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Key Documents

A3480

Sigma-Aldrich

Atosiban

≥98% (HPLC)

Synonym(s):

1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin, 1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin, Tractocile

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About This Item

Empirical Formula (Hill Notation):
C43H67N11O12S2
CAS Number:
Molecular Weight:
994.19
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

lyophilized powder

storage condition

desiccated

color

white

solubility

H2O: ≤100 mg/mL

originator

Ferring

shipped in

wet ice

storage temp.

−20°C

SMILES string

[H][C@]1(NC(=O)[C@@]([H])(NC(=O)[C@@H](Cc2ccc(OCC)cc2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)[C@@H](C)CC)[C@@H](C)O

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/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1

InChI key

VWXRQYYUEIYXCZ-OBIMUBPZSA-N

Gene Information

Application

Atosiban has been used:
  • as an oxytocin receptor antagonist
  • in the calcium mobilization assay for Z factor determination in uterine myometrium (UT-myo cells) and as a therapeutic agent to inhibit preterm labor
  • to inhibit the activation of oxytocin-receptor-expressing neurons in the parabrachial nucleus of mice (OxtrPBN)

Biochem/physiol Actions

Atosiban efficiently prevent preterm uterine contractions without any major cardiovascular, pulmonary or central nervous system side effects. It has potential to treat preterm labour.
Atosiban is a peptide oxytocin receptor antagonist.

Features and Benefits

This compound was developed by Ferring. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Reconstitution

Reconstitute in deionized water at not less than 100 μg/mL, which can then be diluted into aqueous vehicle of choice. Solutions may be stored at 2-8 °C for up to seven days. For extended storage, add a carrier protein of 0.1% human serum albumin or bovine serum albumin and freeze in working aliquots at −20 °C.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effectiveness and safety of the oxytocin antagonist atosiban versus beta-adrenergic agonists in the treatment of preterm labour
versus Beta-agonists, The Worldwide Atosiban and others
British Journal of Obstetrics and Gynaecology, 108(2), 133-142 (2001)
Raed Salim et al.
Obstetrics and gynecology, 120(6), 1323-1331 (2012-11-22)
To compare the tocolytic efficacy and tolerability of nifedipine with that of atosiban among pregnant women with preterm labor. Pregnant women admitted with preterm labor and intact membranes between 24 and 33 weeks 6 days of gestation, between January 2008
Vassilis Tsatsaris et al.
Drugs, 64(4), 375-382 (2004-02-19)
Oxytocin antagonists are synthetic analogues that have the nonapeptide structure of oxytocin. They act by competing with oxytocin for receptors in the myometrium. Animal experiments and pilot clinical studies have examined several agents and, of these, atosiban has been the
Plato Mak et al.
Journal of psychopharmacology (Oxford, England), 26(4), 532-542 (2011-09-06)
Oxytocin (OT) and arginine vasopressin (AVP), in their capacities as neuromodulators, are believed to play an important role in mood control, including regulation of the anxiety response. In the present study, the contributions of oxytocin and vasopressin receptor modulation to
Jens Lyndrup et al.
Expert opinion on investigational drugs, 16(6), 843-853 (2007-05-16)
Preterm birth is the major cause of neonatal mortality and morbidity in the developed world. The perfect tocolytic that is uniformly effective with complete fetomaternal safety does not exist. Tocolytic agents differ in cost, utero-specificity, safety, efficacy and whether they

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