Ramelteon

Ramelteon
Clinical data


Trade names	Rozerem
AHFS/Drugs.com	Monograph
MedlinePlus	a605038
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral (tablets)
ATC code	N05CH02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	1.8%
Protein binding	~82%
Metabolism	Hepatic (CYP1A2-mediated)
Biological half-life	1–2.6 hours
Excretion	Renal (84%) and fecal (4%)
Identifiers
IUPAC name (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno-[5,4-b] furan-8-yl)ethyl]propionamide
CAS Number	196597-26-9^Y
PubChem (CID)	208902
IUPHAR/BPS	1356
DrugBank	DB00980^Y
ChemSpider	9033484^Y
UNII	901AS54I69^Y
KEGG	D02689^Y
ChEMBL	CHEMBL133775^Y
ECHA InfoCard	100.215.666
Chemical and physical data
Formula	C₁₆H₂₁NO₂
Molar mass	259.343 g/mol
3D model (Jmol)	Interactive image
SMILES CCC(NCC[C@@H]1CCC2=CC=C3OCCC3=C12)=O
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-/m1/s1^Y Key:YLXDSYKOBKBWJQ-GFCCVEGCSA-N^Y

Ramelteon, marketed as Rozerem by Takeda Pharmaceuticals North America, is a sleep agent that selectively binds to the MT₁ and MT₂ receptors in the suprachiasmatic nucleus (SCN), instead of binding to GABA_A receptors, such as with drugs like zolpidem.

It however does not appear to speed the onset of sleep or the amount of sleep a person gets. It is approved by the U.S. Food and Drug Administration (FDA) for long-term use.

Ramelteon does not show any appreciable binding to GABA_A receptors, which are associated with anxiolytic, myorelaxant, and amnesic effects.

Ramelteon can be used for insomnia, particularly delayed sleep onset. It however does not appear to speed the onset of sleep or the amount of sleep a person gets.

A systematic review, published in 2014, concluded "ramelteon was found to be beneficial in preventing delirium in medically ill individuals when compared to placebo."

Ramelteon has not been shown to produce dependence and has shown no potential for abuse, and the withdrawal and rebound insomnia that is typical with GABA modulators is not present in ramelteon.

Six percent of ramelteon-treated patients in clinical trials discontinued due to an adverse event, compared to 2% in the placebo arms. The most frequent adverse events leading to discontinuation were somnolence, dizziness, nausea, fatigue, headache, and insomnia. The United States official Prescribing Information warns of rare cases of anaphylactic reactions, abnormal thinking, and suicide in patients with pre-existing depression.

In mice treated with ramelteon for two years, increases in liver and testicular tumors were observed, but only at doses at least 20 times greater than the recommended human dose on a milligram/kilogram basis.

Ramelteon has been evaluated for potential drug interactions with the following medications and showed no significant effects: omeprazole, theophylline, dextromethorphan, and midazolam, digoxin and warfarin. There were no clinically meaningful effects when ramelteon was coadministered with any of these drugs.

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Wikipedia