Compounds > epelsiban
Page last updated: 2024-11-12

epelsiban

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Description

epelsiban: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11634973
CHEMBL ID2037511
CHEBI ID177448
SCHEMBL ID1597672
MeSH IDM0572512

Synonyms (35)

Synonym
872599-83-2
CHEBI:177448
epelsiban
(3r,6r)-6-[(2s)-butan-2-yl]-3-(2,3-dihydro-1h-inden-2-yl)-1-[(1r)-1-(2,6-dimethylpyridin-3-yl)-2-morpholin-4-yl-2-oxoethyl]piperazine-2,5-dione
D10117
epelsiban (usan)
bdbm50384820
3-(2,3-dihydro-1h-inden-2-yl)-1-(1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl)-6-(1-methylpropyl)-2,5-piperazinedione
(3r,6r)-3-(2,3-dihydro-1h-inden-2-yl)-1-((1r)-1-(2,6-dimethylpyridin-3-yl)-2-(morpholin- 4-yl)-2-oxoethyl)-6-((1s)-1-methylpropyl)piperazine-2,5-dione
2,5-piperazinedione, 3-(2,3-dihydro-1h-inden-2-yl)-1-((1r)-1-(2,6-dimethyl-3-pyridinyl)- 2-(4-morpholinyl)-2-oxoethyl)-6-((1s)-1-methylpropyl)-, (3r,6r)-
unii-t2ez19hx73
epelsiban [usan:inn]
t2ez19hx73 ,
gsk 557296
gsk557296
CHEMBL2037511
gsk-557296
epelsiban [who-dd]
3r,6r)-3-(2,3-dihydro-1h-inden-2-yl)-1-((1r)-1-(2,6-dimethylpyridin-3-yl)-2-(morpholin-4-yl)-2-oxoethyl)-6-((1s)-1-methylpropyl)piperazine-2,5-dione
2,5-piperazinedione, 3-(2,3-dihydro-1h-inden-2-yl)-1-((1r)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl)-6-((1s)-1-methylpropyl)-, (3r,6r)-
epelsiban [usan]
(3r,6r)-3-(2,3-dihydro-1h-inden-2-yl)-1-((1r)-1-(2,6-dimethylpyridin-3-yl)-2-(morpholin-4-yl)-2-oxoethyl)-6-((2s)-butan-2-yl)piperazine-2,5-dione
morpholine, 4-((2r)-((3r,6r)-3-(2,3-dihydro-1h-inden-2-yl)-6-((1s)-1-methylpropyl)-2,5-dioxo-1-piperazinyl)(2,6-dimethyl-3-pyridinyl)acetyl)-
epelsiban [inn]
SCHEMBL1597672
UWHCWRQFNKUYCG-QUZACWSFSA-N
(3r,6r)-3-(2,3-dihydro-1h-inden-2-yl)-1-[(1r)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl]-6-[(1s)-1-methylpropyl]-2,5-piperazinedione
HY-105018
CS-0024708
DB11934
Q5382095
(3r,6r)-6-((s)-sec-butyl)-3-(2,3-dihydro-1h-inden-2-yl)-1-((r)-1-(2,6-dimethylpyridin-3-yl)-2-morpholino-2-oxoethyl)piperazine-2,5-dione
872599-83-2 (free base)
DTXSID701029864
AKOS040733331

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Headache was the most common adverse event, and rates were similar across all groups."( Safety and efficacy of epelsiban in the treatment of men with premature ejaculation: a randomized, double-blind, placebo-controlled, fixed-dose study.
Barnes, A; Black, L; Condreay, LD; Giancaterino, L; Mahar, KM; McCallum, SW; Shinghal, R; Stier, B, 2013)		0.7

Bioavailability

ExcerptReferenceRelevance
" Epelsiban has low levels of intrinsic clearance against the microsomes of four species, good bioavailability (55%) and comparable potency to atosiban in the rat, but is 100-fold more potent than the latter in vitro and was negative in the genotoxicity screens with a satisfactory oral safety profile in female rats."( Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
Allen, MJ; Borthwick, AD; Davies, DE; Exall, AM; Hamlett, C; Hickey, DM; Liddle, J; Mason, AM; Nerozzi, F; Peace, S; Pollard, D; Pullen, MA; Smith, IE; Sollis, SL; Stanislaus, DJ; Westfall, TD; Woollard, PM, 2012)		1.29

Dosage Studied

Epelsiban was generally well tolerated. No events of clinical concern were observed in volunteers dosed in this study.

