Ramelteon

Ramelteon is a central nervous system (CNS) depressant medication that can help people sleep. It is used for patients that have trouble falling asleep.

Ramelteon has significant drug-drug interaction with the following drugs: amiodarone[*], ciprofloxacin[*], fluvoxamine[*], ticlopidine[*].

Ramelteon

Clinical data
Trade names	Rozerem, others
Synonyms	TAK-375
AHFS/Drugs.com	Monograph
MedlinePlus	a605038
License data	US DailyMed: Ramelteon
Dependence liability	Low[1]
Routes of administration	By mouth
ATC code	N05CH02 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances) [2] US: ℞-only [3]
Pharmacokinetic data
Bioavailability	1.8%[3]
Protein binding	82% (mainly albumin)[3]
Metabolism	Liver (CYP1A2 major, CYP2C and CYP3A4 minor)[3]
Metabolites	M-II (active metabolite)[3]
Elimination half-life	Ramelteon: 1–2.6 hours[3] M-II: 2–5 hours[3][4]
Excretion	Kidney: 84%[3] Feces: 4%[3]
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
KEGG	D02689 Y
ChEMBL	ChEMBL133775 Y
ECHA InfoCard	100.215.666
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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-/m1/s1 Y Key:YLXDSYKOBKBWJQ-GFCCVEGCSA-N Y
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1. ↑ Kim, HK; Yang, KI (December 2022). "Melatonin and melatonergic drugs in sleep disorders". Translational and Clinical Pharmacology. 30 (4): 163–171. doi:10.12793/tcp.2022.30.e21. PMC 9810491. PMID 36632077.
2. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16. {{cite web}}: line feed character in |title= at position 4 (help)
3. ↑ ^{3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8} Cite error: The named reference Rozerem FDA label was used but no text was provided for refs named (see the help page).
4. ↑ Karim A, Tolbert D, Cao C (February 2006). "Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia". Journal of Clinical Pharmacology. 46 (2): 140–148. doi:10.1177/0091270005283461. PMID 16432265. S2CID 38171735.