Identification

Name
Melatonin
Accession Number
DB01065  (APRD00742, DB08189)
Type
Small Molecule
Groups
Approved, Nutraceutical, Vet Approved
Description

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.

Structure
Thumb
Synonyms
  • 5-methoxy-N-acetyltryptamine
  • Melatonin
  • Melatonine
  • N-[2-(5-methoxyindol-3-yl)ethyl]acetamide
  • N-Acetyl-5-methoxytryptamine
External IDs
BCI-049 / J5.258B / NSC-113928 / NSC-56423
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Limited2007-06-29Not applicableEu
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Limited2007-06-29Not applicableEu
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Limited2007-06-29Not applicableEu
CircadinTablet, extended release2 mgOralRad Neurim Pharmaceuticals Eec Limited2007-06-29Not applicableEu
International/Other Brands
Circadin (Lundbeck (France, United Kingdom), Neurim Pharmaceutical Labs (Israel, Denmark, Greece, Norway, Poland, Portugal), Nycomed (Belgium, Sweden)) / 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))
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Medi-doze Rx Sleep AidMelatonin (6 mg/1) + Valerian (50 mg/1) + gamma-Aminobutyric acid (30 mg/1)TabletOralTwo Hip Consulting, Llc2013-02-202016-04-05Us
Categories
UNII
JL5DK93RCL
CAS number
73-31-4
Weight
Average: 232.2783
Monoisotopic: 232.121177766
Chemical Formula
C13H16N2O2
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

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.

Structured Indications
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
Human
AMelatonin receptor type 1B
agonist
Human
UEstrogen receptor alpha
antagonist
Human
UNuclear receptor ROR-beta
agonist
Human
UCalmodulinNot AvailableHuman
UMyeloperoxidase
inhibitor
Human
UEosinophil peroxidase
inhibitor
Human
UCalreticulinNot AvailableHuman
UAcetylserotonin O-methyltransferaseNot AvailableHuman
URibosyldihydronicotinamide dehydrogenase [quinone]Not AvailableHuman
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).

Route of elimination
Not Available
Half life

35 to 50 minutes

Clearance
Not Available
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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7-NitroindazoleThe risk or severity of adverse effects can be increased when Melatonin is combined with 7-Nitroindazole.Experimental
AbirateroneThe serum concentration of Melatonin can be increased when it is combined with Abiraterone.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Aceprometazine.Approved
AdipiplonThe risk or severity of adverse effects can be increased when Melatonin is combined with Adipiplon.Investigational
AgomelatineThe risk or severity of adverse effects can be increased when Melatonin is combined with Agomelatine.Approved, Investigational
AlaproclateThe risk or severity of adverse effects can be increased when Melatonin is combined with Alaproclate.Experimental
AlfaxaloneThe risk or severity of adverse effects can be increased when Melatonin is combined with Alfaxalone.Vet Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Melatonin.Approved, Illicit
AllopregnanoloneThe risk or severity of adverse effects can be increased when Melatonin is combined with Allopregnanolone.Investigational
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Melatonin is combined with Alphacetylmethadol.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Melatonin is combined with Alphaprodine.Illicit
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Melatonin.Approved, Illicit, Investigational
AmiodaroneThe metabolism of Melatonin can be decreased when combined with Amiodarone.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Melatonin is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Melatonin is combined with Amitriptyline.Approved
AmlodipineMelatonin may decrease the antihypertensive activities of Amlodipine.Approved
AmobarbitalThe risk or severity of adverse effects can be increased when Amobarbital is combined with Melatonin.Approved, Illicit
AmoxapineThe risk or severity of adverse effects can be increased when Melatonin is combined with Amoxapine.Approved
AmperozideThe risk or severity of adverse effects can be increased when Melatonin is combined with Amperozide.Experimental
AprepitantThe metabolism of Melatonin can be increased when combined with Aprepitant.Approved, Investigational
AripiprazoleThe risk or severity of adverse effects can be increased when Aripiprazole is combined with Melatonin.Approved, Investigational
ArmodafinilThe metabolism of Melatonin can be decreased when combined with Armodafinil.Approved, Investigational
ArticaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Articaine.Approved
AsenapineThe risk or severity of adverse effects can be increased when Asenapine is combined with Melatonin.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Azaperone.Vet Approved
AzelastineMelatonin may increase the central nervous system depressant (CNS depressant) activities of Azelastine.Approved
AzithromycinThe metabolism of Melatonin can be decreased when combined with Azithromycin.Approved
BaclofenThe risk or severity of adverse effects can be increased when Melatonin is combined with Baclofen.Approved
BarbitalThe risk or severity of adverse effects can be increased when Melatonin is combined with Barbital.Illicit
BenperidolThe risk or severity of adverse effects can be increased when Melatonin is combined with Benperidol.Investigational
BenzocaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Benzocaine.Approved
Benzyl alcoholThe risk or severity of adverse effects can be increased when Melatonin is combined with Benzyl alcohol.Approved
BortezomibThe metabolism of Melatonin can be decreased when combined with Bortezomib.Approved, Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Melatonin is combined with Brexpiprazole.Approved
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved
BromazepamThe risk or severity of adverse effects can be increased when Bromazepam is combined with Melatonin.Approved, Illicit
BromisovalThe risk or severity of adverse effects can be increased when Melatonin is combined with Bromisoval.Experimental
BromperidolThe risk or severity of adverse effects can be increased when Melatonin is combined with Bromperidol.Investigational
BrompheniramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Brompheniramine.Approved
BrotizolamThe risk or severity of adverse effects can be increased when Melatonin is combined with Brotizolam.Approved, Withdrawn
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Melatonin.Approved, Investigational
BuprenorphineMelatonin may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Melatonin.Approved, Investigational
ButabarbitalThe risk or severity of adverse effects can be increased when Butabarbital is combined with Melatonin.Approved, Illicit
ButacaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Butacaine.Vet Approved
ButalbitalThe risk or severity of adverse effects can be increased when Melatonin is combined with Butalbital.Approved, Illicit
ButambenThe risk or severity of adverse effects can be increased when Melatonin is combined with Butamben.Approved
ButethalThe risk or severity of adverse effects can be increased when Melatonin is combined with Butethal.Approved, Illicit
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Melatonin.Approved, Illicit, Vet Approved
