Ramelteon is the first in a new class of sleep agents that selectively binds to the melatonin receptors in the suprachiasmatic nucleus (SCN). It is used for insomnia, particularly delayed sleep onset. Ramelteon has not been shown to produce dependence and has shown no potential for abuse.

Structure

Similar Structures

Synonyms

Ramelteon

External IDs

TAK-375 / TAK375

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Rozerem	Tablet, film coated	8 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2011-05-18	2017-06-01
Rozerem	Tablet, film coated	8 mg/1	Oral	Avera McKennan Hospital	2015-03-05	2018-07-11
Rozerem	Tablet, film coated	8 mg/1	Oral	Rebel Distributors	2005-07-22	Not applicable
Rozerem	Tablet, film coated	8 mg/1	Oral	Takeda Pharmaceuticals America, Inc.	2005-07-22	Not applicable
Rozerem	Tablet, film coated	8 mg/1	Oral	Physicians Total Care, Inc.	2006-08-01	Not applicable
Rozerem	Tablet, film coated	8 mg/1	Oral	bryant ranch prepack	2005-07-22	Not applicable
Rozerem	Tablet, film coated	8 mg/1	Oral	Carilion Materials Management	2005-07-22	Not applicable

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Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Ramelteon	Tablet	8 mg/1	Oral	Cadila Healthcare Limited	2019-07-23	Not applicable
Ramelteon	Tablet	8 mg/1	Oral	Zydus Pharmaceuticals (USA) Inc.	2019-07-23	Not applicable
Ramelteon	Tablet	8 mg/1	Oral	Dr.Reddys Laboratories Inc	2019-07-22	Not applicable
Ramelteon	Tablet	8 mg/1	Oral	Actavis Pharma, Inc.	2019-07-22	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

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Categories

UNII

901AS54I69

CAS number

196597-26-9

Weight

Average: 259.3434
Monoisotopic: 259.157228921

Chemical Formula

C₁₆H₂₁NO₂

InChI Key

YLXDSYKOBKBWJQ-LBPRGKRZSA-N

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

IUPAC Name

N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}propanamide

SMILES

CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2

Pharmacology

Indication

For the treatment of insomnia characterized by difficulty with sleep onset.

Associated Conditions

Insomnia

Pharmacodynamics

Ramelteon is the first selective melatonin agonist. It works by mimicking melatonin (MT), a naturally occuring hormone that is produced during the sleep period and thought to be responsible for the regulation of circadian rhythm underlying the normal sleep-wake cycle. Ramelteon has a high affinity for the MT₁ and MT₂ receptors. The MT₁ and MT₂ receptors are located in the brain's suprachiasmatic nuclei (SCN),which is known as the body's "master clock" because it regulates the 24-hour sleep-wake cycle. Ramelteon has an active metabolite that is less potent but circulates in higher concentrations than the parent compound. The metabolite also has weak affinity for the 5HT2b receptor.

Mechanism of action

Ramelteon is a melatonin receptor agonist with both high affinity for melatonin MT₁ and MT₂ receptors, and lower selectivity for the MT₃ receptor. Melatonin production is concurrent with nocturnal sleep, meaning that an increase in melatonin levels is related to the onset of self-reported sleepiness and an increase in sleep propensity. MT₁ receptors are believed to be responsible for regulation of sleepiness and facilitation of sleep onset, and MT₂ receptors are believed to mediate phase-shifting effects of melatonin on the circadian rhythm. While MT₁ and MT₂ receptors are associated with the sleep-wake cycle, MT₃ has a completely different profile, and therefore is not likely to be involved in the sleep-wake cycle. Remelteon has no appreciable affinity for the gamma-aminobutyric acid (GABA) receptor complex or receptors that bind neuropeptides, cytokines, serotonin, dopamine, norepinephrine, acetylcholine, or opiates.

Target	Actions	Organism
AMelatonin receptor type 1A	multitarget	Humans
AMelatonin receptor type 1B	multitarget	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Rapid, total absorption is at least 84%.

Volume of distribution

73.6 L

Protein binding

~82% (in human serum)

Metabolism

Hepatic

Route of elimination

Following oral administration of radiolabeled ramelteon, 84% of total radioactivity was excreted in urine and approximately 4% in feces, resulting in a mean recovery of 88%. Less than 0.1% of the dose was excreted in urine and feces as the parent compound.