ExcerptRelevanceReference
" Epelsiban was generally well tolerated, and no events of clinical concern were observed in volunteers dosed in this study."( A single- and multiple-dose study to investigate the pharmacokinetics of epelsiban and its metabolite, GSK2395448, in healthy female volunteers.
Fries, M; Mahar, KM; McCallum, SW; Stier, B, 2015)		1.56
" In 1 study (n = 12), epelsiban was dosed at 300 or 450 mg twice daily (every 12 hours) for a single day."( Single- and Multiple-Day Dosing Studies to Investigate High-Dose Pharmacokinetics of Epelsiban and Its Metabolite, GSK2395448, in Healthy Female Volunteers.
Amrine-Madsen, H; Cooper, M; Enslin, MB; Gress, A; Mahar, KM, 2018)		1.02
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 1A2Homo sapiens (human)IC50 (µMol)100.00000.00011.774010.0000AID664091
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)100.00000.00011.753610.0000AID664095; AID664096
Cytochrome P450 2D6Homo sapiens (human)IC50 (µMol)100.00000.00002.015110.0000AID664094
Cytochrome P450 2C9 Homo sapiens (human)IC50 (µMol)100.00000.00002.800510.0000AID664092
Vasopressin V2 receptorHomo sapiens (human)Ki3.98110.00040.43453.9811AID664086
Oxytocin receptorHomo sapiens (human)IC50 (µMol)0.00920.00270.21910.5190AID1568181
Oxytocin receptorHomo sapiens (human)Ki0.00010.00010.07180.9780AID664068
Cytochrome P450 2C19Homo sapiens (human)IC50 (µMol)100.00000.00002.398310.0000AID664093
Vasopressin V1a receptorHomo sapiens (human)Ki6.30960.00020.62357.0300AID664084
Vasopressin V1b receptorHomo sapiens (human)Ki7.94330.00050.18971.7820AID664085
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (111)

