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Atosiban

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Atosiban, a nonapeptide, desamino-oxytocin analogue, is a competitive inhibitor of the hormones oxytocin and vasopressinv. It inhibits the oxytocin-mediated release of inositol trisphosphate from the myometrial cell membrane. It is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor. It antagonises uterine contractions and induces uterine quiescence in human pre-term labour at the recommended dosage. It was developed by Ferring Pharmaceuticals in Sweden. It is licensed in proprietary and generic forms for the delay of imminent pre-term birth in pregnant adult women.

Category
Peptide Inhibitors
Catalog number
BAT-010038
CAS number
90779-69-4
Molecular Formula
C43H67N11O12S2
Molecular Weight
994.19
Atosiban
Size Price Stock Quantity
10 mg $187 In stock
IUPAC Name
(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide
Synonyms
1-(3-Mercaptopropionic acid)-2-(3-(p-ethoxyphenyl)-D-alanine)-4-L-thre onine-8-L-ornithineoxytocin;[Mpr-D-Tyr(OEt)-Ile-Thr-Asn-Cys]-Pro-Orn-Gly-NH2;(2S)-N-[(1S)-4-Amino-1-(carbamoylmethylcarbamoyl)butyl]-1-[(4S,7S,13S,16R)-13-[(2S)-butan-2-yl]-7-(carbamoylmethyl)-16-[(4-ethoxyphenyl)methyl]-10-(1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin;Tractocile;(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;RW22164; RWJ22164
Related CAS
914453-95-5
Appearance
Solid
Purity
95%
Density
1.254±0.06 g/cm3(Predicted)
Boiling Point
1469.0±65.0°C(Predicted)
Sequence
XYITNCPXG
Storage
Store at -20°C
Solubility
Soluble in DMSO
Application
Atosiban is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor.
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/h11-14,23-24,27-31,35-36,5
InChI Key
VWXRQYYUEIYXCZ-OBIMUBPZSA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCCC3C(=O)NC(CCCN)C(=O)NCC(=O)N)CC(=O)N)C(C)O
1.Visual compatibility of atosiban acetate with four drugs.
Swart EL, van Reij EM, Lee WC, Sinjewel A. Am J Health Syst Pharm. 2005 Dec 1;62(23):2459, 2463.
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