Melatonin

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'''Pubchem(896)'''
 
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'''Chembank(988)'''
 
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A biogenic amine that is found in animals and plants. In mammals, melatonin is produced by the PINEAL GLAND. Its secretion increases in darkness and decreases during exposure to light. Melatonin is implicated in the regulation of SLEEP, mood, and REPRODUCTION. Melatonin is also an effective antioxidant.
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==Description==
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A biogenic amine that is found in animals and plants. In mammals,   melatonin is produced by the PINEAL GLAND. Its secretion increases in   darkness and decreases during exposure to light. Melatonin is   implicated in the regulation of SLEEP, mood, and REPRODUCTION.   Melatonin is also an effective antioxidant.
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==General Properties==
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Therapeutic Indications
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<b>*Molecular Weight</b>
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*Neoplasms 1516565
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Therapeutic Uses
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232.28
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*anti-neoplastic 1516565
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NEXT BIO Database
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<b>*Molecular Formula</b>
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'''Drug Type:''' Small Molecule; Approved
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C<sub>1</sub><sub>3</sub>H<sub>1</sub><sub>6</sub>N<sub>2</sub>O<sub>2</sub>
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'''Pharmacology:''' Melatonin is a hormone normally produced in the pineal gland and released into the blood. The essential amino acid L-tryptophan is a precursor in the synthesis of melatonin. It helps regulate sleep-wake cycles or the circadian rhythm. Production of melatonin is stimulated by darkness and inhibited by light. High levels of melatonin induce sleep and so consumption of the drug can be used to combat insomnia and jet lag.
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<b>*IUPAC NAME</b>
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'''Mechanism of Action:''' Melatonin is a derivative of tryptophan. It binds to melatonin receptor type 1A, which then acts on adenylate cylcase and the inhibition of a cAMP signal transduction pathway. Melatonin not only inhibits adenylate cyclase, but it also activates phosphilpase C. This potentiates the release of arachidonate.
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N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
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'''Indication:''' For the treatment of insomnia and jet lag
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<b>*Canonical Smiles</b>
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'''Half Life:''' 35 to 50 minutes
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'''NASID DATABASE'''
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CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC
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Lipinski’s “Rule of Five” Prediction for a Compound’s ABSORPTION OR PERMEABILITY PROPERTIES
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{| border="1;width:100%; height:200px;style=text-align:center"
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-
|+'''Table I:'''
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|-
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! style="background:brown; color:white" |4
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! style="background:brown; color:white" |3
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! style="background:brown; color:white" |2
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! style="background:brown; color:white" |1
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-
! style="background:brown; color:white" |0
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|-
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|GOOD
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|INDETERMINATE
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|INDETERMINATE
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|INDETERMINATE
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|POOR
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-
|-
+
-
|}
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KEGG Pathway(C01598)
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*Tryptophan metabolism
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*Neuroactive ligand-receptor interaction
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{| border="1;width:100%; height:200px;style=text-align:center"
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<b>*Isomeric Smiles</b>
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|+'''Table I:'''
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|-
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! style="background:brown; color:white" |MMDB ID
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! style="background:brown; color:white" |PDB ID
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! style="background:brown; color:white" |Reference
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==PhysioChemical Properties==
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|-
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|64112
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<b>*Melting Point</b>
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|2QWX
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|Reference: Calamini B, Santarsiero BD, Boutin JA, Mesecar ADKinetic, thermodynamic and X-ray structural insights into the interaction of melatonin and analogues with quinone reductase 2Biochem. J. v413, p.81-91
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117(EXP)
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|-
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|66545
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<b>*LogP</b>
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|2QX4
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|Reference: Calamini B, Santarsiero BD, Boutin JA, Mesecar ADKinetic, thermodynamic and X-ray structural insights into the interaction of melatonin and analogues with quinone reductase 2Biochem. J. v413, p.81-91
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1.65(EST)
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|-
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|66546
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<b>*Water Solubility</b>
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|2QX6
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|Reference: Calamini B, Santarsiero BD, Boutin JA, Mesecar ADKinetic, thermodynamic and X-ray structural insights into the interaction of melatonin and analogues with quinone reductase 2Biochem. J. v413, p.81-91
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|-
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|}
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==External Links==
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{| border="1;width:100%; height:200px;style=text-align:center"
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=896]Pubchem
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|+'''Table I:'''
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*[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=2QWX]]2QWX,[[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=2QX4]]2QX4,[[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=2QX6]]2QX6,
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|-
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C01598]KEGG Compound
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! style="background:brown; color:white" |Physical Property
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*[http://www.hmdb.ca/metabolites/HMDB01389]Human Metabolome DataBase
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! style="background:brown; color:white" |Value
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*[http://www.drugbank.ca/drugs/DB01065]Drugbank
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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[[Categories:Hormones]]
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! style="background:brown; color:white" |Source
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|-
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|Melting Point  
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|117
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|deg C
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|
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|EXP
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|-
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|log P (octanol-water)
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|1.650
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|(none)
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|
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|EST
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|-
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|Atmospheric OH Rate Constant
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|2.12E-10
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|cm3/molecule-sec
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|25
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|EST
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|-
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|}
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Table I:'''
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|-
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! style="background:brown; color:white" |Organism
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! style="background:brown; color:white" |Test Type 
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! style="background:brown; color:white" |Route 
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! style="background:brown; color:white" |Reported Dose (Normalized Dose)
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! style="background:brown; color:white" |Source
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|-
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|mouse
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|LD50
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|intraperitoneal
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|1375mg/kg (1375mg/kg)
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|Pharmaceutical Chemistry Journal Vol. 17, Pg. 559, 1983.
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|-
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|mouse
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|LD50
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|intravenous
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|180mg/kg (180mg/kg)
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|U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02739.
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|-
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|mouse
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|LD50
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|oral
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|1250mg/kg (1250mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
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|-
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|mouse
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|LD50
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|subcutaneous
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|1600mg/kg (1600mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
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|-
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|rat
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|LD50
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|intraperitoneal
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|1131mg/kg (1131mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
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|-
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|rat
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|LD50
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|intravenous
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|356mg/kg (356mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
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-
|-
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|rat
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|LD50
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|oral
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|3200mg/kg (3200mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
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-
|-
+
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|rat
+
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|LD50
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|subcutaneous
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|1600mg/kg (1600mg/kg)
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|Journal of Pharmacology and Experimental Therapeutics. Vol. 227, Pg. 587, 1983.Link to PubMed
+
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|-
+
-
|}
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Revision as of 00:00, 15 January 2001


Contents

Description

A biogenic amine that is found in animals and plants. In mammals, melatonin is produced by the PINEAL GLAND. Its secretion increases in darkness and decreases during exposure to light. Melatonin is implicated in the regulation of SLEEP, mood, and REPRODUCTION. Melatonin is also an effective antioxidant.

General Properties

*Molecular Weight

232.28

*Molecular Formula

C13H16N2O2

*IUPAC NAME

N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

*Canonical Smiles

CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC

*Isomeric Smiles



PhysioChemical Properties

*Melting Point

117(EXP)

*LogP

1.65(EST)

*Water Solubility


External Links

Categories:Hormones

Retrieved from "http://277988.efsst.group/drugpedia/index.php/Melatonin"