CaffeineThe metabolism of Melatonin can be decreased when combined with Caffeine.Approved
CanertinibThe risk or severity of adverse effects can be increased when Melatonin is combined with Canertinib.Investigational
CapecitabineThe metabolism of Melatonin can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Melatonin can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Carbinoxamine.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Melatonin is combined with Carfentanil.Illicit, Vet Approved
CarisoprodolThe risk or severity of adverse effects can be increased when Melatonin is combined with Carisoprodol.Approved
CeritinibThe serum concentration of Melatonin can be increased when it is combined with Ceritinib.Approved
CetirizineThe risk or severity of adverse effects can be increased when Melatonin is combined with Cetirizine.Approved
Chloral hydrateThe risk or severity of adverse effects can be increased when Melatonin is combined with Chloral hydrate.Approved, Illicit, Vet Approved
ChloramphenicolThe metabolism of Melatonin can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlordiazepoxideThe risk or severity of adverse effects can be increased when Chlordiazepoxide is combined with Melatonin.Approved, Illicit
ChlormezanoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Chlormezanone.Approved, Withdrawn
ChloroprocaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Chloroprocaine.Approved
ChlorphenamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Chlorphenamine.Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Melatonin.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Melatonin is combined with Chlorprothixene.Approved, Withdrawn
ChlorzoxazoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Chlorzoxazone.Approved
CholecalciferolThe metabolism of Melatonin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Melatonin can be decreased when combined with Cimetidine.Approved
CinchocaineThe risk or severity of adverse effects can be increased when Cinchocaine is combined with Melatonin.Approved, Vet Approved
CitalopramThe metabolism of Melatonin can be decreased when combined with Citalopram.Approved
ClemastineThe risk or severity of adverse effects can be increased when Melatonin is combined with Clemastine.Approved
ClevidipineMelatonin may decrease the antihypertensive activities of Clevidipine.Approved
ClidiniumThe risk or severity of adverse effects can be increased when Melatonin is combined with Clidinium.Approved
ClobazamThe risk or severity of adverse effects can be increased when Melatonin is combined with Clobazam.Approved, Illicit
clomethiazoleThe risk or severity of adverse effects can be increased when Melatonin is combined with clomethiazole.Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Clomipramine.Approved, Vet Approved
ClonazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Clonazepam.Approved, Illicit
ClonidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Clonidine.Approved
ClopenthixolThe risk or severity of adverse effects can be increased when Melatonin is combined with Clopenthixol.Experimental
ClorazepateThe risk or severity of adverse effects can be increased when Clorazepate is combined with Melatonin.Approved, Illicit
ClothiapineThe risk or severity of adverse effects can be increased when Melatonin is combined with Clothiapine.Experimental
ClotrimazoleThe metabolism of Melatonin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Melatonin.Approved
CocaineThe risk or severity of adverse effects can be increased when Cocaine is combined with Melatonin.Approved, Illicit
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Melatonin.Approved, Illicit
CrisaboroleThe metabolism of Melatonin can be decreased when combined with Crisaborole.Approved
CyclizineThe risk or severity of adverse effects can be increased when Melatonin is combined with Cyclizine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Melatonin.Approved
CyclosporineThe metabolism of Melatonin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyproheptadineThe risk or severity of adverse effects can be increased when Melatonin is combined with Cyproheptadine.Approved
Cyproterone acetateThe serum concentration of Melatonin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Melatonin can be decreased when it is combined with Dabrafenib.Approved
DantroleneThe risk or severity of adverse effects can be increased when Melatonin is combined with Dantrolene.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Dapiprazole is combined with Melatonin.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dapoxetine.Investigational
DeferasiroxThe serum concentration of Melatonin can be increased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Melatonin can be decreased when combined with Delavirdine.Approved
DeramciclaneThe risk or severity of adverse effects can be increased when Melatonin is combined with Deramciclane.Investigational
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Melatonin.Approved
DesipramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Desipramine.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Melatonin is combined with Desloratadine.Approved, Investigational
DesvenlafaxineThe risk or severity of adverse effects can be increased when Melatonin is combined with Desvenlafaxine.Approved
DetomidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Detomidine.Vet Approved
DexbrompheniramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dexbrompheniramine.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Melatonin.Approved, Vet Approved
DextromoramideThe risk or severity of adverse effects can be increased when Melatonin is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Melatonin.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dezocine.Approved
DiazepamThe risk or severity of adverse effects can be increased when Diazepam is combined with Melatonin.Approved, Illicit, Vet Approved
Diethyl etherThe risk or severity of adverse effects can be increased when Melatonin is combined with Diethyl ether.Experimental
DifenoxinThe risk or severity of adverse effects can be increased when Melatonin is combined with Difenoxin.Approved, Illicit
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Melatonin.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dihydromorphine.Experimental, Illicit
DimenhydrinateThe risk or severity of adverse effects can be increased when Melatonin is combined with Dimenhydrinate.Approved
DiphenhydramineThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with Melatonin.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Melatonin.Approved, Illicit
DixyrazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Dixyrazine.Experimental
DoramectinThe risk or severity of adverse effects can be increased when Melatonin is combined with Doramectin.Vet Approved
DosulepinThe metabolism of Melatonin can be decreased when combined with Dosulepin.Approved
DoxepinThe risk or severity of adverse effects can be increased when Melatonin is combined with Doxepin.Approved
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Vet Approved
DPDPEThe risk or severity of adverse effects can be increased when Melatonin is combined with DPDPE.Investigational
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Illicit
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Vet Approved
