.9 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-1-beta-2-gamma-2 R194C receptor mutant expressed in HEK293T cells None 67.0 nM
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 F99C beta2gamma2 receptor mutant expressed in HEK293T cells None 407.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 A160C beta2gamma2 receptor mutant expressed in HEK293T cells None 60.4 nM
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha1 T162C beta-2-gamma-2 receptor mutant expressed in HEK293T cells None 33.8 nM
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 G200C beta2gamma2 receptor mutant expressed in HEK293T cells None 119.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 V202C beta2gamma2 receptor mutant expressed in HEK293T cells None 249.0 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 S204C beta2gamma2 receptor mutant expressed in HEK293T cells None 57.9 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha1 S205C beta2gamma2 receptor mutant expressed in HEK293T cells None 34.9 nM
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 T206C beta2gamma2 receptor mutant expressed in HEK293T cells None 0.83 nM
Displacement of [3H]Ro15-1788 from benzodiazepine binding site of GABAA alpha-1 V211C beta2gamma2 receptor mutant expressed in HEK293T cells None 62.4 nM
Displacement of [3H]Ro-151788 from benzodiazepine binding site of GABAA alpha-3-beta-2-gamma-2 receptor expressed in HEK293T cells None 162.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -7.93 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.26 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae -5.59 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 5.48 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 4.49 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.3 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 4.31 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -3.33 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.6665 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 %

Related Entries

Cross References

Resources Reference
ChEBI 53760
ChEMBL CHEMBL1522
DrugBank DB00402
DrugCentral 1068
FDA SRS UZX80K71OE
Human Metabolome Database HMDB0014546
Guide to Pharmacology 7429
KEGG D02624
PharmGKB PA162630444
PubChem 969472
SureChEMBL SCHEMBL28657
ZINC ZINC000019632834
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