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Merck
CN

A3480

Sigma-Aldrich

Atosiban

≥98% (HPLC), oxytocin receptor antagonist, lyophilized powder

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:
90779-69-4
Molecular Weight:
994.19
MDL number:
MFCD00672436
UNSPSC Code:
51111800
PubChem Substance ID:
24724390
NACRES:
NA.77

Key Documents

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Product Name

Atosiban, ≥98% (HPLC)

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

human ... AVPR1A(552), OXTR(5021)
rat ... Oxtr(25342)

Related Categories

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.

Preparation Note

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000191298
0000175443
0000157673
0000157673
0000156160

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T Bossmar
Journal of perinatal medicine, 26(6), 458-465 (1999-05-04)
Oxytocin is involved in the regulation of preterm and term labor but the exact effect mechanisms are not fully understood. A regulatory action by vasopressin may also exist. The concentrations of oxytocin and vasopressin V1a receptors in myometrium from pregnant
Oxytocin modulates GABA A R subunits to confer neuroprotection in stroke in vitro
Kaneko Y, et al.
Scientific reports, 6(5), 35659-35659 (2016)
Oxytocin-receptor-expressing neurons in the parabrachial nucleus regulate fluid intake
Ryan P, et al.
Nature Neuroscience, 20(12), 1722-1722 (2017)
Silvia Gutierrez et al.
Anesthesiology, 118(1), 152-159 (2012-12-20)
Physical injury, including surgery, can result in chronic pain; yet chronic pain following childbirth, including cesarean delivery in women, is rare. The mechanisms involved in this protection by pregnancy or delivery have not been explored. We examined the effect of
Tongtong Che et al.
Journal of neurochemistry, 121(4), 516-525 (2012-02-24)
Oxytocin (OT) is clinically important in gut motility and constitutively reduces duodenum contractility. Intrinsic primary afferent neurons (IPANs), whose physiological classification is as AH cells, are the 1st neurons of the peristaltic reflex pathway. We set out to investigate if
View All Related Papers

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