DrotebanolThe risk or severity of adverse effects can be increased when Melatonin is combined with Drotebanol.Experimental, Illicit
DuloxetineThe risk or severity of adverse effects can be increased when Melatonin is combined with Duloxetine.Approved
DyclonineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Melatonin.Approved
EcgonineThe risk or severity of adverse effects can be increased when Melatonin is combined with Ecgonine.Experimental, Illicit
EcopipamThe risk or severity of adverse effects can be increased when Melatonin is combined with Ecopipam.Investigational
EfavirenzThe risk or severity of adverse effects can be increased when Melatonin is combined with Efavirenz.Approved, Investigational
EltanoloneThe risk or severity of adverse effects can be increased when Melatonin is combined with Eltanolone.Investigational
EnfluraneThe risk or severity of adverse effects can be increased when Enflurane is combined with Melatonin.Approved, Vet Approved
EntacaponeThe risk or severity of adverse effects can be increased when Melatonin is combined with Entacapone.Approved, Investigational
EscitalopramThe risk or severity of adverse effects can be increased when Melatonin is combined with Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Melatonin can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Melatonin can be decreased when combined with Esomeprazole.Approved, Investigational
EstazolamThe risk or severity of adverse effects can be increased when Estazolam is combined with Melatonin.Approved, Illicit
EszopicloneThe risk or severity of adverse effects can be increased when Eszopiclone is combined with Melatonin.Approved
EthanolMelatonin may increase the central nervous system depressant (CNS depressant) activities of Ethanol.Approved
EthchlorvynolThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Melatonin.Approved, Illicit, Withdrawn
EthosuximideThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethosuximide.Approved
EthotoinThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethotoin.Approved
Ethyl carbamateThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethyl carbamate.Withdrawn
Ethyl chlorideThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethyl chloride.Experimental
Ethyl loflazepateThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethyl loflazepate.Approved, Illicit
EthylmorphineThe risk or severity of adverse effects can be increased when Melatonin is combined with Ethylmorphine.Approved, Illicit
EtidocaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Etidocaine.Approved
EtifoxineThe risk or severity of adverse effects can be increased when Melatonin is combined with Etifoxine.Withdrawn
EtizolamThe risk or severity of adverse effects can be increased when Melatonin is combined with Etizolam.Approved
EtomidateThe risk or severity of adverse effects can be increased when Etomidate is combined with Melatonin.Approved
EtoperidoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Etoperidone.Approved
EtorphineThe risk or severity of adverse effects can be increased when Melatonin is combined with Etorphine.Illicit, Vet Approved
EtravirineThe metabolism of Melatonin can be decreased when combined with Etravirine.Approved
EzogabineThe risk or severity of adverse effects can be increased when Melatonin is combined with Ezogabine.Approved
FelbamateThe risk or severity of adverse effects can be increased when Melatonin is combined with Felbamate.Approved
FelodipineMelatonin may decrease the antihypertensive activities of Felodipine.Approved, Investigational
FencamfamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Melatonin.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe risk or severity of adverse effects can be increased when Melatonin is combined with Fexofenadine.Approved
FlibanserinThe risk or severity of adverse effects can be increased when Melatonin is combined with Flibanserin.Approved
FloxuridineThe metabolism of Melatonin can be decreased when combined with Floxuridine.Approved
FluanisoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Fluanisone.Experimental
FluconazoleThe metabolism of Melatonin can be decreased when combined with Fluconazole.Approved
FludiazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Fludiazepam.Approved, Illicit
FlunarizineThe risk or severity of adverse effects can be increased when Melatonin is combined with Flunarizine.Approved
FlunitrazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Flunitrazepam.Approved, Illicit
FluorouracilThe metabolism of Melatonin can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Melatonin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Flupentixol is combined with Melatonin.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Fluphenazine is combined with Melatonin.Approved
FlurazepamThe risk or severity of adverse effects can be increased when Flurazepam is combined with Melatonin.Approved, Illicit
FluspirileneThe risk or severity of adverse effects can be increased when Melatonin is combined with Fluspirilene.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Melatonin is combined with Fluticasone propionate.Approved
FluvastatinThe metabolism of Melatonin can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Melatonin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Melatonin can be increased when combined with Fosphenytoin.Approved
FospropofolThe risk or severity of adverse effects can be increased when Melatonin is combined with Fospropofol.Approved, Illicit
GabapentinThe risk or severity of adverse effects can be increased when Gabapentin is combined with Melatonin.Approved, Investigational
Gabapentin EnacarbilThe risk or severity of adverse effects can be increased when Melatonin is combined with Gabapentin Enacarbil.Approved
Gamma Hydroxybutyric AcidThe risk or severity of adverse effects can be increased when Gamma Hydroxybutyric Acid is combined with Melatonin.Approved, Illicit
GemfibrozilThe metabolism of Melatonin can be decreased when combined with Gemfibrozil.Approved
GepironeThe risk or severity of adverse effects can be increased when Melatonin is combined with Gepirone.Investigational
GlutethimideThe risk or severity of adverse effects can be increased when Melatonin is combined with Glutethimide.Approved, Illicit
GuanfacineThe risk or severity of adverse effects can be increased when Melatonin is combined with Guanfacine.Approved, Investigational
HalazepamThe risk or severity of adverse effects can be increased when Halazepam is combined with Melatonin.Approved, Illicit, Withdrawn
HaloperidolThe risk or severity of adverse effects can be increased when Haloperidol is combined with Melatonin.Approved
HalothaneThe risk or severity of adverse effects can be increased when Melatonin is combined with Halothane.Approved, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Melatonin is combined with Heroin.Approved, Illicit
HexobarbitalThe risk or severity of adverse effects can be increased when Melatonin is combined with Hexobarbital.Approved
HydrocodoneMelatonin may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Melatonin.Approved, Illicit
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Imipramine.Approved
IndalpineThe risk or severity of adverse effects can be increased when Melatonin is combined with Indalpine.Investigational, Withdrawn
IndinavirThe metabolism of Melatonin can be decreased when combined with Indinavir.Approved
