MELATONIN

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H16N2O2
Molecular Weight	232.2788
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=NCCc1c[nH]c2ccc(cc12)OC)O

InChI

InChIKey=DRLFMBDRBRZALE-UHFFFAOYSA-N

InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

HIDE SMILES / InChI

Molecular Formula	C13H16N2O2
Molecular Weight	232.2788
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26731279 | https://www.ncbi.nlm.nih.gov/pubmed/19966183 |

Melatonin (5-methoxy N-acetyltryptamine) is a hormone synthesized and released from the pineal gland at night, which acts on specific high affinity G-protein coupled receptors to regulate various aspects of physiology and behaviour, including circadian and seasonal responses, and some retinal, cardiovascular and immunological functions. Melatonin is also made synthetically and available without a prescription as an over-the-counter (OTC) dietary supplement in the U.S. Melatonin supplementation has many uses, however, it has been widely studied for treatment of jet lag and sleep disorders. Parents may consider using melatonin to help their child who has a trouble falling asleep. A medical professional should always evaluate insomnia or other sleeping disorders in children. Additionally, melatonin has been shown to protect against oxidative stress in various, highly divergent experimental systems. There are many reasons for its remarkable protective potential. In mammals, melatonin binds to a number of receptor subtypes including high-affinity (MT1 and MT2) and low-affinity (MT3, nuclear orphan receptors) binding sites, which are distributed throughout the central nervous system and periphery.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Melatonin receptor type 1A 2 Target ID: P48039 Gene ID: 4543.0 Gene Symbol: MTNR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19966183	Agonist 2470
Melatonin receptor type 1B 3 Target ID: P49286 Gene ID: 4544.0 Gene Symbol: MTNR1B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19449447	Agonist 2470

Conditions

Condition	Modality	Targets	Highest Phase	Product
Jet lag syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26731279	Primary		Not Provided 492	Unknown Approved Use Unknown
Insomnia 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28364493	Primary		Phase III 643	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of tamoxifen and melatonin on mammary gland cancer induced by N-methyl-N-nitrosourea and by 7,12-dimethylbenz(a)anthracene, respectively, in female Sprague-Dawley rats.	2001	11232869
The antioxidative potential of melatonin in the skin.	2001	11225196
Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.	2001	11169730
Melatonin's gastroprotective and antistress roles involve both central and peripheral effects.	2001 Feb	11227676
Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study.	2001 Feb	11226744
Effects of bilateral ganglionectomy and melatonin replacement on seasonal rhythm of testicular activity in Zembra Island wild rabbits (Oryctolagus cuniculus).	2001 Feb	11226057
Low ambient temperature accelerates short-day responses in Siberian hamsters by altering responsiveness to melatonin.	2001 Feb	11220782
Effect of exogenous melatonin on vascular reactivity and nitric oxide in postmenopausal women: role of hormone replacement therapy.	2001 Feb	11207642
The influence of 1.2 microT, 60 Hz magnetic fields on melatonin- and tamoxifen-induced inhibition of MCF-7 cell growth.	2001 Feb	11180258
Diurnal and seasonal variations in the duration and depth of the longest dives in southern elephant seals (Mirounga leonina): possible physiological and behavioural constraints.	2001 Feb	11171347
Photoperiodic regulation of prolactin gene expression in the Syrian hamster by a pars tuberalis-derived factor.	2001 Feb	11168840
The critical stage of pinealectomy surgery after which scoliosis is produced in young chickens.	2001 Feb 1	11224858
Pineal modulation of thymus and immune function in a seasonally breeding tropical rodent, Funambulus pennanti.	2001 Feb 1	11169496
Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats.	2001 Feb 1	11165868
Human melatonin suppression by light: a case for scotopic efficiency.	2001 Feb 16	11166934
Melatonin secretion after surgery.	2001 Feb 17	11229697
Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken.	2001 Feb 2	11163293
An hPer2 phosphorylation site mutation in familial advanced sleep phase syndrome.	2001 Feb 9	11232563
Melatonin in medically ill patients with insomnia: a double-blind, placebo-controlled study.	2001 Jan	11235927
Interaction between the adrenal and the pineal gland in chronic experimental inflammation induced by BCG in mice.	2001 Jan	11235023
[Melatonin: is there a rationale for the clinical use of this hormone in sleep therapy?].	2001 Jan	11233494
[Drug for the treatment of sleep disorders--review].	2001 Jan	11233487
Human melatonin regulation is not mediated by the three cone photopic visual system.	2001 Jan	11232036
Transition from dim to bright light in the morning induces an immediate elevation of cortisol levels.	2001 Jan	11231993
Diminished melatonin secretion in the elderly caused by insufficient environmental illumination.	2001 Jan	11231989
Circadian phase resetting in older people by ocular bright light exposure.	2001 Jan	11217145
Superior cervical ganglionectomy leads to dampening of amplitude of temperature rhythm in rats.	2001 Jan	11211561
Bright light therapy and melatonin in motor restless behaviour in dementia: a placebo-controlled study.	2001 Jan	11180494
A test of the coincidence and duration models of melatonin action in Siberian hamsters. II. The effects of 4- and 8-hr melatonin infusions on testicular development of pinealectomized juvenile Siberian hamsters (Phodopus sungorus).	2001 Jan	11168908
Lack of changes in serum prolactin, FSH, TSH, and estradiol after melatonin treatment in doses that improve sleep and reduce benzodiazepine consumption in sleep-disturbed, middle-aged, and elderly patients.	2001 Jan	11168905
Melatonin reduces dinitrobenzene sulfonic acid-induced colitis.	2001 Jan	11168901
Inhibition of androgen-sensitive LNCaP prostate cancer growth in vivo by melatonin: association of antiproliferative action of the pineal hormone with mt1 receptor protein expression.	2001 Jan 1	11170132
Direct separation of the stereoisomers of methoxytetrahydronaphthalene derivatives, new agonist and antagonist ligands for melatonin receptors, by liquid chromatography on cellulose chiral stationary phases.	2001 Jan 12	11217017
Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice.	2001 Jan 12	11213364
Effects by doxorubicin on the myocardium are mediated by oxygen free radicals.	2001 Jan 12	11213359
Effect of melatonin on circadian rhythm, locomotor activity and body temperature in the intact house sparrow, Japanese quail and owl.	2001 Jan 19	11166707
Melatonin inhibits Arg-vasopressin release via MT(2) receptor in the suprachiasmatic nucleus-slice culture of rats.	2001 Jan 19	11166706
Effects of vehicles and enhancers on transdermal delivery of melatonin.	2001 Jan 5	11165821
The effect of short intermittent light exposures on the melatonin circadian rhythm and NMU-induced breast cancer in female F344/N rats.	2001 Jan-Feb	11215676
A randomized, double-blind, placebo-controlled crossover study of the effect of exogenous melatonin on delayed sleep phase syndrome.	2001 Jan-Feb	11211063
Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men.	2001 Mar	11238497
Circadian rhythms of women with fibromyalgia.	2001 Mar	11238482
The immunotherapeutic potential of melatonin.	2001 Mar	11227046
Effect of melatonin on oxidative status of rat brain, liver and kidney tissues under constant light exposure.	2001 Mar	11223869
Multiple binding sites for melatonin on Kv1.3.	2001 Mar	11222291
Photoresponsive Fischer 344 Rats are reproductively inhibited by melatonin and differ in 2-[125I] lodomelatonin binding from nonphotoresponsive Sprague-Dawley rats.	2001 Mar	11207936
Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells.	2001 Mar 15	11222942
Dual effects of melatonin on barbiturate-induced narcosis in rats.	2001 Mar 16	11226639
Tissue-specific abolition of Per1 expression in the pars tuberalis by pinealectomy in the Syrian hamster.	2001 Mar 5	11234767
Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells.	2001 Mar-Apr	11229798

