Atosibanmixed antagonist of oxytocin and vasopressin receptors CAS# 90779-69-4 |
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Quality Control & MSDS
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| Cas No. | 90779-69-4 | SDF | Download SDF |
| PubChem ID | 68613 | Appearance | Powder |
| Formula | C43H67N11O12S2 | M.Wt | 994.19 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | RW22164; RWJ22164 | ||
| Solubility | H2O : 16.67 mg/mL (16.77 mM; Need ultrasonic) DMSO : ≥ 16.67 mg/mL (16.77 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide | ||
| SMILES | CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCCC3C(=O)NC(CCCN)C(=O)NCC(=O)N)CC(=O)N)C(C)O | ||
| Standard InChIKey | VWXRQYYUEIYXCZ-AVTFEHRISA-N | ||
| Standard InChI | 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent oxytocin receptor (OTR) antagonist. Inhibits oxytocin-induced increase in Ca2+ concentration in myometrial cells in vitro (IC50 = 5 nM) Activates NF-κB and MAPK pathways in human amnion via Gαi signaling, resulting in pro-inflammatory effects. Inhibits oxytocin-induced uterine contractions in vivo and in vitro. Effective in a rat preterm labor model. |
Atosiban Dilution Calculator
Atosiban Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.0058 mL | 5.0292 mL | 10.0584 mL | 20.1169 mL | 25.1461 mL |
| 5 mM | 0.2012 mL | 1.0058 mL | 2.0117 mL | 4.0234 mL | 5.0292 mL |
| 10 mM | 0.1006 mL | 0.5029 mL | 1.0058 mL | 2.0117 mL | 2.5146 mL |
| 50 mM | 0.0201 mL | 0.1006 mL | 0.2012 mL | 0.4023 mL | 0.5029 mL |
| 100 mM | 0.0101 mL | 0.0503 mL | 0.1006 mL | 0.2012 mL | 0.2515 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Atosibana is a mixed antagonist of oxytocin and vasopressin receptors [1].
Atosibana is a peptide and is a dual antagonist of oxytocin receptor (OTR) and vasopressin receptors (V1aR, V1bR, V2R). When acted as an OTR antagonist, atosibana showed pKi values of 7.9 and 7.2 for human OTR and rat OTR, respectively. Treatment of atosibana significantly inhibited cell growth in MDCK and HEK293 cells stably transfected with the human OTR with IC50 values of 15.4 nM and 20.8 nM, respectively. When acted as a vasopressin receptor antagonist, atosibana exerted pKi values of 9.8, 7.4 and 6.5 for hV1aR, hV1bR and hV2R, respectively. Atosibana has been shown to have efficacy in inhibiting uterine contractions and delaying preterm delivery. However, atosibana can not be used for long-term maintenance treatment since it is not orally bioavailable [1].
References:
[1] Borthwick A D. Oral oxytocin antagonists. Journal of medicinal chemistry, 2010, 53(18): 6525-6538.
[2] Reversi A, Rimoldi V, Marrocco T, et al. The oxytocin receptor antagonist atosiban inhibits cell growth via a “biased agonist” mechanism. Journal of Biological Chemistry, 2005, 280(16): 16311-16318.
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Evaluation of the efficacy of atosiban in pregnant women with threatened preterm labor associated with assisted reproductive technology.[Pubmed:27212183]
Eur Rev Med Pharmacol Sci. 2016 May;20(9):1881-7.
