RAMELTEON

Search structure
Trade Names:
Synonyms:
Status: Approved (2005)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: N05CH02
UNII: 901AS54I69

Structure
InChI Key YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Smile CCC(=O)NCC[C@@H]1CCc2ccc3c(c21)CCO3
InChI
InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H21NO2
Molecular Weight 259.35
AlogP 2.57
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 38.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Melatonin receptor agonist
Primary Target
MT1 receptor
MT2 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 10.62
Enzyme Transferase
- - - - 3.38-27.76
Enzyme
- - - - 3.38-27.76
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -1.4--0.25
Ion channel Ligand-gated ion channel 5HT3 receptor
- - - - 6.73
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
- - - - 14.24
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine-derivative receptor (family A GPCR) Melatonin receptor
- - - 0.0138-0.014 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - - 12.36
Membrane receptor
- - - 0.0138-0.014
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- - - - 18.02
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 113.38
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 85000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Bipolar Disorder 3 D001714 ClinicalTrials
Sleep Wake Disorders 3 D012893 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Sleep Apnea, Obstructive 2 D020181 ClinicalTrials
Migraine without Aura 2 D020326 ClinicalTrials
Burns 2 D002056 ClinicalTrials
Tobacco Use Disorder 2 D014029 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Migraine with Aura 2 D020325 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Marijuana Abuse 1 D002189 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache
Nervous system disorders Headache 7.0
Cardiac disorders Dizziness 5.0
Nervous system disorders Somnolence 5.0
General disorders and administration site conditions Asthenia 4.0
Cardiac disorders Dizziness 4.0
General disorders and administration site conditions Fatigue 4.0
General disorders and administration site conditions Asthenia 3.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue 3.0
Nervous system disorders Insomnia 3.0
Gastrointestinal disorders Nausea 3.0
Nervous system disorders Somnolence
Nervous system disorders Somnolence 3.0
Infections and infestations Upper respiratory tract infection 3.0
Musculoskeletal and connective tissue disorders Arthralgia 2.0
General disorders and administration site conditions Asthenia
Psychiatric disorders Depression 2.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.0
Gastrointestinal disorders Dysgeusia 2.0
General disorders and administration site conditions Fatigue
Nervous system disorders Insomnia
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Gastrointestinal disorders Nausea
Nervous system disorders Somnolence
Infections and infestations Upper respiratory tract infection
Musculoskeletal and connective tissue disorders Arthralgia
Blood cortisol decreased 1.0
Psychiatric disorders Depression
Gastrointestinal disorders Dysgeusia
Infections and infestations Influenza 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Nervous system disorders Somnolence 0.8
Cardiac disorders Dizziness 0.5
General disorders and administration site conditions Asthenia 0.3
General disorders and administration site conditions Fatigue 0.3
Nervous system disorders Headache 0.3
Nervous system disorders Insomnia 0.3
Gastrointestinal disorders Nausea 0.3

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
18.98
Nervous system disorders
17.4
Injury, poisoning and procedural complications
16.82
Psychiatric disorders
15.57
Gastrointestinal disorders
3.83
Vascular disorders
3.75
Cardiac disorders
3.41
Skin and subcutaneous tissue disorders
2.75
Respiratory, thoracic and mediastinal disorders
2.66
Musculoskeletal and connective tissue disorders
2.58

Cross References

Resources Reference
CAS NUMBER 196597-26-9
ChEBI 109549
ChEMBL CHEMBL1218
DrugBank DB00980
DrugCentral 2355
FDA SRS 901AS54I69
Human Metabolome Database HMDB15115
Guide to Pharmacology 1356
KEGG D02689
PDB JEV
PharmGKB PA164744896
PubChem 208902
SureChEMBL SCHEMBL29237
ZINC ZINC000003960338
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