Atosiban

Atosiban is a peptide oxytocin receptor antagonist that helps prevent preterm labor. Buy Atosiban peptide for reproductive and uterine contractility research.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Atosiban(CAS 90779-69-4)

CAT No: 10-101-05

CAS No:90779-69-4

Synonyms/Alias:Atosiban;90779-69-4;Tractocile;Antocin;Antocin II;tractocil;Orf-22164;Antocile;Atosibanum;Rwj 22164;ORF 22164;RWJ-22164;Atosibanum [INN-Latin];CAP-476;Atosiban [USAN:INN:BAN];UNII-081D12SI0Z;1-Deamino-2D-tyr-(OEt)-4-thr-8-orn-oxytocin;DTXSID8048991;CAP-449;CAP-581;081D12SI0Z;ATOSIBAN [USAN];ATOSIBAN [INN];ATOSIBAN [MI];ATOSIBAN [MART.];(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;ATOSIBAN [WHO-DD];RW-22164;d[D-Tyr(Et)2,Thr4]OVT;1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin;CHEMBL382301;DTXCID4028917;F-314;dTVT;ORF22164;d[D-Tyr(Et)2,Thr4,Orn8]vasotocin;1-(3-Mercaptopropionic acid)-2-(3-(p-ethoxyphenyl)-D-alanine)-4-L-threonine-8-L-ornithineoxytocin;NCGC00165718-01;Atosibanum (INN-Latin);ATOSIBAN (MART.);Oxytocin, 1-(3-mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithine-;d(D-Tyr(Et)2,Thr4)OVT;d(D-Tyr(Et)2,Thr4,Orn8)vasotocin;(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-(1-hydroxyethyl)-6,9,12,15,18-pentaoxo1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;GLYCINAMIDE, O-ETHYL-N-(3-MERCAPTO-1-OXOPROPYL)-D-TYROSYL-L-ISOLEUCYL-L-THREONYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-ORNITHYL-, CYCLIC (1->5)-DISULFIDE;Tractocile (TN);Atosiban?;MFCD00672436;deTVT;(2S)-N-((2S)-5-amino-1-((2-amino-2-oxoethyl)amino)-1-oxopentan-2-yl)-1-((4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-((2S)-butan-2-yl)-16-((4-ethoxyphenyl)methyl)-10-((1R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide;(2S)-N-((2S)-5-amino-1-((2-amino-2-oxoethyl)amino)-1-oxopentan-2-yl)-1-((4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-((2S)-butan-2-yl)-16-((4-ethoxyphenyl)methyl)-10-(1-hydroxyethyl)-6,9,12,15,18-pentaoxo1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide;1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin;1-deamino-2-Tyr(OEt)-4-Thr-8-Orn-oxytocin;(Mpa(1),D-Tyr(Et)2,Thr(4),Orn(8))oxytocin;SCHEMBL34316;(Mpa(1)-D-Tyr(Et)(2)-Thr(4)-Orn(8))-oxytocin;ChEMBL_332615;GTPL2213;Atosiban, >=98% (HPLC);oxytocin, 1-deamino-(O-Et-Tyr)(2)-Thr(4)-Orn(8)-;EX-A7437A;CAP-440;G02CX01;CHEBI:135899;VWXRQYYUEIYXCZ-OBIMUBPZSA-N;oxytocin, 1-deamino-O-ethyltyrosyl(2)-threonyl(4)-ornithine(8)-;Tox21_113474;BDBM50177595;AKOS015994643;CCG-270604;DB09059;HS-2003;RW22164;RWJ22164;NCGC00165718-02;DA-59548;CAS-90779-69-4;C77085;(Deamino-Cys1,D-Tyr(Et)2,Thr4,Orn8)-Oxytocin acetate salt;(2S)-5-amino-2-{[(2S)-1-{[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-7-(carbamoylmethyl)-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide;

Chemical Name:(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide

Custom Peptide Synthesis
cGMP Peptide
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  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C43H67N11O12S2
M.W/Mr.
994.2
Sequence
One Letter Code:CXITNCPXG
Three Letter Code:deamino-Cys(1)-D-Tyr(Et)-Ile-Thr-Asn-Cys(1)-Pro-Orn-Gly-NH2
Appearance
Solid powder
Activity
Antagonist
Biological Activity
Potent oxytocin receptor (OTR) antagonist. Inhibits oxytocin-induced increase in Ca2+ concentration in myometrial cells in vitro (IC50 = 5 nM) Activates NF-κB and MAPK pathways in human amnion via Gαi signaling, resulting in pro-inflammatory effects. Inhibits oxytocin-induced uterine contractions in vivo and in vitro. Effective in a rat preterm labor model.
Target
Oxytocin Receptor

