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vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(o- methyl-l-tyrosine)-8-l-arginine-

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Description

vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(O- methyl-L-tyrosine)-8-L-arginine-: highly potent antagonist of vasopressor response to arginine-vasopressin; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9833460
CHEMBL ID2370569
MeSH IDM0083957

Synonyms (44)

Synonym
skf-100273
sk&f-100273
d(ch2)5tyr(me)avp
d(ch2)5-tyr(me)argipressin
d(ch2)5(tyr(me)(2))avp
aavp
avpa
vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(o-methyl-l-tyrosine)-8-l-arginine-
argipressin, (beta-mercapto)beta,beta-cyclopentamethylenepropionic acid(1)-o-methyl-tyr(2)-
arginine vasopressin, beta-mercapto-(beta,beta-cyclopentamethylenepropionic acid)(1)-methyl-tyr(2)-
(d(ch2)5(1)-o-me-tyr(2)-arg(8))vasopressin
1-(beta mercapto-beta,beta-cyclopentamethylenepropionic acid)-2-o-methyltyrosyl-8-arginine vasopressin
cgp-25838
sk&f 100273
cgp 25838
skf 100273
mcppa-avp
glycinamide, n-((1-mercaptocyclohexyl)acetyl)-o-methyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-arginyl-, cyclic (1-5)-disulfide
1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)-2-o-methyltyrosyl-8-arginine vasopressin
manning compound
1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)-2-(o-methyl-tyr)-argipressin
(beta-mercapto-beta,beta-cyclopentamethylene-propionyl(sup 1),o-me-tyr(sup 2),arg(sup 8))-vasopressin
cpg 25838e
73168-24-8
sigma v-2255
(beta-mercapto-beta,beta-cyclopentamethylenepropionyl(1),o-me-tyr(2),arg(8))-vasopressin
v2255 peptide
vasopressin, 1-(1-mercaptocyclohexaneacetic acid)-2-(o- methyl-l-tyrosine)-8-l-arginine-
CHEMBL2370569 ,
ffm269698k ,
unii-ffm269698k
((1-(.beta.-mercapto-.beta.,.beta.-cyclopentamethylene propionic acid), 2-(o-methyl)tyrosine))arginine vasopressin
(d(ch2)51,tyr(me)2,arg8)-vasopressin
AKOS024457591
[beta-mercapto-beta,beta-cyclopentamethylenepropionyl1, o-me-tyr2, arg8]-vasopressin, >=97% (hplc)
bdbm50155249
3-mercapto-3-methyl-butyryl-tyr(me)-phe-gln-asn-cys-pro-arg-gly-nh2
(2s)-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[(10r,13s,16s,19s,22s)-13-(2-amino-2-oxoethyl)-16-(3-amino-3-oxopropyl)-19-benzyl-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-7,8-dithia-11,14,17,20,23-pen
Q27277960
PD079483
glycinamide, 1-[[(10r,13s,16s,19s,22s)-13-(2-amino-2-oxoethyl)-16-(3-amino-3-oxopropyl)-22-[(4-methoxyphenyl)methyl]-12,15,18,21,24-pentaoxo-19-(phenylmethyl)-7,8-dithia-11,14,17,20,23-pentaazaspiro[5 .19]pentacos-10-yl]carbonyl]-l-prolyl-l-arginyl-?
DTXSID601034755
CS-0028694
HY-P1162

