An oxytocin receptor antagonist
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Atosiban

Item No. 20952

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclic (1→5)-disulfide O-ethyl-N-(3-mercapto-1-oxopropyl)-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-ornithyl-glycinamide
CAS Number
90779-69-4
Synonyms
  • Antocin
  • ORF 22164
  • RWJ 22164
  • Tractocile
Molecular Formula
C43H67N11O12S2
Formula Weight
994.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 14 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
223, 246, 259, 270 nm
SMILES
O=C(N[C@H](CC1=CC=C(OCC)C=C1)C(N[C@H](C(N[C@@](C(N[C@H]2CC(N)=O)=O)([H])[C@H](O)C)=O)[C@@H](C)CC)=O)CCSSC[C@@H](C(N3CCC[C@H]3C(N[C@H](C(NCC(N)=O)=O)CCCN)=O)=O)NC2=O
InChi Code
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
InChi Key
VWXRQYYUEIYXCZ-OBIMUBPZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $42

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    5 mg

    $161

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    10 mg

    $283

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    25 mg

    $602

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    Product Description

    Atosiban is a peptide analog of oxytocin (Item No. 11799) that antagonizes the human oxytocin receptor (Ki = 81 nM).1 It also binds the vasopressin V1a receptor (Ki = 3.5 nM).1 Because of its effects on the oxytocin receptor, atosiban has tocolytic actions in the acute phase of imminent preterm birth.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cirillo, R., Tos, E.G., Schwarz, M.K., et al. Pharmacology of (2S,4Z)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino) -1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide, a new potent and selective nonpeptide antagonist of the oxytocin receptor. J.Pharmacol. Exp. Ther. 306(1), 253-261 (2003).

    2. Lamont, R.F. The development and introduction of anti-oxytocic tocolytics. B. J. O. G. 110 (Suppl 20), 108-112 (2003).

    3. Moutquin, J.M., Sherman, D., Cohen, H., et al. Double-blind, randomized, controlled trial of atosiban and ritodrine in the treatment of preterm labor: a multicenter effectiveness and safety study. Am. J. Obstet. Gynecol. 182(5), 1191-1199 (2000).

    4. Romero, R., Sibai, B.M., Sanchez-Ramos, L., et al. An oxytocin receptor antagonist (atosiban) in the treatment of preterm labor: A randomized, double-blind, placebo-controlled trial with tocolytic rescue. Am. J. Obstet. Gynecol. 182(5), 1173-1183 (2000).