{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = (4''S'',7''S'',10''S'',13''S'',16''R'')-''N''-[(2''S'')-5-Amino-1-hydroxy-2-pentanyl]-7-(2-amino-2-oxoethyl)-10-[(2''R'')-2-butanyl]-13-''sec''-butyl-16-(1''H''-indol-3-ylmethyl)-''N''-methyl-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide | image = Barusiban.svg | image_class = skin-invert-image | width = 250 | CAS_number = 285571-64-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = UX33I93GLS | ATC_prefix = None | ATC_suffix = | PubChem = 9832431 | DrugBank = | ChemSpiderID = 8008159 | chemical_formula = | C=40 | H=63 | N=9 | O=8 | S=1 | smiles = CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CCSCCC(=O)N[C@@H](C(=O)N1)CC2=CNC3=CC=CC=C32)C(=O)N(C)[C@@H](CCCN)CO)CC(=O)N)[C@H](C)CC | StdInChI = 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 | StdInChIKey = UGNGRKKDUVKQDF-IHOMMZCZSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = }}
'''Barusiban''' (INN; development code '''FE-200440''') is a non-peptide drug which is among the most potent and selective oxytocin receptor antagonists known.<ref name="LandgrafNeumann2008">{{cite book| vauthors = Landgraf R, Neumann ID |title=Advances in Vasopressin and Oxytocin - From Genes to Behaviour to Disease|url=https://books.google.com/books?id=sDRBK1y7ObEC&pg=PA489|date=10 September 2008|publisher=Elsevier|isbn=978-0-08-093247-7|pages=194,489}}</ref><ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W|title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA1278|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=1278–}}</ref> It was trialed by Ferring Pharmaceuticals as a treatment of preterm labor but failed to demonstrate effectiveness and was not pursued any further.<ref name="LandgrafNeumann2008" /><ref name="OuelletteJoyce2010">{{cite book| vauthors = Ouellette R, Joyce J |title=Pharmacology for Nurse Anesthesiology |url= https://archive.org/details/pharmacologyforn0000ouel|url-access=registration|date=25 October 2010|publisher=Jones & Bartlett Publishers|isbn=978-0-7637-8607-6|pages=[https://archive.org/details/pharmacologyforn0000ouel/page/450 450]–}}</ref>
==See also== * Atosiban * Epelsiban * L-368,899 * L-371,257 * Retosiban
==References== {{Reflist}}
{{Oxytocin and vasopressin receptor modulators}}
Category:Abandoned drugs Category:N-Acyltryptamines Category:Carboxamides Category:Oxytocin receptor antagonists Category:Sec-Butyl compounds Category:Tocolytics Category:Twenty-membered rings