IndiplonThe risk or severity of adverse effects can be increased when Melatonin is combined with Indiplon.Investigational
IrbesartanThe metabolism of Melatonin can be decreased when combined with Irbesartan.Approved, Investigational
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Melatonin.Approved, Vet Approved
IsoniazidThe metabolism of Melatonin can be decreased when combined with Isoniazid.Approved
IsradipineMelatonin may decrease the antihypertensive activities of Isradipine.Approved
KetamineThe risk or severity of adverse effects can be increased when Ketamine is combined with Melatonin.Approved, Vet Approved
KetazolamThe risk or severity of adverse effects can be increased when Melatonin is combined with Ketazolam.Approved
KetobemidoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Ketobemidone.Approved
KetoconazoleThe metabolism of Melatonin can be decreased when combined with Ketoconazole.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Melatonin is combined with Lamotrigine.Approved, Investigational
LeflunomideThe metabolism of Melatonin can be decreased when combined with Leflunomide.Approved, Investigational
LevetiracetamThe risk or severity of adverse effects can be increased when Melatonin is combined with Levetiracetam.Approved, Investigational
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Melatonin.Approved
LevocabastineThe risk or severity of adverse effects can be increased when Melatonin is combined with Levocabastine.Approved
LevocetirizineThe risk or severity of adverse effects can be increased when Melatonin is combined with Levocetirizine.Approved
LevodopaThe risk or severity of adverse effects can be increased when Melatonin is combined with Levodopa.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Melatonin is combined with Levomethadyl Acetate.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Melatonin is combined with Levomilnacipran.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Melatonin.Approved
LidocaineThe metabolism of Melatonin can be decreased when combined with Lidocaine.Approved, Vet Approved
LithiumThe risk or severity of adverse effects can be increased when Melatonin is combined with Lithium.Approved
LobeglitazoneThe metabolism of Melatonin can be decreased when combined with Lobeglitazone.Approved
LofentanilThe risk or severity of adverse effects can be increased when Melatonin is combined with Lofentanil.Illicit
LopinavirThe metabolism of Melatonin can be increased when combined with Lopinavir.Approved
LoprazolamThe risk or severity of adverse effects can be increased when Melatonin is combined with Loprazolam.Experimental
LoratadineThe risk or severity of adverse effects can be increased when Melatonin is combined with Loratadine.Approved
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Melatonin.Approved
LormetazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Lormetazepam.Approved
LosartanThe metabolism of Melatonin can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Melatonin can be decreased when combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Loxapine is combined with Melatonin.Approved
LuliconazoleThe serum concentration of Melatonin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Melatonin can be decreased when it is combined with Lumacaftor.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Lurasidone is combined with Melatonin.Approved
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Vet Approved
ManidipineThe metabolism of Melatonin can be decreased when combined with Manidipine.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Melatonin is combined with Maprotiline.Approved
MebicarThe risk or severity of adverse effects can be increased when Melatonin is combined with Mebicar.Experimental
MeclizineThe risk or severity of adverse effects can be increased when Melatonin is combined with Meclizine.Approved
MedazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Medazepam.Experimental
MedetomidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Medetomidine.Vet Approved
MelperoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Melperone.Approved
MepivacaineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with Melatonin.Approved, Vet Approved
MeprobamateThe risk or severity of adverse effects can be increased when Meprobamate is combined with Melatonin.Approved, Illicit
MeptazinolThe risk or severity of adverse effects can be increased when Melatonin is combined with Meptazinol.Experimental
MesoridazineThe risk or severity of adverse effects can be increased when Mesoridazine is combined with Melatonin.Approved
MetaxaloneThe risk or severity of adverse effects can be increased when Melatonin is combined with Metaxalone.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Melatonin.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Melatonin is combined with Methadyl Acetate.Approved, Illicit
MethapyrileneThe risk or severity of adverse effects can be increased when Melatonin is combined with Methapyrilene.Withdrawn
MethaqualoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Methaqualone.Illicit, Withdrawn
MethocarbamolThe risk or severity of adverse effects can be increased when Melatonin is combined with Methocarbamol.Approved, Vet Approved
MethohexitalThe risk or severity of adverse effects can be increased when Methohexital is combined with Melatonin.Approved
MethotrimeprazineMelatonin may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.Approved
MethoxyfluraneThe risk or severity of adverse effects can be increased when Methoxyflurane is combined with Melatonin.Approved, Vet Approved
MethsuximideThe risk or severity of adverse effects can be increased when Melatonin is combined with Methsuximide.Approved
MethylecgonineThe risk or severity of adverse effects can be increased when Melatonin is combined with Methylecgonine.Experimental
MethylphenobarbitalThe risk or severity of adverse effects can be increased when Methylphenobarbital is combined with Melatonin.Approved
MetyrosineMelatonin may increase the sedative activities of Metyrosine.Approved
MexiletineThe metabolism of Melatonin can be decreased when combined with Mexiletine.Approved
MidazolamThe risk or severity of adverse effects can be increased when Midazolam is combined with Melatonin.Approved, Illicit
MidostaurinThe metabolism of Melatonin can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Melatonin can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Melatonin is combined with Milnacipran.Approved
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Investigational
MirtazapineMelatonin may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.Approved
MoclobemideThe metabolism of Melatonin can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Melatonin can be decreased when combined with Modafinil.Approved, Investigational
MolindoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Molindone.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Melatonin.Approved, Investigational
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Melatonin.Approved
NefazodoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Melatonin can be decreased when combined with Nelfinavir.Approved
NevirapineThe metabolism of Melatonin can be decreased when combined with Nevirapine.Approved
NicardipineMelatonin may decrease the antihypertensive activities of Nicardipine.Approved
