ATOSIBAN

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H67N11O12S2
Molecular Weight	994.1924
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(NC(=O)[C@@]([H])(NC(=O)[C@@H](CC2=CC=C(OCC)C=C2)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

InChIKey=VWXRQYYUEIYXCZ-OBIMUBPZSA-N

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

HIDE SMILES / InChI

Molecular Formula	C43H67N11O12S2
Molecular Weight	994.1924
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.medicines.org.uk/emc/medicine/4297

Atosiban (brand name Tractocile) is a competitive antagonist of human oxytocin at receptor level. In rats and guinea pigs, atosiban was shown to bind to oxytocin receptors, to decrease the frequency of contractions and the tone of the uterine musculature, resulting in a suppression of uterine contractions. Atosiban was also shown to bind to the vasopressin receptor, thus inhibiting the effect of vasopressin. Tractocile is indicated to delay imminent pre-term birth in pregnant adult women with: − regular uterine contractions of at least 30 seconds duration at a rate of ≥ 4 per 30 minutes − a cervical dilation of 1 to 3 cm (0-3 for nulliparas) and effacement of ≥ 50% − a gestational age from 24 until 33 completed weeks − a normal foetal heart rate. Atosiban does not have U.S. Food and Drug Administration (FDA) approval for use in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxytocin receptor 19 Target ID: CHEMBL2049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16302826 \| https://www.ncbi.nlm.nih.gov/pubmed/7932368	Antagonist 2849		59.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Preterm birth 2 Sources: https://www.medicines.org.uk/emc/medicine/4297	Preventing		Approved 8583	Tractocile Approved Use Tractocile is indicated to delay imminent pre-term birth in pregnant adult women with: − regular uterine contractions of at least 30 seconds duration at a rate of ≥ 4 per 30 minutes − a cervical dilation of 1 to 3 cm (0-3 for nulliparas) and effacement of ≥ 50% − a gestational age from 24 until 33 completed weeks − a normal foetal heart rate Launch Date 2000

PubMed

Title	Date	PubMed
Receptor binding of oxytocin and vasopressin antagonists and inhibitory effects on isolated myometrium from preterm and term pregnant women.	1999 Oct	10519430
The oxytocin receptor system: structure, function, and regulation.	2001 Apr	11274341
Tocolysis with beta-adrenergic receptor agonists.	2001 Aug	11561912
Atosiban for the primary prevention of preterm labour.	2001 Aug	11510718
Effectiveness and safety of the oxytocin antagonist atosiban versus beta-adrenergic agonists in the treatment of preterm labour. The Worldwide Atosiban versus Beta-agonists Study Group.	2001 Feb	11236112
Effects of oxytocin receptor antagonist atosiban on pregnant myometrium in vitro.	2001 Jul	11430968
Effect of centrally administered oxytocin on gastric and duodenal ulcers in rats.	2001 Jun	11747752
Oxytocin antagonist disrupts hypotension-evoked renin secretion and other responses in conscious rats.	2001 Mar	11171655
The oxytocin antagonist atosiban versus the beta-agonist terbutaline in the treatment of preterm labor. A randomized, double-blind, controlled study.	2001 May	11328217
Adverse and beneficial effects of tocolytic therapy.	2001 Oct	11707019
Treatment of preterm labor with the oxytocin antagonist atosiban: a double-blind, randomized, controlled comparison with salbutamol.	2001 Oct	11574128
Design of oxytocin antagonists, which are more selective than atosiban.	2001 Sep	11587184
Spontaneous contractions of myometrium from humans, non-human primate and rodents are sensitive to selective oxytocin receptor antagonism in vitro.	2001 Sep	11563467
NO-induced relaxation of labouring and non-labouring human myometrium is not mediated by cyclic GMP.	2001 Sep	11522613
Oxytocin decreases carrageenan induced inflammation in rats.	2001 Sep	11514032
Inhibition of prostaglandin synthesis and its effect on uterine activity during established premature labor in sheep.	2001 Sep-Oct	11677146
Female oxytocin-deficient mice display enhanced anxiety-related behavior.	2003 Jun	12746288
Centrally administered oxytocin elicits exaggerated grooming in oxytocin null mice.	2004 Jun	15219775
Evaluation of the maternal and neonatal effects of the oxytocin antagonist, atosiban, in a cross-fostering study in rats.	2004 Nov	15336713
Recent pharmacological advances in the treatment of preterm membrane rupture, labour and delivery.	2004 Sep	15330729
Acute tocolysis.	2005 Apr	15758607
Tocolytic therapy and clinical experience. Combination therapy.	2005 Mar	15715603
Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin.	2005 Mar 7	15740719

Patents

Sample Use Guides

In Vivo Use Guide

Tractocile (Atosiban) is administered intravenously in three successive stages: an initial bolus dose (6.75 mg), performed with Tractocile 6.75 mg/0.9 ml solution for injection, immediately followed by a continuous high dose infusion (loading infusion 300 micrograms/min) of Tractocile 37.5 mg/5 ml concentrate for solution for infusion during three hours, followed by a lower dose of Tractocile 37.5 mg/5 ml concentrate for solution for infusion (subsequent infusion 100 micrograms/min) up to 45 hours. The duration of the treatment should not exceed 48 hours. The total dose given during a full course of Tractocile therapy should preferably not exceed 330.75 mg of atosiban. Intravenous therapy using the initial bolus injection should be started as soon as possible after diagnosis of pre-term labour. Once the bolus has been injected, proceed with the infusion (See Summary of Product Characteristics of Tractocile 37.5 mg/5 ml, concentrate for solution for infusion). In the case of persistence of uterine contractions during treatment with Tractocile, alternative therapy should be considered.

Route of Administration: Intravenous

In Vitro Use Guide

Atosiban had significant inhibitory effects on myometrial contractions of myometrial strips from healthy pregnant women at concentrations as low as 1 ug/mL.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:12 GMT 2025`
Record UNII	081D12SI0Z
Record Status	`FAILED`
Record Version

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Name

Type

Language

ATOSIBAN

Official Name

English

ANTOCILE

Preferred Name

English

ATOSIBAN [MI]

Common Name

English

ORF 22164

Code

English

CAP-476

Code

English

atosiban [INN]

Common Name

English

ATOSIBAN [USAN]

Common Name

English

ORF-22164

Code

English

RW-22164

Code

English

F-314

Code

English

ATOSIBAN [MART.]

Common Name

English

RWJ-22164

Code

English

TRACTOCILE

Brand Name

English

1-(3-MERCAPTOPROPIONIC ACID)-2-(3-(P-ETHOXYPHENYL)-D-ALANINE)-4-L-THREONINE-8-L-ORNITHINEOXYTOCIN

Common Name

English

ANTOCIN II

Brand Name

English

ANTOCIN

Brand Name

English

GLYCINAMIDE, O-ETHYL-N-(3-MERCAPTO-1-OXOPROPYL)-D-TYROSYL-L-ISOLEUCYL-L-THREONYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-ORNITHYL-, CYCLIC (1->5)-DISULFIDE

Systematic Name

English

OXYTOCIN, 1-(3-MERCAPTOPROPANOIC ACID)-2-(O-ETHYL-D-TYROSINE)-4-L-THREONINE-8-L-ORNITHINE-

Common Name

English

Atosiban [WHO-DD]

Common Name

English

RWJ 22164

Code

English

CAP-581

Code

English

TRACTOCIL

Brand Name

English

CAP-449

Code

English

Classification Tree Code System Code

WHO-VATC

QG02CX01