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
", ip) indicate that the liver is the primary site of biotransformation of the compound, suggesting that both 22a and its metabolite(s) are active, compensating probably low bioavailability of the parent molecule."( Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.
Bednarski, M; Gunia-Krzyżak, A; Marona, H; Nitek, W; Pękala, E; Powroźnik, B; Słoczyńska, K; Walczak, M; Waszkielewicz, AM; Żesławska, E, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" The AVP antagonist in the reduced dosage given alone had no effect on hormone levels."( The role of vasopressin in the nicotine-induced stimulation of ACTH and cortisol in men.
Bähr, V; Hader, O; Hensen, J; Oelkers, W; Scherer, G; Stalke, J,
)
0.13
"Intra-arterially infused arginine vasopressin (AVP) elevated systemic blood pressure (BP) in the Sprague-Dawley rat according to a dose-response pattern while cochlear blood flow (CoBF), as measured by laser Doppler flowmetry, was elevated only at the highest dose."( The influence of intra-arterial infusion of arginine vasopressin on cochlear blood flow in the rat.
Coleman, JK; Dengerink, HA; McLaren, GM; Quirk, WS; Wright, JW, 1991
)
0.28
" Cumulative dose-response curves were generated for KCl (5-100 mM), NE (10(-10)-10(-5) M), AVP, and AVT (both 10(-10)-10(-6) M) in the presence and absence of a selective V1 vasopressinergic inhibitor, [1-(beta-mercapto-beta,beta-cyclopentamethylenepropionic acid), 2-(O-methyl)tyrosine]arginine vasopressin ([d(CH2)5Tyr(Me)]AVP)."( Ontogeny of vasoconstrictor neurohypophysial hormone function in rats.
Balaraman, V; Claybaugh, JR; Ichimura, WM; Kullama, LK; Nakamura, KT, 1990
)
0.28
" In a separate group of conscious rats, it was determined that AVPRA (1-100 mg/kg/hr) produced a dose-dependent, parallel and rightward shift in the AVP vasopressor dose-response curve: the highest dose of AVPRA (i."( Effect of a selective V1 vasopressin receptor antagonist on the sequelae of endotoxemia in the conscious rat.
Egan, JW; Jugus, M; Kinter, LB; Lee, K; Smith, EF, 1989
)
0.28
" Calculation of the ED50 data from dose-response curves of both peptides show that AVP is about 10(4)-fold more active than OXT in inhibiting in vitro progesterone and androstenedione secretion."( Inhibitory effect of oxytocin and vasopressin on steroid release by cultured porcine luteal cells.
Jarry, H; Pitzel, L; Probst, I; Wuttke, W, 1988
)
0.27
" A dose-response curve to NE, ANG II, and lysine vasopressin was also performed."( Angiotensin II, vasopressin, and sympathetic activity in conscious rats with endotoxemia.
Brunner, HR; Nussberger, J; Schaller, MD; Waeber, B, 1985
)
0.27
" The antagonist dPVDAVP shifted the dose-response curves to the right without changing their slope."( Hemodynamic effects of antagonists of the vasoconstrictor action of vasopressin in conscious dogs.
Liard, JF; Spadone, JC,
)
0.13
" To test the agent's capacity to block the pressor action of exogenous AVP In humans, we constructed a dose-response curve with AVP doses of 1 to 20 mU/kg, raising BP by up to 30 mm Hg."( Effects of a specific inhibitor of the vascular action of vasopressin in humans.
Gavras, H; Gavras, I; Kohlmann, O; Mulinari, RA; Ramos, O; Ribeiro, AB; Saragoça, M,
)
0.13
" In contrast, combined treatment with enalapril and AVPA resulted in a 36 +/- 11% decrease in blood pressure after epidural dosing (n = 6)."( Endogenous vasopressin and renin-angiotensin systems support blood pressure after epidural block in humans.
Carp, H; Garvey, D; Jayaram, A; Vadhera, R, 1994
)
0.29
" Both the time-effect and dose-response relationships of AVP-induced changes in HR and CT were biphasic."( Differential effects of centrally injected AVP on heart rate, core temperature, and behavior in rats.
De Wied, D; Diamant, M, 1993
)
0.29
" Response selectivity was further established in a dose-response study that revealed an inverted U-shaped function."( New insights into neuropeptide modulation of aggression: field studies of arginine vasotocin in a territorial tropical damselfish.
Bass, AH; Santangelo, N, 2006
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vasopressin V1a receptorHomo sapiens (human)IC50 (µMol)0.00110.00060.38352.0000AID1285668; AID1336367; AID751842; AID752206
Vasopressin V1a receptorHomo sapiens (human)Ki0.00040.00020.62357.0300AID751842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endosomeVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
endocytic vesicleVasopressin V1a receptorHomo sapiens (human)
