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A3480

Sigma-Aldrich

Atosiban

≥98% (HPLC)

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

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

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This Item
SML0246SML0271SML1994
Atosiban ≥98% (HPLC)

Sigma-Aldrich

A3480

Atosiban

VER-155008 ≥98% (HPLC)

Sigma-Aldrich

SML0271

VER-155008

Sigma-Aldrich

Sigma-Aldrich

SML1994

BOP

form

lyophilized powder

form

powder

form

powder

form

powder

storage condition

desiccated

storage condition

desiccated

storage condition

desiccated

storage condition

desiccated

color

white

color

white to beige

color

white to light brown

color

white to beige

solubility

H2O: ≤100 mg/mL

solubility

DMSO: >12 mg/mL at warmed to 60 °C

solubility

DMSO: >10 mg/mL

solubility

H2O: 2 mg/mL, clear (warmed)

originator

Ferring

originator

-

originator

-

originator

-

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


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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
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)
Peter Husslein
Acta obstetricia et gynecologica Scandinavica, 81(7), 633-641 (2002-08-23)
The incidence of preterm birth has remained unchanged for the last few decades. This is due, in part, to the complex etiology of preterm labor, and the limited ability of tocolytic agents to prolong pregnancy as a result of limited

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