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
Compound class: Peptide or derivative
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key UGNGRKKDUVKQDF-IHOMMZCZSA-N
References
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]