Melatonin

Identification

Summary

Melatonin is an endogenous hormone produced by the pineal gland that regulates sleep-wake cycles and when provided exogenously has beneficial effects on sleep-onset latency; available as an over-the-counter supplement.

Brand Names
Circadin
Generic Name
Melatonin
DrugBank Accession Number
DB01065
Background

Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B. Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and lowering the body temperature. Melatonin is also implicated in the regulation of mood, learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders (ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.

Type
Small Molecule
Groups
Approved, Nutraceutical, Vet approved
Structure
Weight
Average: 232.2783
Monoisotopic: 232.121177766
Chemical Formula
C13H16N2O2
Synonyms
  • 5-methoxy-N-acetyltryptamine
  • Melatonin
  • Melatonina
  • Mélatonine
  • N-[2-(5-methoxyindol-3-yl)ethyl]acetamide
  • N-Acetyl-5-methoxytryptamine
External IDs
  • BCI-049
  • J5.258B
  • NPC-15
  • NSC-113928
  • NSC-56423

Pharmacology

Indication

Used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. Evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. It has received FDA orphan drug status as an oral medication for this use. A number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. It appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. It may also improve secondary insomnia associated with various sleep-wake cycle disturbances. Other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (DSPS), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with IL-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofInsomnia••••••••••••
Used in combination to manageInsomniaCombination Product in combination with: Valerian (DB13196), gamma-Aminobutyric acid (DB02530)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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. MT1 and MT2 receptors may be a target for the treatment of circadian and non circadian sleep disorders because of their differences in pharmacology and function within the SCN. SCN is responsible for maintaining the 24 hour cycle which regulates many different body functions ranging from sleep to immune functions

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. By binding to melatonin receptors 1 and 2, the downstream signallling cascades have various effects in the body. The melatonin receptors are G protein-coupled receptors and are expressed in various tissues of the body. There are two subtypes of the receptor in humans, melatonin receptor 1 (MT1) and melatonin receptor 2 (MT2). Melatonin and melatonin receptor agonists, on market or in clinical trials, all bind to and activate both receptor types.The binding of the agonists to the receptors has been investigated for over two decades or since 1986. It is somewhat known, but still not fully understood. When melatonin receptor agonists bind to and activate their receptors it causes numerous physiological processes. MT1 receptors are expressed in many regions of the central nervous system (CNS): suprachiasmatic nucleus of the hypothalamus (SNC), hippocampus, substantia nigra, cerebellum, central dopaminergic pathways, ventral tegmental area and nucleus accumbens. MT1 is also expressed in the retina, ovary, testis, mammary gland, coronary circulation and aorta, gallbladder, liver, kidney, skin and the immune system. MT2 receptors are expressed mainly in the CNS, also in the lung, cardiac, coronary and aortic tissue, myometrium and granulosa cells, immune cells, duodenum and adipocytes. The binding of melatonin to melatonin receptors activates a few signaling pathways. MT1 receptor activation inhibits the adenylyl cyclase and its inhibition causes a rippling effect of non activation; starting with decreasing formation of cyclic adenosine monophosphate (cAMP), and then progressing to less protein kinase A (PKA) activity, which in turn hinders the phosphorilation of cAMP responsive element-binding protein (CREB binding protein) into P-CREB. MT1 receptors also activate phospholipase C (PLC), affect ion channels and regulate ion flux inside the cell. The binding of melatonin to MT2 receptors inhibits adenylyl cyclase which decreases the formation of cAMP.[4] As well it hinders guanylyl cyclase and therefore the forming of cyclic guanosine monophosphate (cGMP). Binding to MT2 receptors probably affects PLC which increases protein kinase C (PKC) activity. Activation of the receptor can lead to ion flux inside the cell.

TargetActionsOrganism
AMelatonin receptor type 1A
agonist
Humans
AMelatonin receptor type 1B
agonist
Humans
UEstrogen receptor alpha
antagonist
Humans
UNuclear receptor ROR-beta
agonist
Humans
UCalmodulinNot AvailableHumans
UMyeloperoxidase
inhibitor
Humans
UEosinophil peroxidase
inhibitor
Humans
UCalreticulinNot AvailableHumans
UAcetylserotonin O-methyltransferaseNot AvailableHumans
URibosyldihydronicotinamide dehydrogenase [quinone]Not AvailableHumans
Absorption

The absorption and bioavailability of melatonin varies widely.

