Ramelteon

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.

Ramelteon
Clinical data
Trade namesRozerem, others
Other namesTAK-375
AHFS/Drugs.comMonograph
MedlinePlusa605038
License data
Dependence
liability		Low
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability1.8%
Protein binding82% (mainly albumin)
MetabolismLiver (CYP1A2 major, CYP2C and CYP3A4 minor)
MetabolitesM-II (active metabolite)
Elimination half-lifeRamelteon: 1–2.6 hours
M-II: 2–5 hours
ExcretionUrine: 84%
Feces: 4%
Identifiers
  • (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno-[5,4-b]
    furan-8-yl)ethyl]propionamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.215.666
Chemical and physical data
FormulaC16H21NO2
Molar mass259.349 g·mol−1
3D model (JSmol)
  • CCC(=O)NCC[C@@H]1CCc2ccc3c(c21)CCO3
  • 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-/m1/s1 Y
  • Key:YLXDSYKOBKBWJQ-GFCCVEGCSA-N Y
  (verify)

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.

Ramelteon was first described in 2002 and was approved for medical use in 2005. Unlike certain other sleep medications, ramelteon is not a controlled substance and has no known potential for misuse.

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