NifedipineMelatonin may decrease the antihypertensive activities of Nifedipine.Approved
NimodipineMelatonin may decrease the antihypertensive activities of Nimodipine.Approved
NisoldipineMelatonin may decrease the antihypertensive activities of Nisoldipine.Approved
NitrazepamThe risk or severity of adverse effects can be increased when Nitrazepam is combined with Melatonin.Approved
Nitrous oxideThe risk or severity of adverse effects can be increased when Nitrous oxide is combined with Melatonin.Approved, Vet Approved
NorfluraneThe risk or severity of adverse effects can be increased when Melatonin is combined with Norflurane.Investigational
NormethadoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Normethadone.Approved, Illicit
NortriptylineThe risk or severity of adverse effects can be increased when Melatonin is combined with Nortriptyline.Approved
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Melatonin.Approved, Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Melatonin is combined with Olopatadine.Approved
OmeprazoleThe metabolism of Melatonin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronThe risk or severity of adverse effects can be increased when Ondansetron is combined with Melatonin.Approved
OpiumThe risk or severity of adverse effects can be increased when Melatonin is combined with Opium.Approved, Illicit
OrphenadrineMelatonin may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.Approved
OsanetantThe risk or severity of adverse effects can be increased when Melatonin is combined with Osanetant.Investigational
OsimertinibThe serum concentration of Melatonin can be decreased when it is combined with Osimertinib.Approved
OxazepamThe risk or severity of adverse effects can be increased when Oxazepam is combined with Melatonin.Approved
OxethazaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Oxethazaine.Investigational
OxprenololThe risk or severity of adverse effects can be increased when Melatonin is combined with Oxprenolol.Approved
OxybuprocaineThe risk or severity of adverse effects can be increased when Oxybuprocaine is combined with Melatonin.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Melatonin.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Melatonin.Approved, Investigational, Vet Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Paliperidone is combined with Melatonin.Approved
PantoprazoleThe metabolism of Melatonin can be decreased when combined with Pantoprazole.Approved
ParaldehydeMelatonin may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Melatonin is combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Melatonin can be increased when it is combined with Peginterferon alfa-2b.Approved
PenfluridolThe risk or severity of adverse effects can be increased when Melatonin is combined with Penfluridol.Experimental
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Melatonin.Approved, Vet Approved
PentobarbitalThe risk or severity of adverse effects can be increased when Pentobarbital is combined with Melatonin.Approved, Vet Approved
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved
PerazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Melatonin is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Melatonin.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Melatonin.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Melatonin is combined with Phenazocine.Experimental
PhenibutThe risk or severity of adverse effects can be increased when Melatonin is combined with Phenibut.Experimental
PhenobarbitalThe metabolism of Melatonin can be increased when combined with Phenobarbital.Approved
PhenoperidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Phenoperidine.Experimental
PhenoxyethanolThe risk or severity of adverse effects can be increased when Melatonin is combined with Phenoxyethanol.Approved
PhenytoinThe metabolism of Melatonin can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideThe risk or severity of adverse effects can be increased when Pimozide is combined with Melatonin.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Melatonin is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Pipotiazine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Melatonin is combined with Piritramide.Investigational
PizotifenThe risk or severity of adverse effects can be increased when Melatonin is combined with Pizotifen.Approved
PomalidomideThe risk or severity of adverse effects can be increased when Melatonin is combined with Pomalidomide.Approved
PramipexoleMelatonin may increase the sedative activities of Pramipexole.Approved, Investigational
PramocaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Pramocaine.Approved
PrazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Prazepam.Approved, Illicit
PregabalinThe risk or severity of adverse effects can be increased when Pregabalin is combined with Melatonin.Approved, Illicit, Investigational
PrilocaineThe risk or severity of adverse effects can be increased when Prilocaine is combined with Melatonin.Approved
PrimidoneThe metabolism of Melatonin can be increased when combined with Primidone.Approved, Vet Approved
ProcaineThe risk or severity of adverse effects can be increased when Procaine is combined with Melatonin.Approved, Investigational, Vet Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Melatonin.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Promazine is combined with Melatonin.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Promethazine.Approved
PropanididThe risk or severity of adverse effects can be increased when Melatonin is combined with Propanidid.Experimental
ProparacaineThe risk or severity of adverse effects can be increased when Proparacaine is combined with Melatonin.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Propofol is combined with Melatonin.Approved, Investigational, Vet Approved
PropoxycaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Propoxycaine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Melatonin is combined with Protriptyline.Approved
ProxibarbalThe risk or severity of adverse effects can be increased when Melatonin is combined with Proxibarbal.Experimental
PSD502The risk or severity of adverse effects can be increased when Melatonin is combined with PSD502.Investigational
PyrimethamineThe metabolism of Melatonin can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe risk or severity of adverse effects can be increased when Quazepam is combined with Melatonin.Approved, Illicit
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Melatonin.Approved
QuinineThe metabolism of Melatonin can be decreased when combined with Quinine.Approved
QuinisocaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Quinisocaine.Experimental
RacloprideThe risk or severity of adverse effects can be increased when Melatonin is combined with Raclopride.Investigational
RamelteonThe risk or severity of adverse effects can be increased when Melatonin is combined with Ramelteon.Approved, Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Melatonin.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Remoxipride is combined with Melatonin.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Melatonin.Approved
