Responsive image

Common name


Melatonin

IUPAC name


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

SMILES


COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

Compound class


Antioxidants; Hypnotics and Sedatives; Central Nervous System Depressants; Nervous System; Psycholeptics; Melatonin Receptor Agonists; Cytochrome P-450 CYP1A2 Inhibitors; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP1A2 Inducers; Cytochrome P-450 CYP2C9 Inducers; Cytochrome P-450 CYP2C19 Inducers;

Therapeutic area


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.

Common name


Melatonin

IUPAC name


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

SMILES


COC1=CC2=C(NC=C2CCNC(C)=O)C=C1

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)

FORMULA


C13H16N2O2

Responsive image

Common name


Melatonin

IUPAC name


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

Molecular weight


232.278

clogP


2.779

clogS


-4.010

HBond Acceptor


2

HBond Donor


2

Total Polar
Surface Area


54.12

Number of Rings


2

Rotatable Bond


4

Drug ID Common name Structure CAS SMILE Frequency
FDBF00010 indole Responsive image [nH]1ccc2c1cccc2 0.0086
FDBF00015 acetamide Responsive image NC(=O)C 0.0460
FDBF00027 N-methylacetamide Responsive image N(C(=O)C)C 0.0175
FDBF00228 N-ethylacetamide Responsive image C(=O)(NCC)C 0.0089
FDBF02362 5-methoxy-1H-indole Responsive image [nH]1c2c(cc1)cc(cc2)OC 0.0003
FDBF02363 5-methoxy-3-methyl-1H-indole Responsive image [nH]1c2c(c(c1)C)cc(cc2)OC 0.0003
FDBF02364 N-[2-(1H-indol-3-yl)ethyl]acetamide Responsive image [nH]1c2c(c(c1)CCNC(=O)C)cccc2 0.0003
7 , 1