barusiban   Click here for help

GtoPdb Ligand ID: 10890

Synonyms: C4.6,S1-cyclo[N-(3-sulfanylpropanoyl)-D-tryptophyl-L-isoleucyl-L-alloisoleucyl-L-asparaginyl-L-2-aminobutanoyl-N-methyl-L-ornithinol] | FE 200 440 [2] | FE-200440
Comment: Barusiban (FE 200440) is an oxytocin receptor antagonist [1-2,5]. It was developed by Ferring Pharmaceuticals as a tocolytic agent, to counteract oxytocin-induced myometrial contractions [4]. Chemically it is a synthetic cyclic hexapeptide containing five unnatural amino acids and only one D-amino acid.
2D Structure
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Canonical SMILES NCCC[C@H](N(C(=O)[C@@H]1CCSCCC(=O)N[C@H](Cc2c[nH]c3c2cccc3)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)[C@@H](CC)C)[C@H](CC)C)C)CO
Isomeric SMILES NCCC[C@H](N(C(=O)[C@@H]1CCSCCC(=O)N[C@H](Cc2c[nH]c3c2cccc3)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)[C@@H](CC)C)[C@H](CC)C)C)CO
InChI InChI=1S/C40H63N9O8S/c1-6-23(3)34-38(55)46-31(20-32(42)51)36(53)45-29(40(57)49(5)26(22-50)11-10-16-41)14-17-58-18-15-33(52)44-30(19-25-21-43-28-13-9-8-12-27(25)28)37(54)47-35(24(4)7-2)39(56)48-34/h8-9,12-13,21,23-24,26,29-31,34-35,43,50H,6-7,10-11,14-20,22,41H2,1-5H3,(H2,42,51)(H,44,52)(H,45,53)(H,46,55)(H,47,54)(H,48,56)/t23-,24+,26+,29+,30-,31+,34+,35+/m1/s1
1. Gimpl G, Postina R, Fahrenholz F, Reinheimer T. (2005)
Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin.
Eur J Pharmacol, 510 (1-2): 9-16. [PMID:15740719]
2. Nilsson L, Reinheimer T, Steinwall M, Akerlund M. (2003)
FE 200 440: a selective oxytocin antagonist on the term-pregnant human uterus.
BJOG, 110 (11): 1025-8. [PMID:14592588]
3. Pierzynski P. (2011)
Oxytocin and vasopressin V(1A) receptors as new therapeutic targets in assisted reproduction.
Reprod Biomed Online, 22 (1): 9-16. [PMID:21130036]
4. Pierzynski P, Lemancewicz A, Reinheimer T, Akerlund M, Laudanski T. (2004)
Inhibitory effect of barusiban and atosiban on oxytocin-induced contractions of myometrium from preterm and term pregnant women.
J Soc Gynecol Investig, 11 (6): 384-7. [PMID:15350251]
5. Reinheimer TM, Bee WH, Resendez JC, Meyer JK, Haluska GJ, Chellman GJ. (2005)
Barusiban, a new highly potent and long-acting oxytocin antagonist: pharmacokinetic and pharmacodynamic comparison with atosiban in a cynomolgus monkey model of preterm labor.
J Clin Endocrinol Metab, 90 (4): 2275-81. [PMID:15671092]
6. Thornton S, Goodwin TM, Greisen G, Hedegaard M, Arce JC. (2009)
The effect of barusiban, a selective oxytocin antagonist, in threatened preterm labor at late gestational age: a randomized, double-blind, placebo-controlled trial.
Am J Obstet Gynecol, 200 (6): 627.e1-10. [PMID:19306963]
7. Usta IM, Khalil A, Nassar AH. (2011)
Oxytocin antagonists for the management of preterm birth: a review.
Am J Perinatol, 28 (6): 449-60. [PMID:21170825]