Volume of distribution

Not Available

Protein binding

n/a

Metabolism

Hepatically metabolized to at least 14 identified metabolites (identified in mouse urine): 6-hydroxymelatonin glucuronide, 6-hydroxymelatonin sulfate, N-acetylserotonin glucuronide, N-acetylserotonin sulfate, 6-hydroxymelatonin, 2-oxomelatonin, 3-hydroxymelatonin, melatonin glucuronide, cyclic melatonin, cyclic N-acetylserotonin glucuronide, cyclic 6-hydroxymelatonin, 5-hydroxyindole-3-acetaldehyde, di-hydroxymelatonin and its glucuronide conjugate. 6-Hydroxymelatonin glucuronide is the major metabolite found in mouse urine (65-88% of total melatonin metabolites in urine).

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Route of elimination

Not Available

Half-life

35 to 50 minutes

Clearance

Not Available

Adverse Effects
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Toxicity

Generally well-tolerated when taken orally. The most common side effects, day-time drowsiness, headache and dizziness, appear to occur at the same frequency as with placebo. Other reported side effects include transient depressive symptoms, mild tremor, mild anxiety, abdominal cramps, irritability, reduced alertness, confusion, nausea, vomiting, and hypotension. Safety in Adults: Evidence indicates that it is likely safe to use in oral and parenteral forms for up to two months when used appropriately. Some evidence indicates that it can be safely used orally for up to 9 months in some patients. It is also likely safe to use topically when used appropriately. Safety in Children: Melatonin appeared to be used safely in small numbers of children enrolled in short-term clinical trials. However, concerns regarding safety in children have arisen based on their developmental state. Compared to adults over 20 years of age, people under 20 produce high levels of melatonin. Melatonin levels are inversely related to gonadal development and it is thought that exogenous administration of melatonin may adversely affect gonadal development. Safety during Pregnancy: High doses of melatonin administered orally or parenterally may inhibit ovulation. Not advised for use in individuals who are pregnant or trying to become pregnant. Safety during Lactation: Not recommended as safety has not be established.

Oral, rat: LD50 ≥3200 mg/kg

Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Melatonin is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Melatonin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Melatonin can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Melatonin can be increased when it is combined with Abiraterone.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Melatonin.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may reduce the effects of melatonin.
  • Take after a meal. Administration of melatonin after eating slows the absorption and reduces the Cmax of melatonin.

Products

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International/Other Brands
Mela-T (Alacer Corp. (Canada)) / Melatol (Elisium (Argentina)) / Melatonin (Biomed International Products Corp., Nutravite Pharmaceuticals (2008) Inc., Viva Pharmaceutical Inc., Kripps Pharmacy Ltd., SunOpta Inc.) / Nature'S Harmony (SunOpta Inc. (Canada)) / Revital Melatonin (Chin Tai Ginseng Co., Ltd (Canada)) / Rx Balance (SunOpta Inc. (Canada)) / Sleep Right (SunOpta Inc. (Canada)) / Vivitas (SunOpta Inc. (Canada))
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Sarl2016-09-08Not applicableEU flag
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Sarl2016-09-08Not applicableEU flag
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Sarl2016-09-08Not applicableEU flag
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Sarl2016-09-08Not applicableEU flag
Melatonin NeurimTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Sarl2023-02-08Not applicableEU flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Essential OilOil2.5 mg/10mLCutaneousShantou Youjia E-Commerce Co., Ltd.2024-02-012024-12-31US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Medi-doze Rx Sleep AidMelatonin (6 mg/1) + Valerian (50 mg/1) + gamma-Aminobutyric acid (30 mg/1)TabletOralTwo Hip Consulting, Llc2013-02-202016-04-11US flag

Categories

ATC Codes
N05CH01 — Melatonin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Anisoles / Alkyl aryl ethers / Substituted pyrroles / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
3-alkylindole / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Ether / Heteroaromatic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
acetamides, tryptamines (CHEBI:16796) / Indole alkaloids, Melatonin (C01598) / a small molecule (N-ACETYL-5-METHOXY-TRYPTAMINE)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
JL5DK93RCL
CAS number
73-31-4
InChI Key
DRLFMBDRBRZALE-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
SMILES
COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

References

Synthesis Reference

Robert A. S. Welch, Keith Betteridge, "Method of stimulating cashmere growth on cashmere-producing goats using melatonin." U.S. Patent US4855313, issued August, 1986.