Processvia Protein(s)Taxonomy
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C9 Homo sapiens (human)
steroid metabolic processCytochrome P450 2C9 Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2C9 Homo sapiens (human)
estrogen metabolic processCytochrome P450 2C9 Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2C9 Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C9 Homo sapiens (human)
urea metabolic processCytochrome P450 2C9 Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 2C9 Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C9 Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2C9 Homo sapiens (human)
amide metabolic processCytochrome P450 2C9 Homo sapiens (human)
icosanoid biosynthetic processCytochrome P450 2C9 Homo sapiens (human)
oxidative demethylationCytochrome P450 2C9 Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C9 Homo sapiens (human)
positive regulation of systemic arterial blood pressureVasopressin V2 receptorHomo sapiens (human)
renal water retentionVasopressin V2 receptorHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayVasopressin V2 receptorHomo sapiens (human)
activation of adenylate cyclase activityVasopressin V2 receptorHomo sapiens (human)
hemostasisVasopressin V2 receptorHomo sapiens (human)
positive regulation of cell population proliferationVasopressin V2 receptorHomo sapiens (human)
negative regulation of cell population proliferationVasopressin V2 receptorHomo sapiens (human)
positive regulation of gene expressionVasopressin V2 receptorHomo sapiens (human)
telencephalon developmentVasopressin V2 receptorHomo sapiens (human)
response to cytokineVasopressin V2 receptorHomo sapiens (human)
positive regulation of intracellular signal transductionVasopressin V2 receptorHomo sapiens (human)
cellular response to hormone stimulusVasopressin V2 receptorHomo sapiens (human)
positive regulation of vasoconstrictionVasopressin V2 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayVasopressin V2 receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by vasopressinVasopressin V2 receptorHomo sapiens (human)
suckling behaviorOxytocin receptorHomo sapiens (human)
response to amphetamineOxytocin receptorHomo sapiens (human)
muscle contractionOxytocin receptorHomo sapiens (human)
cell surface receptor signaling pathwayOxytocin receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationOxytocin receptorHomo sapiens (human)
heart developmentOxytocin receptorHomo sapiens (human)
lactationOxytocin receptorHomo sapiens (human)
memoryOxytocin receptorHomo sapiens (human)
response to xenobiotic stimulusOxytocin receptorHomo sapiens (human)
positive regulation of norepinephrine secretionOxytocin receptorHomo sapiens (human)
telencephalon developmentOxytocin receptorHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicOxytocin receptorHomo sapiens (human)
response to estradiolOxytocin receptorHomo sapiens (human)
response to progesteroneOxytocin receptorHomo sapiens (human)
response to anoxiaOxytocin receptorHomo sapiens (human)
response to cytokineOxytocin receptorHomo sapiens (human)
social behaviorOxytocin receptorHomo sapiens (human)
response to cocaineOxytocin receptorHomo sapiens (human)
maternal behaviorOxytocin receptorHomo sapiens (human)
sperm ejaculationOxytocin receptorHomo sapiens (human)
eating behaviorOxytocin receptorHomo sapiens (human)
response to peptide hormoneOxytocin receptorHomo sapiens (human)
estrous cycleOxytocin receptorHomo sapiens (human)
positive regulation of blood pressureOxytocin receptorHomo sapiens (human)
digestive tract developmentOxytocin receptorHomo sapiens (human)
positive regulation of synapse assemblyOxytocin receptorHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicOxytocin receptorHomo sapiens (human)
positive regulation of penile erectionOxytocin receptorHomo sapiens (human)
ERK1 and ERK2 cascadeOxytocin receptorHomo sapiens (human)
positive regulation of uterine smooth muscle contractionOxytocin receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisOxytocin receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayOxytocin receptorHomo sapiens (human)
female pregnancyOxytocin receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by vasopressinOxytocin receptorHomo sapiens (human)
positive regulation of vasoconstrictionOxytocin receptorHomo sapiens (human)
maternal process involved in parturitionOxytocin receptorHomo sapiens (human)
cellular response to hormone stimulusOxytocin receptorHomo sapiens (human)
long-chain fatty acid metabolic processCytochrome P450 2C19Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C19Homo sapiens (human)
steroid metabolic processCytochrome P450 2C19Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2C19Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C19Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C19Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C19Homo sapiens (human)
maternal aggressive behaviorVasopressin V1a receptorHomo sapiens (human)
positive regulation of systemic arterial blood pressureVasopressin V1a receptorHomo sapiens (human)
generation of precursor metabolites and energyVasopressin V1a receptorHomo sapiens (human)
activation of phospholipase C activityVasopressin V1a receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationVasopressin V1a receptorHomo sapiens (human)
negative regulation of female receptivityVasopressin V1a receptorHomo sapiens (human)
grooming behaviorVasopressin V1a receptorHomo sapiens (human)
blood circulationVasopressin V1a receptorHomo sapiens (human)
positive regulation of cell population proliferationVasopressin V1a receptorHomo sapiens (human)
positive regulation of heart rateVasopressin V1a receptorHomo sapiens (human)
positive regulation of glutamate secretionVasopressin V1a receptorHomo sapiens (human)
myotube differentiationVasopressin V1a receptorHomo sapiens (human)
calcium-mediated signalingVasopressin V1a receptorHomo sapiens (human)
telencephalon developmentVasopressin V1a receptorHomo sapiens (human)
positive regulation of cell growthVasopressin V1a receptorHomo sapiens (human)
positive regulation of prostaglandin biosynthetic processVasopressin V1a receptorHomo sapiens (human)
positive regulation of cellular pH reductionVasopressin V1a receptorHomo sapiens (human)
social behaviorVasopressin V1a receptorHomo sapiens (human)
cellular response to water deprivationVasopressin V1a receptorHomo sapiens (human)
maternal behaviorVasopressin V1a receptorHomo sapiens (human)
