Details of the Drug

General Information of Drug (ID: DMXYA5K)

Drug Name
Agomelatine
Synonyms
Thymanax; Valdoxan; Agomelatine [INN]; AGO 178; AGO178; S 20098; S20098; AGO-178; Agomelatine(INN); S-20098; Valdoxan (TN); Valdoxan, Melitor, Thymanax, Agomelatine; N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide; N-(2-(7-Methoxy-1-naphthalenyl)ethyl)acetamide; N-(2-(7-Methoxynaphth-1-yl)ethyl)acetamide; N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide
Indication
Disease Entry ICD 11 Status REF
Major depressive disorder 6A70.3 Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 243.3
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Bioavailability
The bioavailability of drug is 5% []
Half-life
The concentration or amount of drug in body reduced by one-half in less than 2 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C15H17NO2
IUPAC Name
N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
Canonical SMILES
CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC
InChI
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
Cross-matching ID
PubChem CID
82148
ChEBI ID
CHEBI:134990
CAS Number
138112-76-2
DrugBank ID
DB06594
TTD ID
D0Y8UB
VARIDT ID
DR00473
INTEDE ID
DR0053

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Melatonin receptor type 1A (MTNR1A) TT0WAIE MTR1A_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2)
Main DME 		DEJGDUW CP1A2_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-hydroxytryptamine receptor 2C (HTR2C) OT6H8DE0 5HT2C_HUMAN Protein Interaction/Cellular Processes [5]
Melatonin receptor type 1A (MTNR1A) OTYYV8JK MTR1A_HUMAN Protein Interaction/Cellular Processes [6]
Melatonin receptor type 1B (MTNR1B) OT6VFHX9 MTR1B_HUMAN Protein Interaction/Cellular Processes [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 06 Mental, behavioural or neurodevelopmental disorder
Disease Class ICD-11: 6A20 Schizophrenia
The Studied Tissue Pre-frontal cortex
The Studied Disease Major depressive disorder [ICD-11:6A20]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Melatonin receptor type 1A (MTNR1A) DTT MTNR1A 5.71E-01 -0.08 -0.54
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.68E-01 3.64E-02 2.72E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 198).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders. Curr Top Med Chem. 2008;8(11):954-68.
4 Does celecoxib inhibit agomelatine metabolism via CYP2C9 or CYP1A2? Drug Des Devel Ther. 2018 Jul 11;12:2169-2172.
5 Design, synthesis and pharmacological evaluation of new series of naphthalenic analogues as melatoninergic (MT1/MT2) and serotoninergic 5-HT2C dual ligands (I). Eur J Med Chem. 2012 Mar;49:310-23.
6 Synthesis of phenalene and acenaphthene derivatives as new conformationally restricted ligands for melatonin receptors. J Med Chem. 2000 Nov 2;43(22):4051-62. doi: 10.1021/jm000922c.