(Deamino-Cys1,D-Tyr(Et)2,Thr4,Orn8)-Oxytocin acetate salt

Names

[ Name ]:
(Deamino-Cys1,D-Tyr(Et)2,Thr4,Orn8)-Oxytocin acetate salt

[Synonym ]:
1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin
MFCD00672436
antocin
ATOSIBAN ACETATE
oxytocin,1-(3-mercaptopropanoicacid)-2-(o-ethyl-d-tyrosine)-4-l-threonine-8-l
1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin
1-deamino-2d-tyr-(oet)-4-thr-8-orn-oxytocin
Tractocile
1-({(4R,7S,10S,13S,16R)-7-(2-Amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-(4-ethoxybenzyl)-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-L-prolyl-L-ornithylglycinamide
1-(3-Mercaptopropionic acid)-2-(3-(p-ethoxyphenyl)-D-alanine)-4-L-threonine-8-L-ornithineoxytocin
Atosiban
Glycinamide, 1-[[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-13-[(1S)-1-methylpropyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-yl]carbonyl]-L-prolyl-L-ornithyl-
[Mpr-D-Tyr(OEt)-Ile-Thr-Asn-Cys]-Pro-Orn-Gly-NH2
1-({(4R,7S,10S,13S,16R)-7-(2-Amino-2-oxoethyl)-13-[(2S)-2-butanyl]-16-(4-ethoxybenzyl)-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl}carbonyl)-L-prolyl-L-ornithylglycinamide

Biological Activity

[Description]:

Atosiban(RW22164; Tractocile) is a nonapeptide, desamino-oxytocin analogue, and a competitive vasopressin/oxytocin receptor antagonist (VOTra). Atosiban inhibits the oxytocin-mediated release of inositol trisphosphate from the myometrial cell membrane.IC50 value:Target: As a result, there is reduced release of intracellular, stored calcium from the sarcoplasmic reticulum of myometrial cells, and reduced influx of Ca2+ from the extracellular space through voltage gated channels. In addition, atosiban suppresses oxytocin-mediated release of PGE and PGF from the decidua.[1][2] In human pre-term labour, atosiban, at the recommended dosage, antagonises uterine contractions and induces uterine quiescence. The onset of uterus relaxation following atosiban is rapid, uterine contractions being significantly reduced within 10 minutes to achieve stable uterine quiescence.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Oxytocin Receptor

Research Areas >> Others

[References]

[1]. Sanu O, et al. Critical appraisal and clinical utility of atosiban in the management of preterm labor. Ther Clin Risk Manag. 2010 Apr 26;6:191-9.

[2]. Akerlund M, et al. The effect on the human uterus of two newly developed competitive inhibitors of oxytocin and vasopressin. Acta Obstet Gynecol Scand. 1985;64(6):499-504.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
1469.0±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₃H₆₇N₁₁O₁₂S₂

[ Molecular Weight ]:
994.189

[ Flash Point ]:
842.2±34.3 °C

[ Exact Mass ]:
993.441223

[ PSA ]:
416.27000

[ LogP ]:
-3.41

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.549

[ Storage condition ]:
−20°C

[ Water Solubility ]:
H2O: ≤100 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RS7590000

CHEMICAL NAME :: Oxytocin, 1-(3-mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornith ine

CAS REGISTRY NUMBER :: 90779-69-4

LAST UPDATED :: 198912

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C43-H67-N11-O12-S2

MOLECULAR WEIGHT :: 994.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 94 ug/kg

SEX/DURATION :: female 1-35 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

REFERENCE :: BJOGAS British Journal of Obstetrics and Gynaecology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.82- 1975- Volume(issue)/page/year: 94,1040,1987

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RS7590000

Articles

Reversal of peripheral nerve injury-induced hypersensitivity in the postpartum period: role of spinal oxytocin.

Anesthesiology 118(1) , 152-9, (2013)

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 preg...

Development and clinical experience with the new evidence-based tocolytic atosiban.

Acta Obstet. Gynecol. Scand. 81(7) , 633-41, (2002)

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 p...

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

Addict. Biol. 17(4) , 758-69, (2012)

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 (...