Page last updated: 2024-12-08

deaminooxytocin

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Description

demoxytocin : A heterodetic cyclic peptide that is the synthetic analog of the peptide hormone oxytocin where the free amino group in the half-cystine residue is replaced by hydrogen. The mechanism of action and pharmacological properties of demoxytocin and oxytocin are similar. The drug affects the permeability of the cell membrane, increasing the content of calcium ions in smooth muscle cells, thereby increasing its contraction. It stimulates the contraction of smooth muscles of the uterus, as well as stimulating the contraction of myoepithelial cells of the mammary gland, and enhances the secretion of milk. [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]

deaminooxytocin: octa-peptide lacking free amino group on cystine residue; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID449224
CHEMBL ID439044
CHEBI ID135900
SCHEMBL ID38442
MeSH IDM0045897
PubMed CID13242839
CHEMBL ID435716
MeSH IDM0045897

Synonyms (46)

Synonym
113-78-0
1-(3-mercaptopropionic acid)-oxytocin
oda-914
demoxytocin [inn]
desaminooxytocin
demoxytocine [inn-french]
demossitocina [dcit]
sandopart
demoxitocina [inn-spanish]
demoxytocinum [inn-latin]
demoxytocin
oda 914
einecs 204-034-9
CHEBI:135900
sandopral
1-{[(4r,7s,10s,13s,16s)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2s)-butan-2-yl]-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-l-prolyl-l-leucylglycinamide
demoxytocine
demoxytocinum
demoxitocina
desamino-oxytocin
desamino oxytocin
odeax
(2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(4r,7s,10s,13s,16s)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2s)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan
CHEMBL439044 ,
oxytocin, deamino-
1-deaminooxytocin
demossitocina
2n9hm3x95f ,
unii-2n9hm3x95f
SCHEMBL38442
deaminooxytocin [mi]
1-(3-mercaptopropionic acid)oxytocin
demoxytocin [who-dd]
oxytocin, 1-(3-mercaptopropanoic acid)-
demoxytocin [mart.]
oxytocin, 1-(3-mercaptopropionic acid)-
bdbm50044676
Q5256388
DB13798
DTXSID701016964
CS-0109362
HY-P2168
deaminooxytocin
CHEMBL435716 ,
bdbm50056796
(2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(4s,7s,10s,13s,16s)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2s)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Many investigations have shown that these prostaglandins are effective, and within certain dosage schedules, safe oxytocics, even though the systemic administration is accompanied by side effects, mainly from the gastro-intestinal tract."( Labor induction with prostaglandins.
Lange, AP; Pedersen, GT; Secher, NJ; Westergaard, JG, 1983
)
0.27
" Relative to oxytocin, [5-t-BuPro(7)]oxytocin and [Mpa(1),5-t-BuPro(7)]oxytocin exhibited strongly reduced binding affinity to the receptor; however, both peptides maintained the pharmacophore characteristics responsible for signal transfer evoking the same maximal response as oxytocin in the single-dose procedure and exhibiting partial agonistic activity in the cumulative dose-response procedure."( A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
BĂ©lec, L; Lubell, WD; Slaninova, J, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
oxytocicA drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
[role 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]

Drug Classes (1)

ClassDescription
heterodetic cyclic peptideA heterodetic cyclic peptide is a peptide consisting only of amino-acid residues, but in which the linkages forming the ring are not solely peptide bonds; one or more is an isopeptide, disulfide, ester, or other bond.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Oxytocin receptorHomo sapiens (human)Ki0.00030.00010.07180.9780AID1306778
Vasopressin V1a receptorHomo sapiens (human)IC50 (µMol)10.00000.00060.38352.0000AID1178653
Oxytocin receptorRattus norvegicus (Norway rat)Ki0.00200.00090.04890.2300AID151927; AID223652
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vasopressin V2 receptorHomo sapiens (human)EC50 (µMol)0.00350.00000.55066.7000AID1178647
Oxytocin receptorHomo sapiens (human)EC50 (µMol)0.00000.00000.08050.8810AID1178646; AID1306776; AID1370595; AID1450439
Vasopressin V1a receptorHomo sapiens (human)EC50 (µMol)0.01910.00000.19713.2000AID1178648; AID1370597; AID1450440; AID1450441
Vasopressin V1b receptorHomo sapiens (human)EC50 (µMol)0.18000.00000.03600.2400AID1178649
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (69)

Processvia Protein(s)Taxonomy
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)
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 (7)

Processvia Protein(s)Taxonomy
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)
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 (11)

Processvia Protein(s)Taxonomy
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)
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 (65)

