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

General Information of Drug (ID: DR1738)
Drug Name
Zopiclone
Synonyms
Zimovane; Zopiclona; Zopiclona [INN-Spanish]; Zopiclone [BAN:INN:JAN]; Zopiclonum; Zopiclonum [INN-Latin]; Amoban; Amovane; Imovane; RP 27267; RP-27267; Ximovan; zopiclone; (+-)-Zopiclone; 43200-80-2; 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate; BRN 0768704; C17H17ClN6O3; EINECS 256-138-9; MLS000083579; [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate
Indication Insomnia [ICD11: 7A00] Phase 4 [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
5735
PubChem SID
855666 ; 866104 ; 5375172 ; 7848435 ; 7849623 ; 7980919 ; 8153516 ; 10522775 ; 12013157 ; 14780617 ; 17405824 ; 24278148 ; 26747152 ; 26752065 ; 29224772 ; 46505233 ; 47656611 ; 47805060 ; 48403964 ; 50011925 ; 50085854 ; 50085966 ; 53778376 ; 56313660 ; 57309681 ; 75503738 ; 81093136 ; 85788133 ; 87246425 ; 92303207 ; 99437272 ; 103372219 ; 103950786 ; 104310106 ; 117795243 ; 124750371 ; 124757255 ; 124881860 ; 124881861 ; 124881862 ; 125164059 ; 125307796 ; 125325469 ; 125340634 ; 125350552 ; 126666542 ; 131803007 ; 134337723 ; 135001647 ; 135697518
ChEBI ID
CHEBI:32315
CAS Number
43200-80-2
TTD Drug ID
D0ZB7K
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
InChIKey
GBBSUAFBMRNDJC-UHFFFAOYSA-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
CO2 DM000908
280
Oxidation - Oxidative decarboxylation 1 [4]
N-desmethylzopiclone DM000907
162892
Oxidation - N-demethylation 1 [4] , [5]
Zopiclone N-oxide DM000905
162548
Oxidation - N-oxidation 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009649 Zopiclone Zopiclone N-oxide Oxidation - N-oxidation CYP3A4 ... [4], [5]
MR009650 Zopiclone Carbon dioxide Oxidation - Oxidative decarboxylation Unclear [4]
MR009651 Zopiclone N-desmethylzopiclone Oxidation - N-demethylation CYP3A4 ... [4], [5]
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
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[4]
References
1 ClinicalTrials.gov (NCT02807922) Pharmacological Treatment of Insomnia in Palliative Care.
2 Cytochrome P-450 3A4 and 2C8 are involved in zopiclone metabolism. Drug Metab Dispos. 1999 Sep;27(9):1068-73.
3 Eszopiclone, a nonbenzodiazepine sedative-hypnotic agent for the treatment of transient and chronic insomnia. Clin Ther. 2006 Apr;28(4):491-516.
4 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.
5 Distribution of zopiclone and main metabolites in hair following a single dose

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