Ramelteon

Structural formula
General
Non-proprietary name	Ramelteon
other names	( S ) - N - [2- (1,6,7,8-tetrahydro-2 H -indeno [5,4- b ] furan-8-yl) ethyl] propionic acid amide
Molecular formula	C 16 H 21 NO 2
External identifiers / databases
EC number	688-929-3
ECHA InfoCard	100.215.666
PubChem	208902
ChemSpider	181000
DrugBank	DB00980
Wikidata	Q417689
Drug information
ATC code	N05 CH02
Drug class	Hypnotics
properties
Molar mass	259.34 g · mol -1
Physical state	firmly
Melting point	113-115 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-361fd
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ramelteon (trade name: Rozerem (USA), manufacturer: Takeda ) is an active ingredient structurally related to melatonin for the treatment of insomnia and sleep disorders .

pharmacology

Ramelteon is a melatonin receptor agonist , which binds with high affinity to the melatonin receptors MT ₁ and MT ₂ (low affinity for MT ₃ ) and thus promotes sleep, as these receptors influence the sleep-wake cycle.

Ramelteon has no noteworthy affinity to the GABA receptor complex or to receptors that bind neuropeptides , cytokines , serotonin , dopamine , noradrenaline , acetylcholine or opiates .

It is not yet clear whether Ramelteon is safer and more effective than melatonin . Melatonin has a similar biological function. There is evidence of greater safety compared to benzodiazepines . It reduces the time it takes to fall asleep by only 15 minutes; the shortening of the time to fall asleep corresponds to that of eszopiclone .

Ramelteon can cause hyperprolactinemia and, at high doses, is evident in animal experiments due to its carcinogenicity and teratogenicity .

Admission process

At the end of May 2008 , the advisory committee of the European Medicines Agency , which is responsible for evaluating new active substances, recommended that Ramelteon should be refused approval for the EU area due to the poor effectiveness of Ramelteon. The manufacturer then withdrew the application for approval.

literature

RT Owen: Ramelteon: Profile of a new sleep-promoting medication . In: Drugs of Today . tape 42 , no. 4 , 2006, p. 255–263 , doi : 10.1358 / dot.2006.42.4.970842 .
Synthesis: T. Yamano, M. Yamashita, M. Adachi, M. Tanaka, K. Matsumoto, M. Kawanda, O. Uchikawa, K. Fukatsu, S. Ohkawa: Approach to the stereoselective synthesis of melatonin receptor agonist Ramelteon via asymmetric hydrogenation . In: Tetrahedron: Asymmetry 17 (2006) 184-190, doi: 10.1016 / j.tetasy.2005.11.005 .
Pharmacology: K. Kato, K. Hirai, K. Nishivama, O. Uchikawa, K. Fukatsu, S. Ohkawa, Y. Kawamata, S. Hinuma, M. Miyamoto: Neurochemical properties of ramelteon (TAK-375), a selective MT1 / MT2 receptor agonist . In: Neuropharmacology 48 (2005) 301-310, doi: 10.1016 / j.neuropharm.2004.09.007 .
Usage: NL Borja, KL Daniel: Ramelteon for the treatment of insomnia . In: Clinical Therapeutics 28 (2006) 1540-1555, doi: 10.1016 / j.clinthera.2006.10.016 .
Patents: WO9732871, US6034239
Rating: Ramelteon . Prescrire International 17: 183-186 (2008).

Web links

Ramelteon at Medknowledge

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1395, ISBN 978-0-911910-00-1 .

↑ There is not yet a harmonized classification for this substance . A labeling of (S) -N- [2- (1,6,7,8-tetrahydro-2H-indeno [5,4-b] furan-8-yl) ethyl] propionamide is shown, which is derived from a self-classification by distributors in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 9, 2018.

↑ Lisa M. Schwartz, Steven Woloshin: Lost in Transmission - FDA Drug Information That Never Reaches Clinicians Archived from the original on October 27, 2010. Information: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. (Online) In: NEJM.org (Ed.): New England Journal of Medicine . 361, No. 18, October 2009, pp. 1717-1720. doi : 10.1056 / NEJMp0907708 . PMID 19846841 . Retrieved December 6, 2010. @1@ 2

↑ Questions and Answers on Recommendation for the Refusal of the Marketing Authorization for RAMELTEON. EMEA, May 30, 2008 (PDF; 35 kB).

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1395, ISBN 978-0-911910-00-1 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (S) -N- [2- (1,6,7,8-tetrahydro-2H-indeno [5,4-b] furan-8-yl) ethyl] propionamide is shown, which is derived from a self-classification by distributors in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on April 9, 2018.