Half life

~1-2.6 hours

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Ramelteon.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Ramelteon.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Ramelteon is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Ramelteon is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Ramelteon is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Ramelteon is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Ramelteon.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Ramelteon is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Ramelteon is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
8-azaguanine	The metabolism of 8-azaguanine can be decreased when combined with Ramelteon.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Avoid alcohol.
Do not take with or immediately after a high-fat meal.

References

Synthesis Reference

Vinod Kumar Kansal, Dhirenkumar N. Mistry, Sanjay L. Vasoya, "Intermediates and processes for the synthesis of Ramelteon." U.S. Patent US20080242877, issued October 02, 2008.

US20080242877

General References

Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650]
Simpson D, Curran MP: Ramelteon: a review of its use in insomnia. Drugs. 2008;68(13):1901-19. [PubMed:18729542]

External Links

Human Metabolome Database: HMDB0015115
PubChem Compound: 208902
PubChem Substance: 46505923
ChemSpider: 181000
BindingDB: 50118470
ChEBI: 109549
ChEMBL: CHEMBL1218
Therapeutic Targets Database: DAP000070
PharmGKB: PA164744896
Guide to Pharmacology: GtP Drug Page
HET: JEV
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Ramelteon

ATC Codes

N05CH02 — Ramelteon

PDB Entries

6me2 / 6me9

FDA label

Download (2.36 MB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Insomnia	1
1	Completed	Basic Science	Marijuana Dependence	1
1	Completed	Prevention	Insomnia	1
2	Completed	Prevention	Amnestic / Cognitive Disorders / Delayed Emergence From Anesthesia / Delirium / Delirium, Dementia / Delirium, Dementia, Amnestic, Cognitive Disorders	1
2	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
2	Completed	Treatment	Insomnia Chronic	2
2	Completed	Treatment	OSAS (Obstructive Sleep Apneas Syndrome)	1
2	Completed	Treatment	Sleep Disorder	1
2	Completed	Treatment	Sleep Disorders, Circadian Rhythm	1
2	Completed	Treatment	Sleep Initiation and Maintenance Disorders	2
2	Completed	Treatment	Minor burns / Sleep	1
2	Completed	Treatment	Substance Abuse	1
2	Completed	Treatment	Tobacco Use Disorders	1
2	Terminated	Prevention	Migraine / Migraine With Aura / Migraine Without Aura	1
3	Completed	Treatment	Balance	1
3	Completed	Treatment	Insomnia	1
3	Completed	Treatment	Insomnia Chronic	5
3	Completed	Treatment	Insomnia / OSAS (Obstructive Sleep Apneas Syndrome)	1
3	Completed	Treatment	Sleep Initiation and Maintenance Disorders	2
3	Completed	Treatment	Transient Insomnia	1
3	Terminated	Treatment	Acute Depressive Episode	1
3	Terminated	Treatment	Asthma / Insomnia	1
3	Terminated	Treatment	Bipolar Disorder (BD)	2
3	Terminated	Treatment	Bipolar Disorder (BD) / Insomnia	1
3	Terminated	Treatment	Insomnia Chronic	1
3	Terminated	Treatment	Insomnia / Major Depressive Disorder (MDD)	1
3	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD) / Insomnia Chronic	1
3	Withdrawn	Treatment	Bipolar Disorder (BD)	1
4	Active Not Recruiting	Treatment	Insomnia Chronic	1
4	Completed	Treatment	ADHD With Sleep Onset Insomnia	1
4	Completed	Treatment	Bipolar Disorder (BD)	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Treatment	Circadian Dysregulation	1
4	Completed	Treatment	Insomnia	2
4	Completed	Treatment	Insomnia Chronic	2
4	Completed	Treatment	Insomnia / Major Depressive Disorder (MDD)	1
4	Completed	Treatment	Insomnia / Quadriplegia / Sleep disorders and disturbances / Spinal Cord Injuries (SCI)	1
4	Completed	Treatment	Liver Cirrhosis	1
4	Completed	Treatment	REM Sleep Behavior Disorder	1
4	Completed	Treatment	Schizoaffective Disorders / Schizophrenic Disorders / Schizophreniform Disorders	1
4	Completed	Treatment	Schizophrenic Disorders	1
4	Completed	Treatment	Seasonal Affective Disorder (SAD)	1
4	Completed	Treatment	Sleep Deprivation	1
4	Not Yet Recruiting	Prevention	Delirium in Old Age	1
4	Recruiting	Prevention	Delirium	1
4	Recruiting	Treatment	Delirium	1
4	Recruiting	Treatment	Insomnia	1
4	Terminated	Treatment	Insomnia Chronic	1
4	Terminated	Treatment	Migraine	1
4	Terminated	Treatment	Parkinson's Disease (PD)	1
4	Unknown Status	Treatment	Brain Injury / Insomnia	1
4	Unknown Status	Treatment	Insomnia	1
4	Withdrawn	Other	Delirium	1
Not Available	Active Not Recruiting	Prevention	Delirium / Sleep Deprivation	1
Not Available	Completed	Not Available	Insomnia	2
Not Available	Completed	Basic Science	Healthy Volunteers	1
Not Available	Completed	Diagnostic	OSAS (Obstructive Sleep Apneas Syndrome)	1
Not Available	Terminated	Treatment	Insomnia / Panic Disorders	1
Not Available	Terminated	Treatment	Pain, Neuropathic	1
Not Available	Terminated	Treatment	Parkinsonism / REM Behavior Disorder	1
Not Available	Withdrawn	Treatment	Circadian Dysregulation / Diffuse Lewy Body Disease / Huntington's Disease (HD) / Parkinson's Disease (PD) / Sleep disorders and disturbances	1