US4855313
General References
  1. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [Article]
  2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [Article]
  3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [Article]
  4. Hattori A, Migitaka H, Iigo M, Itoh M, Yamamoto K, Ohtani-Kaneko R, Hara M, Suzuki T, Reiter RJ: Identification of melatonin in plants and its effects on plasma melatonin levels and binding to melatonin receptors in vertebrates. Biochem Mol Biol Int. 1995 Mar;35(3):627-34. [Article]
  5. Ma X, Chen C, Krausz KW, Idle JR, Gonzalez FJ: A metabolomic perspective of melatonin metabolism in the mouse. Endocrinology. 2008 Apr;149(4):1869-79. doi: 10.1210/en.2007-1412. Epub 2008 Jan 10. [Article]
  6. Reiter RJ, Acuna-Castroviejo D, Tan DX, Burkhardt S: Free radical-mediated molecular damage. Mechanisms for the protective actions of melatonin in the central nervous system. Ann N Y Acad Sci. 2001 Jun;939:200-15. [Article]
Human Metabolome Database
HMDB0001389
KEGG Drug
D08170
KEGG Compound
C01598
PubChem Compound
896
PubChem Substance
46509101
ChemSpider
872
BindingDB
9019
RxNav
6711
ChEBI
16796
ChEMBL
CHEMBL45
ZINC
ZINC000000057060
Therapeutic Targets Database
DAP000429
PharmGKB
PA164752558
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ML1
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Melatonin
PDB Entries
2qwx / 2qx4 / 2qx6 / 4qog / 4qoi / 5i8f / 5mxb / 5mxw / 6tr5
MSDS
Download (72 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailablePostural Instability1
4CompletedOtherPost-operative Pain Management1
4CompletedPreventionAgitation1
4CompletedPreventionFebrile Convulsions1
4CompletedPreventionHuman Endotoxaemia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Mason Distributors
  • Medisca Inc.
  • National Vitamin Company
  • Physiologics
  • Rugby Laboratories
Dosage Forms
FormRouteStrength
Tablet, chewableOral2.5 mg/1
Tablet, extended releaseOral2 mg
CapsuleOral5.00000 mg
OilCutaneous2.5 mg/10mL
TabletOral
LiquidOral1 mg/4mL
TabletNot applicable10 mg/1
CapsuleNot applicable10 mg/1
Capsule, coatedOral3 mg
Capsule, liquid filledOral3 mg
TabletOral3 MG
TabletOral5 MG
Tablet0.5 mg
Tablet1 mg
Tablet2 mg
Tablet3 mg
Tablet4 mg
Tablet5 mg
TabletOral1.500 mg
TabletOral3 mg/1
Tablet, extended releaseOral1 MG
Tablet, extended releaseOral5 MG
TabletSublingual3.000 mg
SolutionOral1 mg/ml
Prices
Unit descriptionCostUnit
Melatonin powder45.6USD g
Melatonin 3 mg tablet0.22USD tablet
Melatonin 5 mg tablet0.12USD tablet
Melatonin 5 mg tablet sl0.1USD tablet
Melatonin sublingual tablet0.09USD tablet
Melatonin 1 mg tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)117 °CPhysProp
logP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP1.42ALOGPS
logP1.15Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.8Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area54.12 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity66.28 m3·mol-1Chemaxon
Polarizability25.65 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9928
Caco-2 permeable-0.5536
P-glycoprotein substrateSubstrate0.6188
P-glycoprotein inhibitor INon-inhibitor0.9569
P-glycoprotein inhibitor IINon-inhibitor0.6838
Renal organic cation transporterNon-inhibitor0.542
CYP450 2C9 substrateNon-substrate0.8231
CYP450 2D6 substrateSubstrate0.5062
CYP450 3A4 substrateSubstrate0.6505
CYP450 1A2 substrateInhibitor0.9304
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8084
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.7194
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6803
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9498
BiodegradationNot ready biodegradable0.8764
Rat acute toxicity1.8922 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9631
hERG inhibition (predictor II)Non-inhibitor0.5124
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-001i-0490000000-aa93967315af900a76ce
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-03k9-0900000000-a15ee6def3f8d75b1231
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-001j-0490000000-94ef1be9ab930060778a
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001i-1490000000-03e24298c7bd1ed4066a
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0076-4920000000-a8d9d614e9f8769a1359
