MELATONIN

US Unapproved Medicine

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

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 2456
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 2456

Conditions

Condition	Modality	Targets	Highest Phase	Product
Jet lag syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26731279	Primary		Not Provided 523	Unknown Approved Use Unknown
Insomnia 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28364493	Primary		Phase III 650	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ultrastructural confirmation of neuronal protection by melatonin against the neurotoxin 6-hydroxydopamine cell damage.	1999 Feb 13	10082807
Aspects of melatonin manufacturing and requirements for a reliable active component.	1999 Jan-Apr	10085477
Ototoxicity caused by aminoglycosides is ameliorated by melatonin without interfering with the antibiotic capacity of the drugs.	2000 Jan	10626598
Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors.	2000 Mar	10696085
Melatonin suppresses iron-induced neurodegeneration in rat brain.	2000 Mar 15	10802221
Role of heme oxygenase-1 in the regulation of manganese superoxide dismutase gene expression in oxidatively-challenged astroglia.	2000 Oct	10942521
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
Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study.	2001 Feb	11226744
Effects of aging on the intrinsic circadian period of totally blind humans.	2001 Feb	11220783
Chronic exposure to ELF magnetic fields during night sleep with electric sheet: effects on diurnal melatonin rhythms in men.	2001 Feb	11180260
The influence of 1.2 microT, 60 Hz magnetic fields on melatonin- and tamoxifen-induced inhibition of MCF-7 cell growth.	2001 Feb	11180258
The influence of long-term exposure of mice to randomly varied power frequency magnetic fields on their nocturnal melatonin secretion patterns.	2001 Feb	11161661
Circadian regulation of phospholipid metabolism in retinal photoreceptors and ganglion cells.	2001 Feb	11158255
Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity.	2001 Feb	11158039
Pineal modulation of thymus and immune function in a seasonally breeding tropical rodent, Funambulus pennanti.	2001 Feb 1	11169496
Rhythms of the pineal N-acetyltransferase mRNA and melatonin concentrations during embryonic and post-embryonic development in chicken.	2001 Feb 2	11163293
Risk of breast cancer among Norwegian women with visual impairment.	2001 Feb 2	11161406
[Melatonin: is there a rationale for the clinical use of this hormone in sleep therapy?].	2001 Jan	11233494
Human melatonin regulation is not mediated by the three cone photopic visual system.	2001 Jan	11232036
Circadian phase resetting in older people by ocular bright light exposure.	2001 Jan	11217145
Bright light therapy and melatonin in motor restless behaviour in dementia: a placebo-controlled study.	2001 Jan	11180494
Absolute configuration of N-[(-)-2-(7-methoxy-1,2,3,3-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide, a highly potent and selective melatonin analogue.	2001 Jan	11173413
Seasonal alterations in circadian melatonin rhythms of the European wild boar and domestic gilt.	2001 Jan	11168906
Changes of serum melatonin level and its relationship to feto-placental unit during pregnancy.	2001 Jan	11168904
Melatonin protects against 6-OHDA-induced neurotoxicity in rats: a role for mitochondrial complex I activity.	2001 Jan	11149904
Melatonin production in healthy infants: evidence for seasonal variations.	2001 Jan	11134493
Vitamin D resistance in RAS-transformed keratinocytes: mechanism and reversal strategies.	2001 Jan	11121228
Circadian variation in O6-alkylguanine-DNA alkyltransferase activity in circulating blood mononuclear cells of healthy human subjects.	2001 Jan 1	11149421
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
Melatonin counteracts potentiation by homocysteine of KCL-induced vasoconstriction in human umbilical artery: relation to calcium influx.	2001 Jan 26	11162615
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
Disruption of the nocturnal testosterone rhythm by sleep fragmentation in normal men.	2001 Mar	11238497
Circadian rhythms of women with fibromyalgia.	2001 Mar	11238482
Effect of melatonin on oxidative status of rat brain, liver and kidney tissues under constant light exposure.	2001 Mar	11223869
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.	2001 Mar	11181495

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.

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