Atosiban

Atosiban

Atosiban is a nonapeptide, desamino-oxytocin analogue, and a competitive vasopressin/oxytocin receptor antagonist (VOTra). Atosiban is indicated to delay imminent pre-term birth in pregnant adult women. Atosiban is useful in improving the pregnancy outcome of in vitro fertilization-embryo transfer (IVF-ET) in patients with repeated implantation failure (RIF). The pregnancy rate improved from zero to 43.7%.

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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

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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

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

1. Proinsulin C-peptide and insulin: Limited pattern similarities of interest in inter-peptide interactions but no C-peptide effect on insulin and IGF-1 receptor signaling

2. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate

4. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis

5. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy

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