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
The extracorporeal perfusion of the swine uterus as an experimental model: The effect of tocolytic drugs.	2006-05-01	16202502
Oxytocin stimulates secretory processes in lactating rabbit mammary epithelial cells.	2006-01-01	16166151
Visual compatibility of atosiban acetate with four drugs.	2005-12-01	16303899
Does insulin release kinins in rats?	2005-11-21	16297383
2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 2. Synthesis, chirality, and pharmacokinetics.	2005-11-03	16250654
Pharmacokinetic interaction studies of atosiban with labetalol or betamethasone in healthy female volunteers.	2005-11	16225568
Atosiban and nifedipin for the treatment of preterm labor.	2005-10	16043178
Design of peptide oxytocin antagonists with strikingly higher affinities and selectivities for the human oxytocin receptor than atosiban.	2005-10	15880385
Synthesis of oxytocin analogues with replacement of sulfur by carbon gives potent antagonists with increased stability.	2005-09-30	16277299
Possible neural mediation of the central effects of oxytocin on uterine motility.	2005-09	16105822
Oxytocin mediates the estrogen-dependent contractile activity of endothelin-1 in human and rabbit epididymis.	2005-08	15860558
Oxytocin receptor antagonists for inhibiting preterm labour.	2005-07-20	16034931
Tocolysis with atosiban: experience in the management of premature labor before 24 weeks of pregnancy.	2005-06	15909190
The oxytocin receptor antagonist atosiban inhibits cell growth via a "biased agonist" mechanism.	2005-04-22	15705593
[Tocolysis by first intention with atosiban].	2005-04	15894214
[Licensed or non-licensed tocolysis?].	2005-04	15894213
Acute tocolysis.	2005-04	15758607
Barusiban, a new highly potent and long-acting oxytocin antagonist: pharmacokinetic and pharmacodynamic comparison with atosiban in a cynomolgus monkey model of preterm labor.	2005-04	15671092
[Pharmacoeconomic assessment of two tocolysis protocols for the inhibition of premature delivery].	2005-03-19	15773798
Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin.	2005-03-07	15740719
Identification, localization and functional in vitro and in vivo activity of oxytocin receptor in the rat penis.	2005-03	15749815
Maintenance tocolysis.	2005-03	15715609
Tocolytic therapy and clinical experience. Combination therapy.	2005-03	15715603
Adverse effects of tocolytic therapy.	2005-03	15715600
Inhibition of trigemino-hypoglossal reflex in rats by oxytocin is mediated by mu and kappa opioid receptors.	2005-02-21	15713278
Oxytocin microinjected into dorsal motor nucleus of the vagus excites gallbladder motility via NMDA receptor-NO-cGMP pathway.	2005-01-25	15680949
Ontogenesis and functional aspects of oxytocin and vasopressin gene expression in the thymus network.	2005-01	15589039
Current medical therapy in the prevention and treatment of preterm labour.	2004-12	15691786
Tocolysis and preterm labour.	2004-12	15534440
Evaluation of the maternal and neonatal effects of the oxytocin antagonist, atosiban, in a cross-fostering study in rats.	2004-11	15336713
Inhibitory effect of barusiban and atosiban on oxytocin-induced contractions of myometrium from preterm and term pregnant women.	2004-09	15350251
The Gordian knot of developing tocolytics.	2004-09	15350245
Recent pharmacological advances in the treatment of preterm membrane rupture, labour and delivery.	2004-09	15330729
Roles of oxytocin in spatial learning and memory in the nucleus basalis of Meynert in rats.	2004-08-15	15177929
Spinal effects of oxytocin on uterine motility in anesthetized rats.	2004-08	15044182
Preterm birth.	2004-06	15652088
Centrally administered oxytocin elicits exaggerated grooming in oxytocin null mice.	2004-06	15219775
Delaying preterm delivery at the threshold of viability.	2004-06	15203596
Emerging issues over the choice of nifedipine, beta-agonists and atosiban for tocolysis in spontaneous preterm labour--a proposed systematic review by the International Preterm Labour Council.	2004-04	15203610
Tocolysis: current controversies, future directions.	2004-04	15134284
Management options for preterm labour in Canada.	2004-04	15115623
The drugs we deserve.	2004-04	15008784
A prospective randomised trial of atosiban versus hexoprenaline for acute tocolysis and intrauterine resuscitation.	2004-04	15008765
SSR126768A (4-chloro-3-[(3R)-(+)-5-chloro-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-N-ethyl-N-(3-pyridylmethyl)-benzamide, hydrochloride): a new selective and orally active oxytocin receptor antagonist for the prevention of preterm labor.	2004-04	14722330
[Comparison of the cost of treatment of premature labor with atosiban or beta-sympathomimetics from the perspective of the health care payer--a pharmacoeconomic model].	2004-03	15141520
Sex differences and developmental effects of manipulations of oxytocin on alloparenting and anxiety in prairie voles.	2004-03	14994263
Atosiban treatment for uterine hyperactivity during active labor: a pilot study.	2004	15085889
Atosiban for preterm labour.	2004	14969573
Endogenous oxytocin excites phasic contraction of gallbladder in rabbits through oxytocin receptor.	2003-09-30	14672277
Effects of mating stimuli and oxytocin on plasma cortisol concentration in gilts.	2002-03	14666160

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