RifampicinThe metabolism of Melatonin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Melatonin can be increased when combined with Rifapentine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Risperidone is combined with Melatonin.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Melatonin is combined with Ritanserin.Investigational
RomifidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Romifidine.Vet Approved
RopiniroleMelatonin may increase the sedative activities of Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Ropivacaine is combined with Melatonin.Approved
RotigotineMelatonin may increase the sedative activities of Rotigotine.Approved
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Melatonin.Approved
ScopolamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Scopolamine.Approved
SecobarbitalThe metabolism of Melatonin can be increased when combined with Secobarbital.Approved, Vet Approved
SepranoloneThe risk or severity of adverse effects can be increased when Melatonin is combined with Sepranolone.Investigational
SertindoleThe risk or severity of adverse effects can be increased when Melatonin is combined with Sertindole.Approved, Withdrawn
SertralineThe metabolism of Melatonin can be decreased when combined with Sertraline.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Sevoflurane is combined with Melatonin.Approved, Vet Approved
SildenafilThe metabolism of Melatonin can be decreased when combined with Sildenafil.Approved, Investigational
SimeprevirThe metabolism of Melatonin can be decreased when combined with Simeprevir.Approved
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved
SorafenibThe metabolism of Melatonin can be decreased when combined with Sorafenib.Approved, Investigational
StiripentolThe metabolism of Melatonin can be decreased when combined with Stiripentol.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Melatonin.Approved, Investigational
SulfadiazineThe metabolism of Melatonin can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Melatonin can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Melatonin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Sulpiride is combined with Melatonin.Approved
SultoprideThe risk or severity of adverse effects can be increased when Melatonin is combined with Sultopride.Experimental
SuvorexantMelatonin may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.Approved
TandospironeThe risk or severity of adverse effects can be increased when Melatonin is combined with Tandospirone.Investigational
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Melatonin.Approved
TasimelteonThe risk or severity of adverse effects can be increased when Melatonin is combined with Tasimelteon.Approved
TemazepamThe risk or severity of adverse effects can be increased when Temazepam is combined with Melatonin.Approved
Tenofovir disoproxilThe metabolism of Melatonin can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Melatonin can be decreased when it is combined with Teriflunomide.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tetrabenazine.Approved
TetracaineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tetracaine.Approved, Vet Approved
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tetrahydropalmatine.Investigational
TetrodotoxinThe risk or severity of adverse effects can be increased when Melatonin is combined with Tetrodotoxin.Investigational
ThalidomideMelatonin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe metabolism of Melatonin can be decreased when combined with Theophylline.Approved
ThiamylalThe risk or severity of adverse effects can be increased when Melatonin is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe risk or severity of adverse effects can be increased when Thiopental is combined with Melatonin.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Thioridazine is combined with Melatonin.Withdrawn
ThiothixeneThe risk or severity of adverse effects can be increased when Thiothixene is combined with Melatonin.Approved
TiagabineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tiagabine.Approved
TiaprideThe risk or severity of adverse effects can be increased when Melatonin is combined with Tiapride.Approved, Investigational
TicagrelorThe metabolism of Melatonin can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Melatonin can be decreased when combined with Ticlopidine.Approved
TiletamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tiletamine.Vet Approved
TilidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tilidine.Experimental
TizanidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Tizanidine.Approved
TolbutamideThe metabolism of Melatonin can be decreased when combined with Tolbutamide.Approved
TolcaponeThe risk or severity of adverse effects can be increased when Melatonin is combined with Tolcapone.Approved, Withdrawn
TopiramateThe risk or severity of adverse effects can be increased when Melatonin is combined with Topiramate.Approved
TopiroxostatThe metabolism of Melatonin can be decreased when combined with Topiroxostat.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Melatonin.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Melatonin is combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Melatonin.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Melatonin.Approved, Investigational
TriazolamThe risk or severity of adverse effects can be increased when Triazolam is combined with Melatonin.Approved
Tricaine methanesulfonateThe risk or severity of adverse effects can be increased when Melatonin is combined with Tricaine methanesulfonate.Vet Approved
TrichloroethyleneThe risk or severity of adverse effects can be increased when Melatonin is combined with Trichloroethylene.Experimental
TrifluoperazineThe risk or severity of adverse effects can be increased when Trifluoperazine is combined with Melatonin.Approved
TrifluperidolThe risk or severity of adverse effects can be increased when Melatonin is combined with Trifluperidol.Experimental
TriflupromazineThe risk or severity of adverse effects can be increased when Triflupromazine is combined with Melatonin.Approved, Vet Approved
TrimethoprimThe metabolism of Melatonin can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Melatonin is combined with Trimipramine.Approved
TriprolidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Triprolidine.Approved
Valproic AcidThe risk or severity of adverse effects can be increased when Valproic Acid is combined with Melatonin.Approved, Investigational
ValsartanThe metabolism of Melatonin can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Melatonin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Melatonin is combined with Venlafaxine.Approved
VeraliprideThe risk or severity of adverse effects can be increased when Melatonin is combined with Veralipride.Experimental
VigabatrinThe risk or severity of adverse effects can be increased when Melatonin is combined with Vigabatrin.Approved
Vinyl etherThe risk or severity of adverse effects can be increased when Melatonin is combined with Vinyl ether.Experimental
VoriconazoleThe metabolism of Melatonin can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe risk or severity of adverse effects can be increased when Melatonin is combined with Vortioxetine.Approved
XenonThe risk or severity of adverse effects can be increased when Melatonin is combined with Xenon.Experimental
XylazineThe risk or severity of adverse effects can be increased when Melatonin is combined with Xylazine.Vet Approved