Pharmacoeconomics

Manufacturers

Takeda global research development center inc

Packagers

Bryant Ranch Prepack
DispenseXpress Inc.
Innoviant Pharmacy Inc.
Physicians Total Care Inc.
Rebel Distributors Corp.
Southwood Pharmaceuticals
Takeda Pharmaceutical Co. Ltd.

Dosage forms

Form	Route	Strength
Tablet	Oral	8 mg/1
Tablet, film coated	Oral	8 mg/1

Prices

Unit description	Cost	Unit
Rozerem 8 mg tablet	5.17USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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US6034239	No	2000-03-07	2019-07-22
US10098866	No	2018-10-16	2021-11-16

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	2.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0164 mg/mL	ALOGPS
logP	3.03	ALOGPS
logP	2.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.52 m³·mol^-1	ChemAxon
Polarizability	29.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9934
Caco-2 permeable	+	0.5893
P-glycoprotein substrate	Substrate	0.5211
P-glycoprotein inhibitor I	Non-inhibitor	0.8548
P-glycoprotein inhibitor II	Non-inhibitor	0.7877
Renal organic cation transporter	Non-inhibitor	0.6381
CYP450 2C9 substrate	Non-substrate	0.7876
CYP450 2D6 substrate	Non-substrate	0.6392
CYP450 3A4 substrate	Substrate	0.512
CYP450 1A2 substrate	Inhibitor	0.7314
CYP450 2C9 inhibitor	Non-inhibitor	0.6471
CYP450 2D6 inhibitor	Non-inhibitor	0.5916
CYP450 2C19 inhibitor	Inhibitor	0.8314
CYP450 3A4 inhibitor	Non-inhibitor	0.9196
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.7763
Ames test	Non AMES toxic	0.7016
Carcinogenicity	Non-carcinogens	0.8206
Biodegradation	Ready biodegradable	0.6635
Rat acute toxicity	2.1034 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7898
hERG inhibition (predictor II)	Inhibitor	0.5

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0nmi-2980000000-5ee1e7ec83e5c4578dfe

Taxonomy

Description: This compound belongs to the class of organic compounds known as indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Indanes
Sub Class: Not Available
Direct Parent: Indanes
Alternative Parents: Coumarans / Alkyl aryl ethers / Secondary carboxylic acid amides / Oxacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents: Indane / Coumaran / Alkyl aryl ether / Carboxamide group / Secondary carboxylic acid amide / Oxacycle / Organoheterocyclic compound / Ether / Carboxylic acid derivative / Hydrocarbon derivative
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: Not Available

Targets

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.0138	N/A	N/A	12213063

Details1. Melatonin receptor type 1A

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Multitarget

General Function: Organic cyclic compound binding
Specific Function: High affinity receptor for melatonin. Likely to mediates the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that ...
Gene Name: MTNR1A
Uniprot ID: P48039
Uniprot Name: Melatonin receptor type 1A
Molecular Weight: 39374.315 Da