Assay IDTitleYearJournalArticle
AID1151058Antidiuretic activity in rat1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Oxytocin analogues with combined high smooth muscle and negligible antidiuretic activities. Investigation of position 7 in neurohypophyseal hormones.
AID1178651Selectivity ratio of EC50 for human vasopressin V1a expressed in HEK293 cells to EC50 for human oxytocin receptor expressed in CHO-K1 cells2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178647Agonist activity at human vasopressin V2 expressed in HEK293 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1370598Agonist activity at human OTR expressed in CHO cells assessed as increase in calcium flux after 60 to 120 mins by fluo-4 dye based FLIPR assay relative to control2018Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3
Hybrid peptide-small molecule oxytocin analogs are potent and selective agonists of the oxytocin receptor.
AID1178656Clearance in Sprague-Dawley rat at 0.2 mg/kg, iv administered in cassette mode as bolus dose2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1450439Agonist activity at human OTR expressed in CHO cells assessed as calcium mobilization measured after 30 mins by Fluo-4-AM dye based FLIPR assay2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Potent and selective oxytocin receptor agonists without disulfide bridges.
AID1370596Stability in human liver microsomes by LC/MS/MS analysis2018Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3
Hybrid peptide-small molecule oxytocin analogs are potent and selective agonists of the oxytocin receptor.
AID1306777Intrinsic agonist activity at human oxytocin receptor expressed in CHO cells assessed as increase in intracellular calcium flux measured for 90 sec by fluo-4 dye based FLIPR assay relative to control2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Systematic N-methylation of oxytocin: Impact on pharmacology and intramolecular hydrogen bonding network.
AID1150194Induction of vasodepressor activity in conscious chicken1976Journal of medicinal chemistry, Jul, Volume: 19, Issue:7
Synthesis and some pharmacological properties of oxytocin analogues having L-thiazolidine-4-carboxylic acid in position 7.
AID1150193Induction of oxytocic activity in rat uterus1976Journal of medicinal chemistry, Jul, Volume: 19, Issue:7
Synthesis and some pharmacological properties of oxytocin analogues having L-thiazolidine-4-carboxylic acid in position 7.
AID1151055Activity at rat oxytocin receptor in rat uterus assessed as uterotonic activity1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Oxytocin analogues with combined high smooth muscle and negligible antidiuretic activities. Investigation of position 7 in neurohypophyseal hormones.
AID1450441Agonist activity at human V1b receptor expressed in CHO cells assessed as calcium mobilization measured after 30 mins by Fluo-4-AM dye based FLIPR assay2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Potent and selective oxytocin receptor agonists without disulfide bridges.
AID1178659Partial agonist activity at human vasopressin V1a expressed in HEK293 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178646Agonist activity at human oxytocin receptor expressed in CHO-K1 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178650Selectivity ratio of EC50 for human vasopressin V2 expressed in HEK293 cells to EC50 for human oxytocin receptor expressed in CHO-K1 cells2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178648Agonist activity at human vasopressin V1a expressed in HEK293 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1450440Agonist activity at human V1a receptor expressed in CHO cells assessed as calcium mobilization measured after 30 mins by Fluo-4-AM dye based FLIPR assay2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Potent and selective oxytocin receptor agonists without disulfide bridges.
AID1450442Selectivity ratio of EC50 for human V1a receptor to EC50 for human OTR2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Potent and selective oxytocin receptor agonists without disulfide bridges.
AID1151059Pressor activity in rat1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Oxytocin analogues with combined high smooth muscle and negligible antidiuretic activities. Investigation of position 7 in neurohypophyseal hormones.
AID1178652Selectivity ratio of EC50 for human vasopressin V1b expressed in HEK293 cells to EC50 for human oxytocin receptor expressed in CHO-K1 cells2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1306778Displacement of [3H]8-arginine-vasopressin from human oxytocin receptor expressed in CHO cell membrane incubated for 1 hr by liquid scintillation counting method2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Systematic N-methylation of oxytocin: Impact on pharmacology and intramolecular hydrogen bonding network.
AID1370597Agonist activity at vasopressin 1a receptor (unknown origin)2018Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3
Hybrid peptide-small molecule oxytocin analogs are potent and selective agonists of the oxytocin receptor.
AID1151056Induction of oxytocic activity in rabbit assessed as milk ejection1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Oxytocin analogues with combined high smooth muscle and negligible antidiuretic activities. Investigation of position 7 in neurohypophyseal hormones.
AID1370595Agonist activity at human OTR expressed in CHO cells assessed as increase in calcium flux after 60 to 120 mins by fluo-4 dye based FLIPR assay2018Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3
Hybrid peptide-small molecule oxytocin analogs are potent and selective agonists of the oxytocin receptor.
AID1178649Agonist activity at human vasopressin V1b expressed in HEK293 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178653Antagonist activity at human vasopressin V1a expressed in AVP-stimulated HEK293 cells after 5 hrs by firefly luciferase reporter gene assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1178663Partial agonist activity at human vasopressin V1a expressed in HEK293 cells after 5 hrs by firefly luciferase reporter gene assay relative to control2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
New, potent, and selective peptidic oxytocin receptor agonists.
AID1151057Induction of vasodepressor activity in conscious chicken1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
Oxytocin analogues with combined high smooth muscle and negligible antidiuretic activities. Investigation of position 7 in neurohypophyseal hormones.
AID1450443Selectivity ratio of EC50 for human V1b receptor to EC50 for human OTR2017Bioorganic & medicinal chemistry letters, 06-01, Volume: 27, Issue:11
