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A3480

Atosiban

Name: Atosiban
Brand: SIGMA

≥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

UNSPSC Code:

51111800

PubChem Substance ID:

24724390

NACRES:

NA.77

MDL number:

MFCD00672436

Assay:

≥98% (HPLC)

Form:

lyophilized powder

Quality level:

100

Storage condition:

desiccated

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Product Name

Atosiban, ≥98% (HPLC)

Quality Level

100

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

Bioactive Small Molecules

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 (Oxtr^PBN)

Biochem/physiol Actions

Atosiban is a peptide oxytocin receptor antagonist.

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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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An oxytocin receptor antagonist (atosiban) in the treatment of preterm labor: a randomized, double-blind, placebo-controlled trial with tocolytic rescue

Romero R, et al.

American Journal of Obstetrics and Gynecology, 182(5), 1173-1183 (2000)

Oxytocin regulates changes of extracellular glutamate and GABA levels induced by methamphetamine in the mouse brain.

Jia Qi et al.

Addiction biology, 17(4), 758-769 (2012-04-18)

Oxytocin (OT), a neurohypophyseal neuropeptide, affects adaptive processes of the central nervous system. In the present study, we investigated the effects of OT on extracellular levels of glutamate (Glu) and γ-aminobutyric acid (GABA) induced by methamphetamine (MAP) in the medial

Tocolytic therapy for preterm delivery: systematic review and network meta-analysis.

David M Haas et al.

BMJ (Clinical research ed.), 345, e6226-e6226 (2012-10-11)

To determine the most effective tocolytic agent at delaying delivery. Systematic review and network meta-analysis. Cochrane Central Register of Controlled Trials, Medline, Medline In-Process, Embase, and CINAHL up to 17 February 2012. Randomised controlled trials of tocolytic therapy in women

Oxytocin hyperpolarizes cultured duodenum myenteric intrinsic primary afferent neurons by opening BK(Ca) channels through IP₃ pathway.

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

Atosiban, an oxytocin receptor blocking agent: pharmacokinetics and inhibition of milk ejection in dairy cows.

O Wellnitz et al.

The Journal of dairy research, 66(1), 1-8 (1999-04-07)

Plasma concentrations of the oxytocin receptor blocking agent Atosiban were measured at 2, 4, 10, 15 and 20 min after injection of 5, 10, 20 and 50 micrograms Atosiban/kg body weight in six dairy cows. The half life of Atosiban

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