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-1490000000-03e24298c7bd1ed4066a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-001j-0590000000-63d5e32dd5f7877a4402
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-001i-0590000000-52b3a733f8b49582d3fb
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0229-1900000000-d81c6f617bc486066136
Mass Spectrum (Electron Ionization)MSsplash10-03k9-1900000000-45ee4fdc7acdb33dad3b
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-00di-0920000000-f90ec9b77e1a245e35a8
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05fr-0900000000-49e4482c65e82ac64b66
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-003r-0900000000-8a4ae0fd610cca992d74
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0159-0090000000-939a1caf5760c0ba189c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-0930000000-9e6fcea2c634ac9d85a0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-0900000000-ddd29e731a7de56c1808
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-0900000000-34b4fb52810a15ea5bd6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0090000000-5ca2df63ec2baefdae8c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-0190000000-5bae6e63e9b40e60e0a4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-0900000000-529bf6d5c2091993f865
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-0900000000-158a60fe696120b23b41
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a5c-0900000000-5e86b2de659ce47762c0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001i-0900000000-881c0d57239d56c46f2d
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-0910000000-f256f78adbcbeb2464de
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0a4i-0900000000-bd15d952a2fc6c5cbb23
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-05fr-0900000000-7acf9405f4beeb34566c
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-00di-0900000000-13245183cd8c8cd511c3
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-05ai-2900000000-07b3d32f002dba733c10
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0159-0090000000-939a1caf5760c0ba189c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0930000000-9e6fcea2c634ac9d85a0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0900000000-ddd29e731a7de56c1808
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0900000000-34b4fb52810a15ea5bd6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0090000000-5ca2df63ec2baefdae8c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00lr-0090000000-3c42f6997539afb44682
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014m-0960000000-7991e64dacb3c7f5cf32
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-882be43bc196e928a3cf
MS/MS Spectrum - , negativeLC-MS/MSsplash10-014i-0190000000-ddda9232f0e8e1b402f7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0190000000-5bae6e63e9b40e60e0a4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-529bf6d5c2091993f865
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-158a60fe696120b23b41
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a5c-0900000000-5e86b2de659ce47762c0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-881c0d57239d56c46f2d
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0910000000-d659c749adcab685e8bb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-6817d8039761a9058337
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-349d5a97e2406d0db910
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-9e30dcf47c9eca14650e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-1900000000-73dc69b26b1fba60f253
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05ai-2900000000-07b3d32f002dba733c10
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0900000000-2e847095e37f4ffe7c8b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-0960000000-9acd48062f28a100f9da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-5790000000-571ee430d2b0391822e3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-1a38178248f05cf91e65
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-9950a9dee5e36e935714
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0900000000-5d47768c1bb474f51f38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-4900000000-9374ee5bf5eb87317f56
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-159.6858961
predicted
DarkChem Lite v0.1.0
[M-H]-152.8346632
predicted
DarkChem Standard v0.1.0
