atosiban   Click here for help

GtoPdb Ligand ID: 2213

Synonyms: Antocin® | d[D-Tyr(Et)2,Thr4,Orn8]vasotocin | d[D-Tyr(Et)2,Thr4]OVT | ORF22164 | RWJ 22164 | Tractocile®
Approved drug
atosiban is an approved drug (EMA (2000))
Comment: A synthetic analogue of oxytocin. There is some ambiguity over the exact stereochemistry of atosiban. Another representation is CID 68613.
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2D Structure
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Isomeric SMILES NCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSCCC(=O)N[C@H](Cc2ccc(cc2)OCC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)[C@H](O)C)[C@H](CC)C
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
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Receptor binding of oxytocin and vasopressin antagonists and inhibitory effects on isolated myometrium from preterm and term pregnant women.
Br J Obstet Gynaecol, 106 (10): 1047-53. [PMID:10519430]
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Pharmacology of (2S,4Z)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino) -1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide, a new potent and selective nonpeptide antagonist of the oxytocin receptor.
J Pharmacol Exp Ther, 306 (1): 253-61. [PMID:12660315]
3. Gimpl G, Fahrenholz F. (2001)
The oxytocin receptor system: structure, function, and regulation.
Physiol Rev, 81 (2): 629-83. [PMID:11274341]
4. Jasper JR, Harrell CM, O'Brien JA, Pettibone DJ. (1995)
Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells.
Life Sci, 57 (24): 2253-61. [PMID:7475979]
5. Manning M, Cheng LL, Stoev S, Wo NC, Chan WY, Szeto HH, Durroux T, Mouillac B, Barberis C. (2005)
Design of peptide oxytocin antagonists with strikingly higher affinities and selectivities for the human oxytocin receptor than atosiban.
J Pept Sci, 11 (10): 593-608. [PMID:15880385]
6. Serradeil-Le Gal C, Valette G, Foulon L, Germain G, Advenier C, Naline E, Bardou M, Martinolle J-P, Pouzet B, Raufaste D, Garcia C, Double-Cazenave E, Pauly M, Pascal M, Barbier A, Scatton B, Maffrand J-P, Le Fur G. (2004)
SSR126768A (4-Chloro-3-[(3R)-(+)-5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2oxo-2,3-dihydro-1H-indol-3-yl]-N-ethyl-N-(3-pyridylmethyl)-benzamidine, hydrochloride): a new selective and orally active oxytocin receptor antagonist for the prevention of preterm labor.
J Pharmacol Exp Therap, 309: 414-424. [PMID:14722330]