ATOSIBAN ACETATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H67N11O12S2.C2H4O2
Molecular Weight	1054.2445
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.[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=SVDWBHHCPXTODI-QIWYXCRTSA-N

InChI=1S/C43H67N11O12S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/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

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 oxytocin receptor system: structure, function, and regulation.	2001 Apr	11274341
[Tocolysis. Atosiban, an ocytcin-receptor antagonist].	2001 May	11397999
The oxytocin antagonist atosiban versus the beta-agonist terbutaline in the treatment of preterm labor. A randomized, double-blind, controlled study.	2001 May	11328217
Involvement of oxytocin and vasopressin in the pathophysiology of preterm labor and primary dysmenorrhea.	2002	12436949
Development and clinical experience with the new evidence-based tocolytic atosiban.	2002 Jul	12190838
Effects of mating stimuli and oxytocin on plasma cortisol concentration in gilts.	2002 Mar	14666160
Exploring the role of Tractocile in everyday clinical practice.	2003 Apr	12763126
The oxytocin receptor.	2003 Jul	12826328
The effects of a progesterone metabolite, 5 beta-dihydroprogesterone, on oxytocin receptor binding in human myometrial membranes.	2003 Jun	12798477
Tocolysis: current controversies, future directions.	2004 Apr	15134284
Management options for preterm labour in Canada.	2004 Apr	15115623
Preterm birth.	2004 Jun	15652088
Centrally administered oxytocin elicits exaggerated grooming in oxytocin null mice.	2004 Jun	15219775
Delaying preterm delivery at the threshold of viability.	2004 Jun	15203596
Evaluation of the maternal and neonatal effects of the oxytocin antagonist, atosiban, in a cross-fostering study in rats.	2004 Nov	15336713
Visual compatibility of atosiban acetate with four drugs.	2005 Dec 1	16303899
Adverse effects of tocolytic therapy.	2005 Mar	15715600
Does insulin release kinins in rats?	2005 Nov 21	16297383
Synthesis of oxytocin analogues with replacement of sulfur by carbon gives potent antagonists with increased stability.	2005 Sep 30	16277299
Oxytocin stimulates secretory processes in lactating rabbit mammary epithelial cells.	2006 Jan 1	16166151

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 18:07:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:21 GMT 2025`
Record UNII	0P5DNO7CEF
Record Status	`FAILED`
Record Version

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Name

Type

Language

ATOSIBAN ACETATE [EMA EPAR]

Preferred Name

English

ATOSIBAN ACETATE

Common Name

English

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

Common 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, MONOACETATE (SALT)

Common 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)-DISULPHIDE, MONOACETATE (SALT)

Common 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)-DISULPHIDE, ACETATE (1:1)

Common Name

English

Atosiban acetate [WHO-DD]

Common 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, ACETATE (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98292