Ramelteon

CB0496858 · Rozerem · N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide · (S)-N-(2-(2,6,7,8-tetrahydro-1H-indeno[5,4-b]furan-8-yl)ethyl)propionamide · DF883 · CS-1962 · TAK-375 · RAMELTEON

https://huagongshe.com/ko/chemical/208902

식별자 및 물리적 특성

CAS No.	196597-26-9
분자식	C16H21NO2
평균 분자량	259.34 g/mol
단동위원소 질량	259.15722891 g/mol
SMILES	CCC(=O)NCC[C@@H]1CCc2ccc3c(c21)CCO3
InChIKey	YLXDSYKOBKBWJQ-LBPRGKRZSA-N
PubChem CID	208902
ChEMBL	CHEMBL1218
ChEBI	CHEBI:109549
EC No.	688-929-3
DTXSID	DTXSID6045951

화학 및 물리적 성질

XLogP	2.7
극성 표면적	38.3
수소 결합 공여자 수	1
수소 결합 수용자 수	2
회전 가능 결합 수	4
무거운 원자 수	19
형식 전하	0
복잡도	331
의약품	Pharmaceuticals -> Listed in ZINC15
LogP(분배 계수)	2.42.57
Color/Form	Crystals from ethyl acetate
용해도	1.64e-02 g/L디메틸설폭사이드, 에탄올, 메탄올에 용해됨
Human Drugs	Breast FeedingLactationMilk, HumanCentral Nervous System DepressantsFDA approved drugs -> Active ingredient
녹는점	113-115 °C113-1150C
Optical Rotation	Specific optical rotation: -57.8 deg at 20 °C/D (concentration = 1.004 g/100 mL in chloroform)
Physical Description	Solid
끓는 점	455.3±24.0 °C(Predicted)
밀도	1.119±0.06 g/cm3(Predicted)
인화점	2℃
저장 조건	Sealed in dry,Store in freezer, under -20°C
물리적 상태	고체
pKa(산도 계수)	16.37±0.46(Predicted)
색상	수정 같은
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-/m0/s1
InChIKey	YLXDSYKOBKBWJQ-LBPRGKRZSA-N
SMILES	C(NCC[C@H]1C2=C3CCOC3=CC=C2CC1)(=O)CC

화학적 성질

Crystalline Solid

안전 및 규제

GHS 분류	WarningH302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory.H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including ramelteon, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and Categories	Repr. 2 (100%)Acute Tox. 4 (97.6%)
처리 방법	SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
상호 작용	Substrates of CYP isoenzymes 1A2 (e.g., theophylline), 2C9 (e.g., warfarin), 2C19 (e.g., omeprazole), 2D6 (e.g., dextromethorphan), or 3A4 (e.g., midazolam): Pharmacokinetic interaction unlikely.Inducers of CYP isoenzymes: Pharmacokinetic interaction observed during concomitant use with rifampin (decreased concentrations of ramelteon and active metabolite). Possibly reduced ramelteon efficacy when used concomitantly with potent CYP inducers such as rifampin.Inhibitors of CYP2D6 isoenzyme: Pharmacokinetic interaction with fluoxetine unlikely.Inhibitors of CYP2C9 isoenzyme: Pharmacokinetic interaction observed during concomitant use with fluconazole (increased concentrations of ramelteon and active metabolite). Caution if used concomitantly with fluconazole or other potent inhibitors of CYP2C9.

용도

개요

Ramelteon, also known as N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide, is a melatonin agonist developed by Takeda Pharmaceuticals, Inc. It was approved by the FDA for marketing in the United States in September 2005 and is marketed under the name Rozerem. It is used to treat difficult-to-sleep and short-term insomnia. Ramelteon is effective for both chronic and short-term insomnia. Unlike most treatments of insomnia that target the GABA (g-aminobutyric acid) receptor complex, ramelteon is an agonist of the melatonin receptor. In particular, it has high selectivity for the MT1 and MT2 subtypes, which have been implicated in the maintenance of circadian rhythms, over the MT3 receptor responsible for other melatonin functions. Its lack of affinity for not only the GABA receptor complex but also neurotransmitter, dopaminerigic, opiate, and benzodiazepine receptors suggests an improved safety profile devoid of the abuse potential of the hypnotic drugs that target these receptors. As such, ramelteon is not a scheduled drug.

용도

Ramelteon is a selective melatonin receptor agonist of MT1 and MT2 approved for the treatment of insomnia (trouble in sleeping). It acts as a sedative and hypnotic agent. Ramelteon is the only prescription sleep aid not designated as a Schedule IV controlled substance.

일반 설명

The melatonin molecule was modified mainly by replacing the nitrogen of the indole ring with a carbon to give an indane ring and by incorporating 5-methoxyl group in the indole ring into a more rigid furan ring. The selectivity of the resulting ramelteon for MT1 receptor is eight times more than that of MT2 receptor. Unlike melatonin, it is more effective in initiating sleep (MT1 activity) rather than to readjust the circadian rhythm (MT2 activity). It appears to be distinctly more efficacious than melatonin but less efficacious than benzodiazepines as a hypnotic. Importantly, this drug has no addiction liability (it is not a controlled substance). As a result, it has recently been approved for the treatment of insomnia.