sperm ejaculationVasopressin V1a receptorHomo sapiens (human)
response to corticosteroneVasopressin V1a receptorHomo sapiens (human)
negative regulation of transmission of nerve impulseVasopressin V1a receptorHomo sapiens (human)
transport across blood-brain barrierVasopressin V1a receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayVasopressin V1a receptorHomo sapiens (human)
positive regulation of vasoconstrictionVasopressin V1a receptorHomo sapiens (human)
cellular response to hormone stimulusVasopressin V1a receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by vasopressinVasopressin V1a receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayVasopressin V1b receptorHomo sapiens (human)
activation of phospholipase C activityVasopressin V1b receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationVasopressin V1b receptorHomo sapiens (human)
positive regulation of phospholipase A2 activityVasopressin V1b receptorHomo sapiens (human)
regulation of cell population proliferationVasopressin V1b receptorHomo sapiens (human)
positive regulation of MAPK cascadeVasopressin V1b receptorHomo sapiens (human)
symbiont entry into host cellVasopressin V1b receptorHomo sapiens (human)
positive regulation of inositol phosphate biosynthetic processVasopressin V1b receptorHomo sapiens (human)
positive regulation of arachidonic acid secretionVasopressin V1b receptorHomo sapiens (human)
transport across blood-brain barrierVasopressin V1b receptorHomo sapiens (human)
cellular response to hormone stimulusVasopressin V1b receptorHomo sapiens (human)
regulation of systemic arterial blood pressure by vasopressinVasopressin V1b receptorHomo sapiens (human)
positive regulation of vasoconstrictionVasopressin V1b receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (40)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo sapiens (human)
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 oxygenCytochrome P450 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo sapiens (human)
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
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 oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
iron ion bindingCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid 14,15-epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid 11,12-epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
oxidoreductase activityCytochrome P450 2C9 Homo sapiens (human)
(S)-limonene 6-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
(S)-limonene 7-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
caffeine oxidase activityCytochrome P450 2C9 Homo sapiens (human)
(R)-limonene 6-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
aromatase activityCytochrome P450 2C9 Homo sapiens (human)
heme bindingCytochrome P450 2C9 Homo sapiens (human)
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 oxygenCytochrome P450 2C9 Homo sapiens (human)
vasopressin receptor activityVasopressin V2 receptorHomo sapiens (human)
protein bindingVasopressin V2 receptorHomo sapiens (human)
peptide bindingVasopressin V2 receptorHomo sapiens (human)
peptide hormone bindingOxytocin receptorHomo sapiens (human)
peptide bindingOxytocin receptorHomo sapiens (human)
vasopressin receptor activityOxytocin receptorHomo sapiens (human)
oxytocin receptor activityOxytocin receptorHomo sapiens (human)
monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
iron ion bindingCytochrome P450 2C19Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
oxidoreductase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
(S)-limonene 7-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
oxygen bindingCytochrome P450 2C19Homo sapiens (human)
enzyme bindingCytochrome P450 2C19Homo sapiens (human)
heme bindingCytochrome P450 2C19Homo sapiens (human)
(R)-limonene 6-monooxygenase activityCytochrome P450 2C19Homo sapiens (human)
aromatase activityCytochrome P450 2C19Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activityCytochrome P450 2C19Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C19Homo sapiens (human)
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 oxygenCytochrome P450 2C19Homo sapiens (human)
vasopressin receptor activityVasopressin V1a receptorHomo sapiens (human)
protein kinase C bindingVasopressin V1a receptorHomo sapiens (human)
protein bindingVasopressin V1a receptorHomo sapiens (human)
peptide hormone bindingVasopressin V1a receptorHomo sapiens (human)
V1A vasopressin receptor bindingVasopressin V1a receptorHomo sapiens (human)
peptide bindingVasopressin V1a receptorHomo sapiens (human)
vasopressin receptor activityVasopressin V1b receptorHomo sapiens (human)
protein kinase C bindingVasopressin V1b receptorHomo sapiens (human)
peptide bindingVasopressin V1b receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2C9 Homo sapiens (human)
plasma membraneCytochrome P450 2C9 Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C9 Homo sapiens (human)
cytoplasmCytochrome P450 2C9 Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C9 Homo sapiens (human)
endosomeVasopressin V2 receptorHomo sapiens (human)
endoplasmic reticulumVasopressin V2 receptorHomo sapiens (human)
Golgi apparatusVasopressin V2 receptorHomo sapiens (human)
plasma membraneVasopressin V2 receptorHomo sapiens (human)
membraneVasopressin V2 receptorHomo sapiens (human)
endocytic vesicleVasopressin V2 receptorHomo sapiens (human)
clathrin-coated endocytic vesicle membraneVasopressin V2 receptorHomo sapiens (human)
perinuclear region of cytoplasmVasopressin V2 receptorHomo sapiens (human)
plasma membraneVasopressin V2 receptorHomo sapiens (human)
plasma membraneOxytocin receptorHomo sapiens (human)
microvillusOxytocin receptorHomo sapiens (human)
adherens junctionOxytocin receptorHomo sapiens (human)
apical plasma membraneOxytocin receptorHomo sapiens (human)
plasma membraneOxytocin receptorHomo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2C19Homo sapiens (human)
plasma membraneCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C19Homo sapiens (human)
cytoplasmCytochrome P450 2C19Homo sapiens (human)
endosomeVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
endocytic vesicleVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
endosomeVasopressin V1b receptorHomo sapiens (human)
Golgi apparatusVasopressin V1b receptorHomo sapiens (human)
plasma membraneVasopressin V1b receptorHomo sapiens (human)
plasma membraneVasopressin V1b receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (43)