plasma membraneVasopressin V1a receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID173439In vivo anti-vasopressor activity measured as effective dose that reduces the response to 2x units of agonist to equal the response to 1x unit1985Journal of medicinal chemistry, Oct, Volume: 28, Issue:10
Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin.
AID752206Binding affinity to human vasopressin V1a receptor by radioligand displacement assay2013Bioorganic & medicinal chemistry, May-15, Volume: 21, Issue:10
Synthesis and biological evaluation of 2-(5-methyl-4-phenyl-2-oxopyrrolidin-1-yl)-acetamide stereoisomers as novel positive allosteric modulators of sigma-1 receptor.
AID168766In vivo antidiuretic activity in rats under ethanol anesthesia.1985Journal of medicinal chemistry, Oct, Volume: 28, Issue:10
Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin.
AID197146Tested for intravenous anti-vasopressor pA2 effect in rats1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
[1-beta-Mercapto-beta,beta-cyclopentamethylenepropionic acid),2-(O-methyl)tyrosine ]argine-vasopressin and [1-beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]argine-vasopressine, two highly potent antagonists of the vasopressor response to argi
AID196974In vitro anti-oxytocic potency was evaluated in the absence of Mg2+1985Journal of medicinal chemistry, Oct, Volume: 28, Issue:10
Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin.
AID172987Tested for intravenous antidiuretic activity in rats1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
[1-beta-Mercapto-beta,beta-cyclopentamethylenepropionic acid),2-(O-methyl)tyrosine ]argine-vasopressin and [1-beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]argine-vasopressine, two highly potent antagonists of the vasopressor response to argi
AID196995In vivo anti-vasopressor activity measured as the negative logarithm of the effective dose / the estimated volume of distribution (67 mL/kg)1985Journal of medicinal chemistry, Oct, Volume: 28, Issue:10
Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin.
AID1285668Displacement of [3H]AVP from human recombinant arginine vasopressin receptor 1a expressed in CHO cells2016Bioorganic & medicinal chemistry, Apr-15, Volume: 24, Issue:8
Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.
AID1336367Displacement of [3H]AVP from human recombinant V1a receptor expressed in CHO cells measured after 60 mins by scintillation counting method2017Bioorganic & medicinal chemistry, 01-15, Volume: 25, Issue:2
Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH
AID751842Binding affinity to human vasopressin V1a receptor by radioligand displacement assay2013European journal of medicinal chemistry, May, Volume: 63Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.
AID197145Tested for intravenous anti-oxytocic effect in the presence of Mg2+ in rats1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
[1-beta-Mercapto-beta,beta-cyclopentamethylenepropionic acid),2-(O-methyl)tyrosine ]argine-vasopressin and [1-beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]argine-vasopressine, two highly potent antagonists of the vasopressor response to argi
AID196975In vitro anti-oxytocic potency was evaluated in the presence of 0.5 mM of Mg2+1985Journal of medicinal chemistry, Oct, Volume: 28, Issue:10
Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin.
AID197019Tested for intravenous anti-oxytocic effect in in vivo in rats1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
[1-beta-Mercapto-beta,beta-cyclopentamethylenepropionic acid),2-(O-methyl)tyrosine ]argine-vasopressin and [1-beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]argine-vasopressine, two highly potent antagonists of the vasopressor response to argi
AID197142Tested for intravenous anti-oxytocic effect in the absence of Mg2+ in rats1980Journal of medicinal chemistry, Apr, Volume: 23, Issue:4
[1-beta-Mercapto-beta,beta-cyclopentamethylenepropionic acid),2-(O-methyl)tyrosine ]argine-vasopressin and [1-beta-mercapto-beta,beta-cyclopentamethylenepropionic acid)]argine-vasopressine, two highly potent antagonists of the vasopressor response to argi
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (346)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990143 (41.33)18.7374
1990's127 (36.71)18.2507
2000's47 (13.58)29.6817
2010's28 (8.09)24.3611
2020's1 (0.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.31

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 Index8.31 (24.57)
Research Supply Index5.89 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.31)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (1.40%)5.53%
Reviews3 (0.84%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other349 (97.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]