References

Kato K, Hirai K, Nishiyama K, Uchikawa O, Fukatsu K, Ohkawa S, Kawamata Y, Hinuma S, Miyamoto M: Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist. Neuropharmacology. 2005 Feb;48(2):301-10. [PubMed:15695169]
Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265]
Greenblatt DJ, Harmatz JS, Karim A: Age and gender effects on the pharmacokinetics and pharmacodynamics of ramelteon, a hypnotic agent acting via melatonin receptors MT1 and MT2. J Clin Pharmacol. 2007 Apr;47(4):485-96. [PubMed:17389558]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650]
Miyamoto M: Effect of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist, on motor performance in mice. Neurosci Lett. 2006 Jul 24;402(3):201-4. Epub 2006 May 24. [PubMed:16730121]
Authors unspecified: Ramelteon: TAK 375. Drugs R D. 2005;6(3):186-8. [PubMed:15869323]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178]
Miyamoto M: [A novel therapeutic drug: ramelteon]. Nihon Rinsho. 2009 Aug;67(8):1595-600. [PubMed:19768947]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111]
Johnson MW, Suess PE, Griffiths RR: Ramelteon: a novel hypnotic lacking abuse liability and sedative adverse effects. Arch Gen Psychiatry. 2006 Oct;63(10):1149-57. [PubMed:17015817]
Zammit G, Erman M, Wang-Weigand S, Sainati S, Zhang J, Roth T: Evaluation of the efficacy and safety of ramelteon in subjects with chronic insomnia. J Clin Sleep Med. 2007 Aug 15;3(5):495-504. [PubMed:17803013]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.045	N/A	N/A	12213063

Details2. Melatonin receptor type 1B

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Multitarget

General Function: Melatonin receptor activity
Specific Function: High affinity receptor for melatonin. Likely to mediates the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that ...
Gene Name: MTNR1B
Uniprot ID: P49286
Uniprot Name: Melatonin receptor type 1B
Molecular Weight: 40187.895 Da

References

Kato K, Hirai K, Nishiyama K, Uchikawa O, Fukatsu K, Ohkawa S, Kawamata Y, Hinuma S, Miyamoto M: Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist. Neuropharmacology. 2005 Feb;48(2):301-10. [PubMed:15695169]
Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265]
Greenblatt DJ, Harmatz JS, Karim A: Age and gender effects on the pharmacokinetics and pharmacodynamics of ramelteon, a hypnotic agent acting via melatonin receptors MT1 and MT2. J Clin Pharmacol. 2007 Apr;47(4):485-96. [PubMed:17389558]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650]
Miyamoto M: Effect of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist, on motor performance in mice. Neurosci Lett. 2006 Jul 24;402(3):201-4. Epub 2006 May 24. [PubMed:16730121]
Authors unspecified: Ramelteon: TAK 375. Drugs R D. 2005;6(3):186-8. [PubMed:15869323]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178]
Miyamoto M: [A novel therapeutic drug: ramelteon]. Nihon Rinsho. 2009 Aug;67(8):1595-600. [PubMed:19768947]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111]
Johnson MW, Suess PE, Griffiths RR: Ramelteon: a novel hypnotic lacking abuse liability and sedative adverse effects. Arch Gen Psychiatry. 2006 Oct;63(10):1149-57. [PubMed:17015817]
Zammit G, Erman M, Wang-Weigand S, Sainati S, Zhang J, Roth T: Evaluation of the efficacy and safety of ramelteon in subjects with chronic insomnia. J Clin Sleep Med. 2007 Aug 15;3(5):495-504. [PubMed:17803013]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852]
Neubauer DN: A review of ramelteon in the treatment of sleep disorders. Neuropsychiatr Dis Treat. 2008 Feb;4(1):69-79. [PubMed:18728808]
Ramelteon FDA label [File]

Details2. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852]
Pandi-Perumal SR, Spence DW, Verster JC, Srinivasan V, Brown GM, Cardinali DP, Hardeland R: Pharmacotherapy of insomnia with ramelteon: safety, efficacy and clinical applications. J Cent Nerv Syst Dis. 2011 Apr 12;3:51-65. doi: 10.4137/JCNSD.S1611. Print 2011. [PubMed:23861638]

Details3. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852]

Details4. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 05:39

Ramelteon

Identification

Structure for Ramelteon (DB00980)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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References