Potent and selective oxytocin receptor agonists without disulfide bridges.
AID1306776Agonist activity at human oxytocin receptor expressed in CHO cells assessed as increase in intracellular calcium flux measured for 90 sec by fluo-4 dye based FLIPR assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Systematic N-methylation of oxytocin: Impact on pharmacology and intramolecular hydrogen bonding network.
AID1150195Effect on pressor activity in rat1976Journal of medicinal chemistry, Jul, Volume: 19, Issue:7
Synthesis and some pharmacological properties of oxytocin analogues having L-thiazolidine-4-carboxylic acid in position 7.
AID230138Tested for the ratio of uterotonic potency to pressor potency(O/P)1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID176218Effective dose was evaluated for the pressor activity in the dose range 2 x 10e -5-2 x 10e -4 mg/kg of rat2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
AID151927Binding affinity against Oxytocin receptor was determined in rat uterine membrane using radioligand [3H]oxytocin1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides.
AID294434Agonist activity in rat uterus by uterotonic assay2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Synthesis and biological activity of oxytocin analogues containing conformationally-restricted residues in position 7.
AID1150413Activity at oxytocin receptor in rat uterus1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID1137271Agonist activity at oxytocin receptor (unknown origin)1979Journal of medicinal chemistry, Jan, Volume: 22, Issue:1
[1-Penicillamine,2-leucine]oxytocin. Synthesis and pharmacological and conformational studies of a potent peptide hormone inhibitor.
AID230134Tested for the ratio of uterotonic potency to antidiuretic potency(O/A)1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID1149618Antidiuretic activity in rat1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogues with L-3,4-dehydroproline in position 7.
AID1144696Agonist activity at oxytocin receptor in rat uterus1976Journal of medicinal chemistry, Feb, Volume: 19, Issue:2
Synthesis and some pharmacological properties of five analogs of oxytocin having L-homocysteine in position 6.
AID169130Biological activity was determined by pressor test using pithed rat preparations1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides.
AID1148686Vasopressor activity in iv dosed phenoxybenzamine treated rat1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Design of potent antagonists of the vasopressor response to arginine-vasopressin.
AID1150420Ratio of activity at oxytocin receptor in rat uterus to vasopressor activity in rat1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID1144698Agonist activity at oxytocin receptor in chicken by avian vasodepressor assay1976Journal of medicinal chemistry, Feb, Volume: 19, Issue:2
Synthesis and some pharmacological properties of five analogs of oxytocin having L-homocysteine in position 6.
AID171775Uterotonic activity in vitro in isolated rat uterus in absence of magnesium1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID1148688Antidiuretic activity in iv dosed rat1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Design of potent antagonists of the vasopressor response to arginine-vasopressin.
AID1150414Activity at oxytocin receptor in rat uterus in presence of 0.5 mM Mg2+1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID1149619Pressor activity in rat1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogues with L-3,4-dehydroproline in position 7.
AID1149616Activity at uterotonic receptor in rat uterus assessed as uterotonic activity1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogues with L-3,4-dehydroproline in position 7.
AID190050In Vitro evaluation for the uterotonic activity in rat in the absence of Magnesium2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
AID168538Tested for vasopressor activity in rat1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID1150417Oxytocic activity in rabbit assessed as milk ejection1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID190022Compound was evaluated for the pressor activity2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
AID1150419Antidiuretic activity in rat1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID169132Biological activity was determined by uterotonic in vitro test in magnesium-free solution1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides.
AID223652Binding affinity against oxytocin receptor2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
AID294437Antagonist activity in phenoxybenzamine-treated rat by Pressor assay2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Synthesis and biological activity of oxytocin analogues containing conformationally-restricted residues in position 7.
AID190051In Vitro evaluation for the uterotonic activity in rat in the presence of 1 mM of Magnesium2000Journal of medicinal chemistry, Apr-20, Volume: 43, Issue:8
A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population.
AID1150418Vasopressor activity in rat1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID1144700Agonist activity at oxytocin receptor in rat assessed as pressor response1976Journal of medicinal chemistry, Feb, Volume: 19, Issue:2
Synthesis and some pharmacological properties of five analogs of oxytocin having L-homocysteine in position 6.
AID169134Biological activity was determined by uterotonic in vivo test using urethane-anesthetized rats (protracted action)1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides.
AID1150421Ratio of activity at oxytocin receptor in rat uterus to antidiuretic activity in rat1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-
AID168372Tested for antidiuretic activity in rat1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID171590The compound was tested for milk ejection activity in rat1983Journal of medicinal chemistry, Apr, Volume: 26, Issue:4
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
AID1149617Vasodepressor activity in fowl1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Pharmacological effects of introducing a double bond into a binding site of oxytocin. Analogues with L-3,4-dehydroproline in position 7.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-199034 (75.56)18.7374
1990's3 (6.67)18.2507
2000's3 (6.67)29.6817
2010's5 (11.11)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.38

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.38 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials3 (6.98%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
Other40 (93.02%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]