Assay IDTitleYearJournalArticle
AID664099Toxicity in Sprague-Dawley rat assessed as reduction in food intake at 100 mg/kg/day, po for 7 days2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664103Lipophilicity, log D of the compound at pH 7.42012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664070Clearance in rat at 5 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664086Displacement of [3H]vasopressin from human vasopressin V2 receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664108Clearance in cynomolgus monkey at 2 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664089Selectivity ratio of Ki for human oxytocin receptor to Ki human vasopressin V1b receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664090Selectivity ratio of Ki for human oxytocin receptor to Ki human vasopressin V2 receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664109Oral bioavailability in cynomolgus monkey at 2 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664085Displacement of [3H]vasopressin from human vasopressin V1b receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664107AUC in cynomolgus monkey at 2 mg/kg, po2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664110Half life in rat2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664095Inhibition of human CYP3A4 using diethoxyfluorescein as substrate2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664071Oral bioavailability in rat at 5 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664084Displacement of [3H]vasopressin from human vasopressin V1a receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664092Inhibition of human CYP2C92012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664069AUC in rat at 5 mg/kg, po2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664074Oral bioavailability in dog at 0.6 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664081Intrinsic clearance in cynomolgus monkey liver microsomes2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664105Chemical stability of the compound up to 3 months at 50 degC2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664098Toxicity in Sprague-Dawley rat assessed as reduction in body weight at 100 mg/kg/day, po for 7 days2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID1568181Antagonist activity at human OTR expressed in HEK293 cells assessed as decrease in calcium flux measured after 10 mins in presence of vasopressin by Fluo-4 dye based microplate reader based assay2019ACS medicinal chemistry letters, Jun-13, Volume: 10, Issue:6
Discovery of SHR1653, a Highly Potent and Selective OTR Antagonist with Improved Blood-Brain Barrier Penetration.
AID664096Inhibition of human CYP3A4 using 7-benzyloxyquinoline as substrate2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664068Displacement of [3H]oxytocin from human oxytocin receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664091Inhibition of human CYP1A22012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664100Toxicity in Sprague-Dawley rat assessed as adverse clinical signs at 100 mg/kg/day, po for 7 days2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664076Lipophilicity, log D of the compound by HPLC analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664093Inhibition of human CYP2C192012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664075Aqueous solubility of the compound by HPLC analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664073Clearance in dog at 0.6 mg/kg2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664101Toxicity in Sprague-Dawley rat assessed as adverse histological findings at 100 mg/kg/day, po for 7 days2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664080Intrinsic clearance in dog liver microsomes2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664072AUC in dog at 0.6 mg/kg, po2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664111Ratio of atosiban Ki to compound Ki for human oxytocin receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664082Intrinsic clearance in human liver microsomes2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664079Intrinsic clearance in rat liver microsomes2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664094Inhibition of human CYP2D62012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664097Genotoxicity in Salmonella typhimurium by high-throughput fluctuation test/mini-Ames assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664102Dissociation constant, pKa of the compound in aqueous solution2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664104Solubility of the compound in water2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664088Selectivity ratio of Ki for human oxytocin receptor to Ki for human vasopressin V1a receptor2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664077Binding affinity to human serum albumin2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664106Chemical stability of the compound in aqueous solution at pH 2 to 6 up to 7 days in presence of light2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
AID664087Reduction of oxytocin-induced uterine contraction in iv dosed rat uterine contractility model2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (85.71)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.75

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.75 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (42.86%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (57.14%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
7-hydroxy-2-n,n-dipropylaminotetralin
7-hydroxy-2-N,N-dipropylaminotetralin: RN given refers to cpd without isomeric designation		2.0810tetralins
oxytocin
Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.		2.0710heterodetic cyclic peptide;
peptide hormone		oxytocic;
vasodilator agent
gsk221149a
GSK221149A: highly selective oxytocin receptor antagonist; structure in first source		2.5320dipeptide
ConditionIndicatedRelationship StrengthStudiesTrials
Preterm Birth
[description not available]		02.2510
Premature Birth
CHILDBIRTH before 37 weeks of PREGNANCY (259 days from the first day of the mother's last menstrual period, or 245 days after FERTILIZATION).		02.2510
Ejaculatio Praecox
[description not available]		04.3911
Premature Ejaculation
The emission of SEMEN and seminal fluid during the act of preparation for sexual intercourse, i.e. before there is penetration, or shortly after penetration.		09.3911