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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  • 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 is a synthetic peptide compound that functions as an oxytocin and vasopressin receptor antagonist, making it a valuable tool in biochemical and pharmacological research. Structurally, it is a cyclic nonapeptide designed to selectively inhibit the activity of oxytocin and vasopressin at their respective receptors. Its unique receptor-binding profile enables researchers to dissect the physiological and molecular roles of these neuropeptides in various biological systems. As a research-use peptide, Atosiban provides a precise means to modulate peptide-mediated signaling pathways, supporting investigations into receptor pharmacology, signal transduction, and peptide-based functional studies.

Receptor pharmacology: Atosiban is widely employed in studies aimed at elucidating the binding characteristics, selectivity, and functional responses of oxytocin and vasopressin receptors. By serving as a competitive antagonist, it allows researchers to investigate receptor-ligand interactions, receptor subtype specificity, and downstream signaling events. Such studies are fundamental for mapping the pharmacological landscape of peptide hormone receptors and for validating new targets in neuroendocrine research.

Signal transduction research: The ability of Atosiban to block oxytocin and vasopressin signaling is instrumental in dissecting the intracellular pathways activated by these hormones. In cellular and tissue-based assays, it is routinely used to assess the impact of receptor inhibition on second messenger systems such as phospholipase C activation, calcium mobilization, and MAPK pathway modulation. This facilitates a deeper understanding of the molecular mechanisms governing hormone-mediated cellular responses.

Peptide functional studies: As a synthetic peptide antagonist, Atosiban is utilized in experiments designed to probe the physiological roles of endogenous oxytocin and vasopressin. By selectively inhibiting these peptides, researchers can delineate their contributions to processes such as smooth muscle contractility, fluid balance, and social behavior in model systems. The compound's specificity and stability make it suitable for in vitro, ex vivo, and in vivo experimental paradigms where controlled modulation of peptide action is required.

Drug discovery and development: Atosiban serves as a reference compound and pharmacological tool in early-stage drug screening and lead optimization. Its well-characterized antagonist profile supports structure-activity relationship studies, competitive binding assays, and functional screening of novel oxytocin or vasopressin receptor modulators. By benchmarking new compounds against Atosiban, researchers can efficiently evaluate potency, selectivity, and efficacy, thereby accelerating the development of next-generation peptide therapeutics.

Analytical method validation: The compound is also used in the validation of bioanalytical methods for quantifying peptide antagonists and their metabolites in biological matrices. Its defined chemical structure and receptor activity make it a suitable standard in liquid chromatography-mass spectrometry (LC-MS) and immunoassay protocols. Incorporating Atosiban into analytical workflows ensures reliable detection, quantitation, and quality control in research settings focused on peptide-based drug development and pharmacokinetic studies.

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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