Patents

Sample Use Guides

In Vivo Use Guide

Fast Release Melatonin (FR MLT): 3mg capsules of melatonin will be used. The dose of FR MLT will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily. Drug: Timed Release Melatonin (TR MLT): 3 mg capsules will be used. The dose of TR MLT will be will be 3 mg for children less than or equal to 20 kg, and 6 mg for children greater than 20 kg. The study medication will be given one hour before bedtime, once daily.

Route of Administration: Oral

In Vitro Use Guide

It was observed that 10-7 M melatonin was considered an optimum concentration and significantly promoted the in vitro development of murine microinjected pronuclear embryos, as indicated by the increased blastocyst rate, hatching blastocyst rate and blastocyst cell number. When these blastocysts were implanted into recipient mice, the pregnancy rate and birth rate were significantly higher than those of the microinjected control, respectively. Mechanistic studies revealed that melatonin treatment reduced reactive oxygen species (ROS) production and cellular apoptosis during in vitro embryo development and improved the quality of the blastocysts. The implantation of quality-improved blastocysts led to elevated pregnancy and birth rates. In conclusion, the results revealed that the anti-oxidative and anti-apoptotic activities of melatonin improved the quality of microinjected pronuclear embryos and subsequently increased both the efficiency of embryo implantation and the birth rate of the pups. Therefore, the melatonin supplementation may provide a novel alternative method for generating large numbers of transgenic mice and this method can probably be used in human-assisted reproduction and genome editing.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:29:56 UTC 2021` Edited by `admin` on `Fri Jun 25 21:29:56 UTC 2021`
Record UNII	JL5DK93RCL
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MELATONIN

Official Name

English

MELATONIN [EMA EPAR]

Common Name

English

ACETAMIDE, N-(2-(5-METHOXYINDOL-3-YL)ETHYL)-

Systematic Name

English

REGULIN

Brand Name

English

MELATONIN [USP-RS]

Common Name

English

MELATONIN [INCI]

Common Name

English

MELATONIN [WHO-DD]

Common Name

English

MELATONINE

Common Name

English

NSC-113928

Code

English

MELATONIN [HSDB]

Common Name

English

MELATONIN [DSC]

Common Name

English

BCI-049

Code

English

MELATONIN [MI]

Common Name

English

MELATONIN [GREEN BOOK]

Common Name

English

J5.258B

Code

English

ACETAMIDE, N-(2-(5-METHOXY-1H-INDOL-3-YL)ETHYL)-

Systematic Name

English

MELATOL

Brand Name

English

MELOVINE

Brand Name

English

NSC-56423

Code

English

CIRCADIN

Brand Name

English

5-METHOXY N-ACETYL-TRYPTAMINE

Common Name

English

MELATONIN [MART.]

Common Name

English

MELATONIN [VANDF]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

melatonin