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

General Information of Drug (ID: DR0053)
Drug Name
Agomelatine
Synonyms
Agomelatine; Agomelatine [INN]; Melitor; S 20098; S-20098; S20098; Thymanax; Valdoxan; YJYPHIXNFHFHND-UHFFFAOYSA-N; 137R1N49AD; 138112-76-2; AGO-178; Acetamide, N-[2-(7-methoxy-1-naphthalenyl)ethyl]-; C15H17NO2; CHEMBL10878; N-(2-(7-Methoxy-1-naphthalenyl)ethyl)acetamide; N-(2-(7-Methoxynaphth-1-yl)ethyl)acetamide; N-(2-(7-Methoxynaphthalen-1-yl)ethyl)acetamide; N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide; N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide; N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide; UNII-137R1N49AD
Indication Depression [ICD11: 6A71] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 243.3 Topological Polar Surface Area 38.3
Heavy Atom Count 18 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
82148
PubChem SID
7980554 ; 10219207 ; 12014766 ; 15121987 ; 17396749 ; 43137308 ; 47805575 ; 48029689 ; 48253997 ; 48329090 ; 49859801 ; 50597493 ; 53789947 ; 57333351 ; 58107135 ; 85175740 ; 85209276 ; 92720043 ; 99437046 ; 103171284 ; 103943227 ; 104379867 ; 109692881 ; 123121579 ; 124757110 ; 125163914 ; 125333716 ; 126620366 ; 126648120 ; 126667094 ; 126728359 ; 129806556 ; 131480735 ; 134338989 ; 135037533 ; 135588690 ; 135649906 ; 136340261 ; 136367368 ; 136368118 ; 136991142 ; 137228670 ; 137232583 ; 142374863 ; 144115558 ; 144160950 ; 152225873 ; 152258747 ; 152344557 ; 160647592
ChEBI ID
CHEBI:134990
CAS Number
138112-76-2
TTD Drug ID
D0Y8UB
Formula
C15H17NO2
Canonical SMILES
CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC
InChI
1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)
InChIKey
YJYPHIXNFHFHND-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
Agomelatine metabolite M1 DM001540 N. A. Oxidation - Monohydroxylation 1 [3]
Agomelatine metabolite M5 DM001537 N. A. Oxidation - Demethylation 1 [3]
Agomelatine metabolite M37 DM001541 N. A. Oxidation - Dealkylation 2 [3]
Agomelatine metabolite M6 DM001538 N. A. Oxidation - Monohydroxylation 2 [3]
Agomelatine metabolite M38 DM001539 N. A. Oxidation - Oxidative Dealkylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000103 Agomelatine Agomelatine metabolite M5 Oxidation - Demethylation CYP2C19 [3]
MR000104 Agomelatine Agomelatine metabolite M1 Oxidation - Monohydroxylation Unclear [3]
MR000102 Agomelatine metabolite M1 Agomelatine metabolite M37 Oxidation - Dealkylation Unclear [3]
MR000100 Agomelatine metabolite M5 Agomelatine metabolite M6 Oxidation - Monohydroxylation Unclear [3]
MR000101 Agomelatine metabolite M6 Agomelatine metabolite M38 Oxidation - Oxidative Dealkylation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
References
1 Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92.
2 Does celecoxib inhibit agomelatine metabolism via CYP2C9 or CYP1A2? Drug Des Devel Ther. 2018 Jul 11;12:2169-2172.
3 Characterizing novel metabolic pathways of melatonin receptor agonist agomelatine using metabolomic approaches Biochem Pharmacol. 2016 Jun 1;109:70-82. doi: 10.1016/j.bcp.2016.03.020.

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