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Compound Detail

CHEMBL1218

RAMELTEON
💊 Approved Drug
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💊 Approved Drug
CCC(=O)NCC[C@@H]1CCc2ccc3c(c21)CCO3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1218
Name RAMELTEON
Phase Approved
Structure Type MOL
InChI Key YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Therapeutic ✓ Yes

Known Names

Ramelteon Rozerem TAK-375 TAK375
7
Targets
13
Activities
3
Assay Types
8
PK Parameters
20
Publications
4
Known Names
13
Indications
1
Mechanisms

Molecular Properties

259.4
MW (Da)
2.57
ALogP
2
HBA
1
HBD
38.3
PSA (Ų)
0.90
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Stem -melteon
USAN Year 2004

Extended Properties

Molecular Formula C16H21NO2
MW 259.35
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.17

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Melatonin receptor agonist AGONIST Melatonin receptor ✓ ✓

Indications

Sleep Initiation and Maintenance Disorders Bipolar Disorder Depressive Disorder Sleep Wake Disorders Burns Migraine with Aura Migraine without Aura Pulmonary Disease, Chronic Obstructive Severe Acute Respiratory Syndrome Sleep Apnea, Obstructive Substance-Related Disorders Tobacco Use Disorder Marijuana Abuse

ATC Classification

N05CH02
ramelteon
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

Ki 9 meas. best 10.86
EC50 2 meas. best 9.05
IC50 2 meas. best 10.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Melatonin receptor type 1A
CHEMBL1945
 Ki 10.86 10.855 0.0 2
Melatonin receptor
CHEMBL2094268
 Ki 10.86 10.86 0.0 1
Rattus norvegicus
CHEMBL376
 IC50 10.68 10.68 0.0 1
Unchecked
CHEMBL612545
 Ki 10.52 8.2667 0.0 3
Melatonin receptor type 1B
CHEMBL1946
 Ki 10.35 10.15 0.0 2
Unchecked
CHEMBL612545
 EC50 9.05 8.78 0.9 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.05 5.05 8846.1 1
Bile salt export pump
CHEMBL6020
 IC50 4.07 4.07 85000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 47.0 uL/min Homo sapiens
CL 60.0 uL/min Rattus norvegicus
CL 51.0 mL.min-1.g-1 Homo sapiens
CL 126.0 mL.min-1.g-1 Rattus norvegicus
F 1.8 % Homo sapiens
F 8.5 % Rattus norvegicus
T1/2 0.83 hr Homo sapiens
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Melatonin receptor Ki = 0.0138 nM 10.86 Binding affinity against human Melatonin receptor type 1A (MT1) in CHO cells 12213063
Melatonin receptor type 1A Ki = 0.0138 nM 10.86 Binding affinity against human Melatonin receptor type 1A (MT1) 12213063
Melatonin receptor type 1A Ki = 0.014 nM 10.85 Binding affinity to human MT1 expressed in CHO cells 33682410
Rattus norvegicus IC50 = 0.0208 nM 10.68 Inhibition of forskolin stimulated cAMP production in neonatal rat pituitary 12213063
Unchecked Ki = 0.03 nM 10.52 Displacement of [3H]melatonin from rat MT2 receptor expressed in CHO-Galpha16 ce... 21237644
Melatonin receptor type 1B Ki = 0.045 nM 10.35 Binding affinity against human Melatonin receptor type 1B (MT2) 12213063
Melatonin receptor type 1B Ki = 0.112 nM 9.95 Binding affinity to human MT2 expressed in CHO cells 33682410
Unchecked EC50 = 0.89 nM 9.05 Binding affinity to rat MT2 receptor expressed in CHO-Galpha16 cells assessed as... 21237644
Unchecked Ki = 2.0 nM 8.7 Displacement of [3H]melatonin from rat MT1 receptor expressed in CHO-Galpha16 ce... 21237644
Unchecked EC50 = 3.1 nM 8.51 Binding affinity to rat MT1 receptor expressed in CHO-Galpha16 cells assessed as... 21237644
Unchecked Ki = 2600.0 nM 5.58 Binding affinity against Melatonin receptor 3 (MT3) of Syrian hamster brain and ... 12213063
Sigma non-opioid intracellular receptor 1 Ki = 8846.06 nM 5.05 PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra... -
Bile salt export pump IC50 = 85000.0 nM 4.07 Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21... 22961681

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
- 10.6019/CHEMBL5058564 Fibroblast 10
33626870 10.1021/acs.jmedchem.0c00627 ADMET 9
33682410 10.1021/acs.jmedchem.0c01836 ADMET 6
21237644 10.1016/j.bmcl.2010.12.068 Unchecked 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
- 10.6019/CHEMBL5058564 U2OS 5
- 10.6019/CHEMBL5058564 HEK-293T 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
31307886 10.1016/j.bmcl.2019.06.043 ADMET 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
21237644 10.1016/j.bmcl.2010.12.068 Liver microsomes 2
12213063 10.1021/jm0201159 Melatonin receptor type 1A 2

Data from ChEMBL 36 via Core Engine