Atosiban, a synthetic peptide and oxytocin/vasopressin receptor antagonist, is widely recognized for its ability to modulate uterine contractility by selectively inhibiting oxytocin and vasopressin-mediated signaling pathways. Structurally, this compound is characterized by a modified cyclic peptide backbone, which enhances its receptor affinity and stability in biological systems. Its unique pharmacological profile allows Atosiban to act as a competitive inhibitor, effectively blocking the interaction of endogenous ligands with their respective receptors. This mechanism underpins its utility in a variety of research and experimental settings, making it a valuable tool for scientific investigations into reproductive biology, cellular signaling, and hormone-mediated processes. As a research-grade compound, Atosiban is designed for use in controlled laboratory environments, where its effects on cellular and tissue models can be precisely studied and quantified.

Reproductive Physiology Research: Atosiban is extensively used in studies focused on the regulation of uterine contractility and the molecular mechanisms underlying parturition. By antagonizing oxytocin and vasopressin receptors, this peptide allows researchers to dissect the specific contributions of these hormones to myometrial contraction and relaxation. Experimental models utilizing Atosiban can elucidate the signaling cascades involved in labor onset, providing valuable insights into the temporal dynamics of uterine activity. Such investigations are critical for advancing our understanding of reproductive physiology and the factors that govern gestational timing and fetal development.

Cellular Signaling Pathway Elucidation: The utility of this oxytocin/vasopressin antagonist extends to the exploration of intracellular signaling networks. By inhibiting G protein-coupled receptor activity, Atosiban enables the study of downstream effectors such as phospholipase C, inositol triphosphate, and calcium mobilization. These pathways are integral to a range of physiological responses, and the selective blockade provided by the compound offers a means to distinguish receptor-specific effects from broader hormonal influences. Researchers employ Atosiban in cell culture systems to map the molecular interactions that drive hormone-mediated cellular responses, contributing to a more nuanced understanding of signal transduction.

Vascular Research and Smooth Muscle Studies: Atosiban also serves as a valuable tool in the investigation of vasopressin and oxytocin's roles in vascular tone and smooth muscle contractility. Its receptor antagonist properties make it possible to assess the contribution of these peptides to vasoconstriction and blood flow regulation in various tissue models. Experimental protocols involving Atosiban can help delineate the interplay between hormonal signals and vascular responses, offering insights that are relevant to cardiovascular research and the study of smooth muscle physiology.

Endocrine System Investigations: The application of Atosiban in endocrine research is driven by its capacity to modulate peptide hormone signaling. By interfering with the binding of oxytocin and vasopressin to their receptors, this compound aids in the characterization of hormonal feedback loops and regulatory mechanisms within the hypothalamic-pituitary axis. Its use in in vitro and ex vivo systems supports the identification of receptor-specific effects on hormone secretion, receptor desensitization, and cross-talk between signaling pathways. Such studies are foundational for advancing knowledge of endocrine system function and its integration with other physiological processes.

Neurobiology and Behavioral Science: Atosiban's antagonistic action on central oxytocin and vasopressin receptors has prompted its use in neurobiological and behavioral research. Investigators utilize this molecule to probe the influence of these neuropeptides on social behavior, stress response, and emotional regulation in animal models. By selectively blocking receptor-mediated signaling, Atosiban facilitates the examination of neurochemical pathways implicated in social cognition, affiliative behaviors, and the modulation of anxiety-related responses. These applications are instrumental in unraveling the complex neuroendocrine mechanisms that underlie behavior and mental health.

In summary, Atosiban stands out as a versatile and scientifically significant tool for researchers exploring the multifaceted roles of oxytocin and vasopressin in physiological and cellular contexts. Whether employed in reproductive physiology, signaling pathway analysis, vascular studies, endocrine investigations, or neurobiological research, it provides a targeted means to manipulate and study critical hormone-mediated processes. Its receptor selectivity and well-characterized mechanism of action ensure that Atosiban remains a cornerstone compound in experimental design, supporting the advancement of knowledge across diverse fields of biological science.

Source#
Synthetic
Shipping Condition
Room temperature in continental US; may vary elsewhere.
InChI
InChI=1S/C43H67N11O12S2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1
InChI Key
VWXRQYYUEIYXCZ-OBIMUBPZSA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCCC3C(=O)NC(CCCN)C(=O)NCC(=O)N)CC(=O)N)C(C)O
Isomeric SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@@H](C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)[C@@H](C)O

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