Barusiban information

Barusiban
Clinical data
ATC code	None;
Identifiers
	IUPAC name (4S,7S,10S,13S,16R)-N-[(2S)-5-Amino-1-hydroxy-2-pentanyl]-7-(2-amino-2-oxoethyl)-10-[(2R)-2-butanyl]-13-sec-butyl-16-(1H-indol-3-ylmethyl)-N-methyl-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide;
CAS Number	285571-64-4;
PubChem CID	9832431;
ChemSpider	8008159;
UNII	UX33I93GLS;
CompTox Dashboard (EPA)	DTXSID20182771 ;
Chemical and physical data
Formula	C40H63N9O8S
Molar mass	830.06 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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; Key:UGNGRKKDUVKQDF-IHOMMZCZSA-N;

Barusiban (INN) (code name FE-200440) is a non-peptide drug which is among the most potent and selective oxytocin receptor antagonists known.^[1]^[2] It was trialed by Ferring Pharmaceuticals as a treatment of preterm labor but failed to demonstrate effectiveness and was not pursued any further.^[1]^[3]

^ ^a ^b Landgraf R, Neumann ID (10 September 2008). Advances in Vasopressin and Oxytocin - From Genes to Behaviour to Disease. Elsevier. pp. 194, 489. ISBN 978-0-08-093247-7.
^ Offermanns S, Rosenthal W (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 1278–. ISBN 978-3-540-38916-3.
^ Ouellette R, Joyce J (25 October 2010). Pharmacology for Nurse Anesthesiology. Jones & Bartlett Publishers. pp. 450–. ISBN 978-0-7637-8607-6.

[LandgrafNeumann2008-1] Landgraf R, Neumann ID (10 September 2008). Advances in Vasopressin and Oxytocin - From Genes to Behaviour to Disease. Elsevier. pp. 194, 489. ISBN 978-0-08-093247-7.

[OffermannsRosenthal2008-2] Offermanns S, Rosenthal W (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 1278–. ISBN 978-3-540-38916-3.

[OuelletteJoyce2010-3] Ouellette R, Joyce J (25 October 2010). Pharmacology for Nurse Anesthesiology. Jones & Bartlett Publishers. pp. 450–. ISBN 978-0-7637-8607-6.

Barusiban information

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Barusiban

Carbetocin

Oxytocin

Tocolytic

Vasopressin

Desmopressin

Atosiban

Oxytocin receptor agonist

Terlipressin

Oxytocin receptor

Lithium carbonate

Uterotonic

Tolvaptan

Vasopressin receptor

Vasotocin

Vasopressin receptor 1A

Mozavaptan

Conivaptan

Demeclocycline

Vasopressin receptor antagonist

Vasopressin receptor 2

Ornipressin

Clinical data

ATC code	None
Identifiers
IUPAC name (4S,7S,10S,13S,16R)-N-[(2S)-5-Amino-1-hydroxy-2-pentanyl]-7-(2-amino-2-oxoethyl)-10-[(2R)-2-butanyl]-13-sec-butyl-16-(1H-indol-3-ylmethyl)-N-methyl-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide
CAS Number	285571-64-4
PubChem CID	9832431
ChemSpider	8008159
UNII	UX33I93GLS
CompTox Dashboard (EPA)	DTXSID20182771
Chemical and physical data
Formula	C₄₀H₆₃N₉O₈S
Molar mass	830.06 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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 Key:UGNGRKKDUVKQDF-IHOMMZCZSA-N