[M-H]-152.9149983
predicted
DarkChem Lite v0.1.0
[M-H]-165.2831961
predicted
DarkChem Lite v0.1.0
[M-H]-159.7026961
predicted
DarkChem Lite v0.1.0
[M-H]-150.02837
predicted
DeepCCS 1.0 (2019)
[M+H]+159.1911961
predicted
DarkChem Lite v0.1.0
[M+H]+157.166152
predicted
DarkChem Standard v0.1.0
[M+H]+157.1763686
predicted
DarkChem Lite v0.1.0
[M+H]+166.2821961
predicted
DarkChem Lite v0.1.0
[M+H]+159.7927961
predicted
DarkChem Lite v0.1.0
[M+H]+152.38637
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.6747961
predicted
DarkChem Lite v0.1.0
[M+Na]+165.6858961
predicted
DarkChem Lite v0.1.0
[M+Na]+167.0242025
predicted
DarkChem Lite v0.1.0
[M+Na]+165.6891961
predicted
DarkChem Lite v0.1.0
[M+Na]+159.5635961
predicted
DarkChem Lite v0.1.0
[M+Na]+158.4795
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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
  1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [Article]
  4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [Article]
  5. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. [Article]
  6. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. [Article]
  7. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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
  1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [Article]
  2. Boutin JA, Audinot V, Ferry G, Delagrange P: Molecular tools to study melatonin pathways and actions. Trends Pharmacol Sci. 2005 Aug;26(8):412-9. [Article]
  3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [Article]
  4. Srinivasan V, Singh J, Pandi-Perumal SR, Brown GM, Spence DW, Cardinali DP: Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs. Adv Ther. 2010 Nov;27(11):796-813. doi: 10.1007/s12325-010-0065-y. Epub 2010 Sep 6. [Article]
  5. Carocci A, Catalano A, Lovece A, Lentini G, Duranti A, Lucini V, Pannacci M, Scaglione F, Franchini C: Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors. Bioorg Med Chem. 2010 Sep 1;18(17):6496-511. doi: 10.1016/j.bmc.2010.06.100. Epub 2010 Jul 3. [Article]
  6. Prendergast BJ: MT1 melatonin receptors mediate somatic, behavioral, and reproductive neuroendocrine responses to photoperiod and melatonin in Siberian hamsters (Phodopus sungorus). Endocrinology. 2010 Feb;151(2):714-21. doi: 10.1210/en.2009-0710. Epub 2009 Dec 4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [Article]
  2. Yoo YM, Jeung EB: Melatonin-induced estrogen receptor alpha-mediated calbindin-D9k expression plays a role in H2O2-mediated cell death in rat pituitary GH3 cells. J Pineal Res. 2009 Nov;47(4):301-7. doi: 10.1111/j.1600-079X.2009.00714.x. Epub 2009 Oct 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsi...
Gene Name
RORB
Uniprot ID
Q92753
Uniprot Name
Nuclear receptor ROR-beta
Molecular Weight
53219.385 Da
References
  1. Becker-Andre M, Wiesenberg I, Schaeren-Wiemers N, Andre E, Missbach M, Saurat JH, Carlberg C: Pineal gland hormone melatonin binds and activates an orphan of the nuclear receptor superfamily. J Biol Chem. 1994 Nov 18;269(46):28531-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
References
  1. del Rio B, Garcia Pedrero JM, Martinez-Campa C, Zuazua P, Lazo PS, Ramos S: Melatonin, an endogenous-specific inhibitor of estrogen receptor alpha via calmodulin. J Biol Chem. 2004 Sep 10;279(37):38294-302. Epub 2004 Jun 30. [Article]
  2. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Galijasevic S, Abdulhamid I, Abu-Soud HM: Melatonin is a potent inhibitor for myeloperoxidase. Biochemistry. 2008 Feb 26;47(8):2668-77. doi: 10.1021/bi702016q. Epub 2008 Feb 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmen...
Gene Name
EPX
Uniprot ID
P11678
Uniprot Name
Eosinophil peroxidase
Molecular Weight
81039.5 Da
References
  1. Lu T, Galijasevic S, Abdulhamid I, Abu-Soud HM: Analysis of the mechanism by which melatonin inhibits human eosinophil peroxidase. Br J Pharmacol. 2008 Jul;154(6):1308-17. doi: 10.1038/bjp.2008.173. Epub 2008 Jun 2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin/calnexin cycle. This lectin interacts transiently wit...
Gene Name
CALR
Uniprot ID
P27797
Uniprot Name
Calreticulin
Molecular Weight
48141.2 Da
References
  1. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [Article]