ZafirlukastThe metabolism of Melatonin can be decreased when combined with Zafirlukast.Approved, Investigational
ZaleplonThe risk or severity of adverse effects can be increased when Zaleplon is combined with Melatonin.Approved, Illicit, Investigational
ZiconotideThe risk or severity of adverse effects can be increased when Melatonin is combined with Ziconotide.Approved
ZimelidineThe risk or severity of adverse effects can be increased when Melatonin is combined with Zimelidine.Withdrawn
ZiprasidoneThe risk or severity of adverse effects can be increased when Ziprasidone is combined with Melatonin.Approved
ZolazepamThe risk or severity of adverse effects can be increased when Melatonin is combined with Zolazepam.Vet Approved
ZolpidemMelatonin may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.Approved
ZonisamideThe risk or severity of adverse effects can be increased when Melatonin is combined with Zonisamide.Approved, Investigational
ZopicloneThe risk or severity of adverse effects can be increased when Zopiclone is combined with Melatonin.Approved
ZotepineThe risk or severity of adverse effects can be increased when Melatonin is combined with Zotepine.Approved
ZucapsaicinThe metabolism of Melatonin can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Zuclopenthixol is combined with Melatonin.Approved, Investigational
Food Interactions
Not Available

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. [PubMed:15992934 ]
  2. Caniato R, Filippini R, Piovan A, Puricelli L, Borsarini A, Cappelletti EM: Melatonin in plants. Adv Exp Med Biol. 2003;527:593-7. [PubMed:15206778 ]
  3. Hardeland R: Antioxidative protection by melatonin: multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine. 2005 Jul;27(2):119-30. [PubMed:16217125 ]
  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. [PubMed:7773197 ]
  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. [PubMed:18187545 ]
  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. [PubMed:11462772 ]
External Links
Human Metabolome Database
HMDB01389
KEGG Compound
C01598
PubChem Compound
896
PubChem Substance
46509101
ChemSpider
872
BindingDB
9019
ChEBI
16796
ChEMBL
CHEMBL45
Therapeutic Targets Database
DAP000429
PharmGKB
PA164752558
IUPHAR
1357
Guide to Pharmacology
GtP Drug Page
HET
ML1
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Melatonin
ATC Codes
N05CH01 — Melatonin
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (72 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentCancer, Breast1
0Enrolling by InvitationTreatmentDiabetes Mellitus (DM)1
0Not Yet RecruitingTreatmentAutonomic Nervous System Diseases / Hypertensive / Idiopathic orthostatic hypotension1
0Not Yet RecruitingTreatmentDiabetes, Diabetes Mellitus Type 1 / Hypertensive1
0RecruitingTreatmentHypoxic Ischemic Encephalopathy (HIE)1
1CompletedBasic ScienceHealthy Adult Subjects / Healthy Elderly Subjects1
1CompletedBasic ScienceSepsis1
1CompletedBasic ScienceSleep disorders and disturbances1
1CompletedBasic ScienceSpinal Cord Injured, Tetraplegia1
1CompletedPreventionReperfusion Injury1
1CompletedPreventionSolar Skin Damage1
1CompletedPreventionProphylaxis of Sunburn1
1RecruitingSupportive CareRelapsed Malignant Solid Tumor1
1TerminatedTreatmentCancer, Breast1
1Unknown StatusNot AvailableRheumatoid Arthritis1
1Unknown StatusEducational/Counseling/TrainingDelayed Sleep Phase Syndrome1
1WithdrawnTreatmentNewborn Hypoxic Ischemic Encephalopathy1
1, 2Active Not RecruitingPreventionOral Mucositis1
1, 2CompletedPreventionFeeling Anxious / Pain1
1, 2CompletedPreventionPost Partum Haemorrhage in Patients Undergoing Cesarean Section1
1, 2CompletedSupportive CareNeonatal Sepsis1
1, 2CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
1, 2CompletedTreatmentPerinatal Asphyxia1
1, 2Enrolling by InvitationOtherGlucose Metabolism Disorders1
1, 2Not Yet RecruitingSupportive CareQuality of Life1
1, 2RecruitingNot AvailablePharmacokinetics of Melatonin1
1, 2TerminatedTreatmentMenopausal Hot Flushes1
1, 2Unknown StatusTreatmentGastroesophageal Reflux Disease1
1, 2WithdrawnTreatmentSepsis1
2Active Not RecruitingTreatmentAdvanced Cancers1
2CompletedNot AvailableBrain Injury / Premature Births1
2CompletedPreventionHead and Neck Carcinoma1
2CompletedPreventionMigraines1
2CompletedPreventionSchizophrenic Disorders1
2CompletedTreatmentAcute Myocardial Infarction (AMI) / Ischemia-Reperfusion Injury1
2CompletedTreatmentAlzheimer's Disease (AD) / Sleep Disorder1
2CompletedTreatmentAutism, Early Infantile1
2CompletedTreatmentBlindness / Non-24 Hour Sleep-Wake Disorder1
2CompletedTreatmentDepressive State / Genotoxicity / Pain / Sleep Disorders, Circadian Rhythm1
2CompletedTreatmentEarly Stage Breast Cancer1
2CompletedTreatmentEpilepsies1
2CompletedTreatmentHypertensive2
2CompletedTreatmentHypertensive / Sleep disorders and disturbances1
2CompletedTreatmentJet Lag Syndrome1
2CompletedTreatmentMetabolic Syndromes1
2CompletedTreatmentMigraine in Adolescents1
2CompletedTreatmentPrimary Insomnia1
2CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
2CompletedTreatmentSleep Initiation and Maintenance Disorders1
2CompletedTreatmentSleeplessness / Type 2 Diabetes Mellitus1
2CompletedTreatmentTiredness1
2Not Yet RecruitingPreventionDelirium1
2Not Yet RecruitingPreventionMigraines1
2Not Yet RecruitingTreatmentParkinson's Disease (PD) / REM Sleep Behavior Disorder1
2RecruitingPreventionNonvalvular Atrial Fibrillation1
2RecruitingTreatmentAutism Spectrum Conditions/Disorders1
2RecruitingTreatmentCancer, Breast3
2RecruitingTreatmentDentofacial Deformity1
2RecruitingTreatmentMelanoma1
2RecruitingTreatmentReperfusion Injury1
2RecruitingTreatmentSleep disorders and disturbances1
2TerminatedTreatmentAcute Myocardial Infarction (AMI)1
2TerminatedTreatmentMinor burns / Pediatric Burns1
2Unknown StatusNot AvailableInflammatory Stress / Myocardial Ischemia / Oxidative Stress1
2Unknown StatusBasic ScienceAnalgesia Disorder / Pain1
2Unknown StatusTreatmentMild Cognitive Impairment (MCI)1
2Unknown StatusTreatmentNocturia / Parkinson's Disease (PD)1
2Unknown StatusTreatmentNocturnal Enuresis1
2WithdrawnTreatmentHeart Failure, Unspecified / Sleep disorders and disturbances1
2, 3Active Not RecruitingTreatmentAcute Coronary Syndromes (ACS) / Depressive State1
2, 3CompletedBasic ScienceAnalgesia / Antihyperalgesia1
2, 3CompletedPreventionAortic Aneurysms1
2, 3CompletedTreatmentAdvanced Stage Cancer1
2, 3CompletedTreatmentCancers / Tiredness1
2, 3CompletedTreatmentDyssomnias / Postoperative Complications / Tiredness1
2, 3Not Yet RecruitingTreatmentAutism Spectrum Conditions/Disorders / Sleep disorders and disturbances1
2, 3Not Yet RecruitingTreatmentInsomnia Disorder1
2, 3RecruitingTreatmentAssisted Reproductive Technology therapy / Poor Ovarian Response1
2, 3RecruitingTreatmentChronic Kidney Disease (CKD) / End Stage Renal Disease (ESRD) / Sleep Disorder1
2, 3RecruitingTreatmentPremature Births1
2, 3TerminatedTreatmentCancer, Breast / Depressive State1
2, 3Unknown StatusTreatmentFibromyalgia1
2, 3Unknown StatusTreatmentStage II and III Breast Cancer1
3Active Not RecruitingTreatmentSleep disorders and disturbances1
3CompletedBasic ScienceDiabetes / Glucose Tolerance1
3CompletedPreventionHealthy Night Shift Workers, Sleep Disorders / Sleep Disorders, Circadian Rhythm1
3CompletedTreatmentAlzheimer's Disease (AD) / Dyssomnias1
3CompletedTreatmentCancer Malignancies1
