ramelteon

Also known as Rozerem®, TAK-375, TAK375, (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno-[5,4-b] furan-8-yl)ethyl]propionamide

Ramelteon, sold under the brand name Rozerem among others, is a melatonin agonist medication which is used in the treatment of insomnia. It is indicated specifically for the treatment of insomnia characterized by difficulties with sleep onset. It reduces the time taken to fall asleep, but the degree of clinical benefit is small. The medication is approved for long-term use. Ramelteon is taken by mouth.

Key facts

Drug.Verifiedfields: verified
Drug.Watchedfields: verified
Drug.verifiedrevid: 464379960
Drug.image: Ramelteon skeletal formula.svg
Drug.image_class: skin-invert-image
Drug.image2: Ramelteon ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.width2: 200
Drug.tradename: Rozerem, others
Drug.MedlinePlus: a605038
Drug.DailyMedID: Ramelteon
Drug.dependency_liability: Low
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: N05
Drug.ATC_suffix: CH02
Drug.legal_BR: C1
Drug.legal_US: Rx-only
Drug.bioavailability: 1.8%

via Wikipedia infobox

Chemical data

Formula: C16H21NO2
Molecular weight: 259.34 g/mol
IUPAC name: N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzofuran-8-yl]ethyl]propanamide
SMILES: CCC(=O)NCC[C@@H]1CCC2=C1C3=C(C=C2)OCC3
InChIKey: YLXDSYKOBKBWJQ-LBPRGKRZSA-N
XLogP: 2.7
Polar surface area: 38.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

~13 min read

Encyclopedic overview

24 sections

Contents

Medical uses
Insomnia
Circadian rhythm sleep disorders
Other uses
Delirium
Bipolar disorder
Available forms
Contraindications
Adverse effects
Overdose
Interactions
Pharmacology
Pharmacodynamics
Mechanism of action
Pharmacokinetics
Absorption
Distribution
Metabolism
Elimination
Special populations
History
Society and culture
Research
References

Side effects of ramelteon include somnolence, dizziness, fatigue, nausea, exacerbated insomnia, and changes in hormone levels. Ramelteon is an analogue of melatonin and is a selective agonist of the melatonin MT1 and MT2 receptors. The half-life and duration of ramelteon are much longer than those of melatonin. Ramelteon is not a benzodiazepine or Z-drug and does not interact with GABA receptors, instead having a distinct mechanism of action.

Excerpted from Wikipedia’s “ramelteon” article, available under the CC BY-SA 4.0 licence.

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