Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0652)
Drug Name
Eszopiclone
Synonyms
Esopiclone; Estorra; Eszopiclone; Eszopiclone [USAN:INN]; Lunesta; SEP-190; SEP-225441; UZX80K71OE; ( )-Zopiclone; (+)-Zopiclone; (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-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate; (S)-Zopiclone; 138729-47-2; CHEBI:53760; HSDB 7472; UNII-UZX80K71OE; [(7S)-6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 388.8 Topological Polar Surface Area 91.8
Heavy Atom Count 27 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
969472
PubChem SID
8719708 ; 12015386 ; 14927588 ; 17396794 ; 25819909 ; 26612818 ; 29215492 ; 44256005 ; 46505809 ; 49666409 ; 50070163 ; 50070571 ; 50071326 ; 57408900 ; 61128015 ; 75503740 ; 87246620 ; 89736090 ; 92714227 ; 103558705 ; 104170161 ; 110105491 ; 117478867 ; 121362188 ; 121362390 ; 125169642 ; 126592991 ; 126627684 ; 126629616 ; 126655556 ; 131298420 ; 131378756 ; 134221729 ; 135114014 ; 135696725 ; 137002949 ; 141949765 ; 144205286 ; 152035015 ; 160963748 ; 162957823 ; 164196530 ; 164832496 ; 170465445 ; 172080786 ; 175265884 ; 175271194 ; 175610981 ; 178104001 ; 179149892
ChEBI ID
CHEBI:53760
CAS Number
138729-47-2
TTD Drug ID
D06ZII
Formula
C17H17ClN6O3
Canonical SMILES
CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-amino-5-chloropyridine DM000906
66174
Unclear 1 [6]
CO2 DM000908
280
Oxidation - Oxidative Decarboxylation 1 [7]
N-desmethylzopiclone DM000907
162892
Oxidation - N-Demethylation 1 [6]
Zopiclone N-oxide DM000905
162548
Oxidation - N-Oxidation 1 [6]
2-amino-5-chloropyridine DM000906
66174
Unclear 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002711 Eszopiclone Zopiclone N-oxide Oxidation - N-Oxidation CYP3A4 ... [6]
MR002712 Eszopiclone 2-amino-5-chloropyridine Unclear Unclear [6]
MR002713 Eszopiclone N-desmethylzopiclone Oxidation - N-Demethylation CYP3A4 ... [6]
MR002714 Eszopiclone Carbon dioxide Oxidation - Oxidative Decarboxylation Unclear [7]
MR002710 N-desmethylzopiclone 2-amino-5-chloropyridine Unclear Unclear [6]
MR002709 Zopiclone N-oxide 2-amino-5-chloropyridine Unclear Unclear [6]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [5]
⏷ Show the Full List of 13  DME(s)
References
1 Eszopiclone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development Curr Med Chem. 2009;16(27):3480-675. doi: 10.2174/092986709789057635.
4 Eszopiclone, a nonbenzodiazepine sedative-hypnotic agent for the treatment of transient and chronic insomnia. Clin Ther. 2006 Apr;28(4):491-516.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Development of a novel tandem mass spectrometry method for the quantification of eszopiclone without interference from 2-amino-5-chloropyridine and application in a pharmacokinetic study of rat J Pharm Biomed Anal. 2020 Sep 5;188:113363. doi: 10.1016/j.jpba.2020.113363.
7 IMOVANE (Zopiclone) Product Monograph

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