3CompletedTreatmentGastrointestinal Cancers / Lung Cancers1
3CompletedTreatmentHaemodialysis / Sleep disorders and disturbances1
3CompletedTreatmentMigraines1
3CompletedTreatmentHemodialysis-dependent patients / Peritoneal dialysis therapy / Sleep disorders and disturbances1
3CompletedTreatmentPrimary Insomnia1
3Not Yet RecruitingTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
3Not Yet RecruitingTreatmentFeeling Anxious / Pain1
3Not Yet RecruitingTreatmentNeurodevelopmental Disorders / Sleep disorders and disturbances1
3RecruitingBasic ScienceBMI >30 kg/m2 / Prediabetic State2
3RecruitingPreventionDelirium2
3RecruitingSupportive CareBreast Cancer - Female1
3RecruitingSupportive CareCancers1
3RecruitingTreatmentAnxiety Disorders / Dementias / Depressive State / Psychosomatic Disorders / Schizophrenic Disorders1
3Unknown StatusPreventionEsophagus, Barrett1
3Unknown StatusPreventionEvidence of Liver Transplantation1
3Unknown StatusTreatmentBenzodiazepines1
3Unknown StatusTreatmentSevere Sepsis / Shock, Septic1
3WithdrawnTreatmentGastroesophageal Reflux Disease1
4Active Not RecruitingTreatmentPostoperative pain1
4CompletedNot AvailablePostural Instability1
4CompletedPreventionHuman Endotoxaemia1
4CompletedPreventionSmoking / Vascular System Injuries1
4CompletedTreatmentAnaesthesia / Premedication1
4CompletedTreatmentBipolar Affective Disorders / Schizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentCritically Ill Patients / Mechanically Ventilated Patients1
4CompletedTreatmentDementias / Sleep disorders and disturbances1
4CompletedTreatmentFeeling Anxious1
4CompletedTreatmentHepatic Disease1
4CompletedTreatmentIntrauterine Growth Retardation1
4CompletedTreatmentRecovery From Bariatric Surgery1
4CompletedTreatmentSecond Generation Antipsychotic Induced Metabolic Adverse Effects1
4Enrolling by InvitationTreatmentParkinson's Disease (PD)2
4Not Yet RecruitingPreventionDelirium1
4RecruitingPreventionDelirium / Melatonin1
4RecruitingTreatmentCarotid Stenosis1
4RecruitingTreatmentREM Sleep Behavior Disorder1
4Unknown StatusTreatmentAcute Ischemic Stroke (AIS)1
4Unknown StatusTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Sleep Onset Insomnia1
4Unknown StatusTreatmentLennox-Gastaut Syndrome (LGS)1
4WithdrawnPreventionDelirium1
Not AvailableActive Not RecruitingTreatmentBipolar Disorder (BD) / BMI >30 kg/m2 / Metabolic Syndromes / Schizoaffective Disorders / Schizophrenic Disorders1
Not AvailableCompletedBasic ScienceDelayed Sleep Phase Disorder / Jet-lag / Shift-work Disorder1
Not AvailableCompletedBasic ScienceDisseminated Sclerosis / Oxidative Stress1
Not AvailableCompletedBasic SciencePharmacokinetics of Melatonin1
Not AvailableCompletedBasic ScienceVasospastic Syndrome1
Not AvailableCompletedSupportive CareConfusion and disorientation / Delirium / Postoperative pain / Sleep1
Not AvailableCompletedTreatmentBlindness1
Not AvailableCompletedTreatmentTardive Dyskinesia1
Not AvailableCompletedTreatmentBone destruction1
Not AvailableRecruitingTreatmentPolycystic Ovaries Syndrome1
Not AvailableTerminatedTreatmentCachexia / Cancer, Advanced1
Not AvailableUnknown StatusBasic ScienceSleep Disorders, Circadian Rhythm1
Not AvailableUnknown StatusDiagnosticBlindness1
Not AvailableUnknown StatusTreatmentBlindness2
Not AvailableUnknown StatusTreatmentBlindness / Daytime Sleepiness / Sleeplessness1
Not AvailableUnknown StatusTreatmentBlindness / Sleep Disorder1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Tablet, extended releaseOral2 mg
TabletOral
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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 / Anisole / Alkyl aryl ether / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Propargyl-type 1,3-dipolar organic compound / Ether / Carboximidic acid derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
acetamides, tryptamines (CHEBI:16796 ) / Indole alkaloids, Melatonin (C01598 ) / a small molecule (N-ACETYL-5-METHOXY-TRYPTAMINE )

Targets

Kind
Protein
Organism
Human
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. [PubMed:19463840 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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. [PubMed:15992934 ]
  4. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [PubMed:19449447 ]
  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. [PubMed:20827520 ]
  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. [PubMed:20674373 ]
  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. [PubMed:19966183 ]
Kind
Protein
Organism
Human
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. [PubMed:19463840 ]
  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. [PubMed:15992934 ]
  3. Hardeland R: Melatonin: signaling mechanisms of a pleiotropic agent. Biofactors. 2009 Mar-Apr;35(2):183-92. doi: 10.1002/biof.23. [PubMed:19449447 ]
  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. [PubMed:20827520 ]
  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. [PubMed:20674373 ]
  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. [PubMed:19966183 ]
Kind
Protein
Organism
Human
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. [PubMed:15229223 ]
  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. [PubMed:19796047 ]
Kind
Protein
Organism
Human
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. [PubMed:7961794 ]
Kind
Protein
Organism
Human
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. [PubMed:15229223 ]
  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. [PubMed:19463840 ]
Kind
Protein
Organism
Human
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. [PubMed:18237195 ]
Kind
Protein
Organism
Human
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. [PubMed:18516076 ]
Kind
Protein
Organism
Human
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. [PubMed:19449447 ]
  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. [PubMed:12603316 ]
Kind
Protein
Organism
Human
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. [PubMed:180879 ]
Kind
Protein
Organism
Human
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. [PubMed:19463840 ]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:19919601 ]
  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. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [PubMed:19919601 ]
  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. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. 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. [PubMed:15626586 ]
Kind
Protein
Organism
Human
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. [PubMed:19919601 ]
  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. [PubMed:15616152 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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. [PubMed:17003850 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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. [PubMed:20167001 ]
Kind
Protein
Organism
Human
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. [PubMed:180879 ]
Kind
Protein
Organism
Human
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. [PubMed:15636586 ]
Kind
Protein
Organism
Human
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. [PubMed:15636586 ]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:12358729 ]
  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. [PubMed:10224140 ]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:51