  2. Macias M, Escames G, Leon J, Coto A, Sbihi Y, Osuna A, Acuna-Castroviejo D: Calreticulin-melatonin. An unexpected relationship. Eur J Biochem. 2003 Mar;270(5):832-40. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name
ASMT
Uniprot ID
P46597
Uniprot Name
Acetylserotonin O-methyltransferase
Molecular Weight
38452.51 Da
References
  1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadph dehydrogenase (quinone) activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name
NQO2
Uniprot ID
P16083
Uniprot Name
Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight
25918.4 Da
References
  1. Radogna F, Paternoster L, De Nicola M, Cerella C, Ammendola S, Bedini A, Tarzia G, Aquilano K, Ciriolo M, Ghibelli L: Rapid and transient stimulation of intracellular reactive oxygen species by melatonin in normal and tumor leukocytes. Toxicol Appl Pharmacol. 2009 Aug 15;239(1):37-45. doi: 10.1016/j.taap.2009.05.012. Epub 2009 May 19. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [Article]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [Article]
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
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [Article]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [Article]
  3. Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [Article]
  4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. [Article]
  5. Hartter S, Wang X, Weigmann H, Friedberg T, Arand M, Oesch F, Hiemke C: Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J Clin Psychopharmacol. 2001 Apr;21(2):167-74. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
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
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Chang TK, Chen J, Yang G, Yeung EY: Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J Pineal Res. 2010 Jan;48(1):55-64. doi: 10.1111/j.1600-079X.2009.00724.x. Epub 2009 Nov 16. [Article]
  2. Ma X, Idle JR, Krausz KW, Gonzalez FJ: Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. Epub 2004 Dec 22. [Article]
  3. Yu Z, Tian X, Peng Y, Sun Z, Wang C, Tang N, Li B, Jian Y, Wang W, Huo X, Ma X: Mitochondrial cytochrome P450 (CYP) 1B1 is responsible for melatonin-induced apoptosis in neural cancer cells. J Pineal Res. 2018 Aug;65(1):e12478. doi: 10.1111/jpi.12478. Epub 2018 Mar 25. [Article]
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
  1. Huuhka K, Riutta A, Haataja R, Ylitalo P, Leinonen E: The effect of CYP2C19 substrate on the metabolism of melatonin in the elderly: A randomized, double-blind, placebo-controlled study. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):447-50. [Article]
  2. Facciola G, Hidestrand M, von Bahr C, Tybring G: Cytochrome P450 isoforms involved in melatonin metabolism in human liver microsomes. Eur J Clin Pharmacol. 2001 Mar;56(12):881-8. doi: 10.1007/s002280000245. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
References
  1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name
ASMT
Uniprot ID
P46597
Uniprot Name
Acetylserotonin O-methyltransferase
Molecular Weight
38452.51 Da
References
  1. Minneman KP, Wurtman RJ: The pharmacology of the pineal gland. Annu Rev Pharmacol Toxicol. 1976;16:33-51. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Tryptophan 2,3-dioxygenase activity
Specific Function
Catalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, cont...
Gene Name
IDO1
Uniprot ID
P14902
Uniprot Name
Indoleamine 2,3-dioxygenase 1
Molecular Weight
45325.89 Da
References
  1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Ferry G, Ubeaud C, Lambert PH, Bertin S, Coge F, Chomarat P, Delagrange P, Serkiz B, Bouchet JP, Truscott RJ, Boutin JA: Molecular evidence that melatonin is enzymatically oxidized in a different manner than tryptophan: investigations with both indoleamine 2,3-dioxygenase and myeloperoxidase. Biochem J. 2005 May 15;388(Pt 1):205-15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Gonzalez A, Martinez-Campa C, Mediavilla MD, Alonso-Gonzalez C, Sanchez-Mateos S, Hill SM, Sanchez-Barcelo EJ, Cos S: Effects of MT1 melatonin receptor overexpression on the aromatase-suppressive effect of melatonin in MCF-7 human breast cancer cells. Oncol Rep. 2007 Apr;17(4):947-53. doi: 10.3892/or.17.4.947. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [Article]
  2. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 22, 2022 01:06