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#	10-101-05
Chemical Structure
CAS	90779-69-4
Synonyms/Alias	1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin, 1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin, Tractocile;(Deamino-Cys1,D-Tyr(Et)2,Thr4,Orn8)-Oxytocin; Antocin; Tractocile; RWJ 22164; RWJ22164; RWJ-22164; ORF 22164; ORF22164; ORF-22164; deTVT; dE-TVT; Atosibanum ; Atosiban; d(TVT); CAP 476
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
M.F/Formula	C43H67N11O12S2
M.W/Mr.	994.19
Sequence	One Letter Code: XYITNCPXG Three Letter Code: Mpr-D-Tyr(Et)-Ile-Thr-Asn-Cys-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

CAT#	Product Name	M.W	Molecular Formula	Inquiry
10-101-07	Buserelin Acetate	1299.48	C62H90N16O15	Inquiry
10-101-10	Deslorelin Acetate	1342.5	C66H87N17O14	Inquiry
10-101-17	Fertirelin Acetate	1166.56	C55H74N16O13	Inquiry
10-101-61	Ganirelix	1570.4	C80H113ClN18O13	Inquiry

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Source#	Synthetic
Storage	Desiccate at -20°C
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