OBJECTIVE: The present study aimed to investigate the effectiveness of Atosiban in treating women with threatened preterm labor who had become pregnant through assisted reproductive technology (ART) and the corresponding pregnancy outcomes. PATIENTS AND METHODS: Seventy pregnant women with threatened preterm labor after ART were randomly divided into two groups, with 35 cases in the Atosiban group and 35 in the ritodrine group. The post-treatment effects and the corresponding pregnancy outcomes were observed. RESULTS: The efficacy of extending gestational age by 48 hours was significantly higher in the Atosiban group than in the ritodrine group (p<0.05), whereas the efficacy of extending gestational age by seven days was the same in the two groups (p>0.05). There was no significant difference between the Atosiban and ritodrine groups in the average gestational age at birth (p<0.05). The occurrence of side effects in the pregnant women was higher in the ritodrine group than in the Atosiban group (p<0.05), although the prevalence of abnormal fetal heart rate was not significantly different (p>0.05). Both the perinatal mortality rate and the prevalence of neonatal asphyxia were significantly lower in the Atosiban group than in the ritodrine group (p<0.05). When the medication was applied at a gestational age of fewer than 28 weeks, the perinatal mortality rate and the prevalence of neonatal pneumonia were significantly lower in the Atosiban group compared with the ritodrine group (p<0.05). When the first drug administration was at a gestational age of 28 weeks or later, the need for neonatal pediatric treatment was significantly reduced in the Atosiban group relative to the ritodrine group. Independent of when the drug administration was initiated, there were no significant differences between the Atosiban and ritodrine groups in the occurrences of neonatal asphyxia, acute respiratory distress syndrome (ARDS), neonatal brain injury, or neonatal sepsis (p>0.05). CONCLUSIONS: Administration of Atosiban has a comparatively better effect than that of ritodrine on pregnant women who underwent ART and is safe and effective at preventing immediate preterm birth. Atosiban is significantly better than ritodrine at reducing the rates of perinatal mortality and neonatal pneumonia, and the perinatal outcomes for those who began to use Atosiban at a gestational age of fewer than 28 weeks were even better.
Differential Effects of Oxytocin Receptor Antagonists, Atosiban and Nolasiban, on Oxytocin Receptor-Mediated Signaling in Human Amnion and Myometrium.[Pubmed:28188254]
Mol Pharmacol. 2017 Apr;91(4):403-415.
One of the most established roles of oxytocin (OT) is in inducing uterine contractions and labor. Apart from inducing contractions, our recent studies showed that OT can also activate proinflammatory pathways in both human myometrial and amnion cells, which suggests that the proinflammatory role of OT should be taken into account when developing tocolytics targeting the OT/oxytocin receptor (OTR) system. The OTR antagonist, Atosiban, is currently used therapeutically for the treatment of preterm labor. We previously showed that Atosiban fails to inhibit the proinflammatory effects of OT in human amnion; Atosiban alone activates nuclear factor-kappaB (NF-kappaB) and mitogen activated protein kinases, thus upregulating downstream prolabor genes. In contrast with our findings with Atosiban, the presence of the orally active OTR antagonist, nolasiban, reduced the effect of OT on NF-kappaB and p38 kinase activation in both myometrial and amnion cells. Consistent with the activation of these inflammatory mediators, OT led to increases in the expression of cyclooxygenase-2 and phosphorylated cytosolic phospholipase A2, which was reflected in prostaglandin E2 synthesis. Inhibition of NF-kappaB activation by nolasiban also translated to suppression of downstream prolabor gene expression, such as cyclooxygenase-2, C-C motif chemokine ligand 2, interleukin-6, and interleukin-8. We also demonstrated that nolasiban treatment alone has no significant stimulatory effect on both the myometrium and amnion. In conclusion, our findings indicate that nolasiban possesses promising potential as a novel tocolytic agent for both acute and maintenance therapy, as it inhibits both myometrial contractions and the proinflammatory effects of OT without the biased agonist effects.
Atosiban versus fenoterol as a uterine relaxant for external cephalic version: randomised controlled trial.[Pubmed:28126898]
BMJ. 2017 Jan 26;356:i6773.
OBJECTIVE: To compare the effectiveness of the oxytocin receptor antagonist Atosiban with the beta mimetic fenoterol as uterine relaxants in women undergoing external cephalic version (ECV) for breech presentation. DESIGN: Multicentre, open label, randomised controlled trial. SETTING: Eight hospitals in the Netherlands, August 2009 to May 2014. PARTICIPANTS: 830 women with a singleton fetus in breech presentation and a gestational age of more than 34 weeks were randomly allocated in a 1:1 ratio to either 6.75 mg Atosiban (n=416) or 40 mug fenoterol (n=414) intravenously for uterine relaxation before ECV. MAIN OUTCOME MEASURES: The primary outcome measures were a fetus in cephalic position 30 minutes after the procedure and cephalic presentation at delivery. Secondary outcome measures were mode of delivery, incidence of fetal and maternal complications, and drug related adverse events. All analyses were done on an intention-to-treat basis. RESULTS: Cephalic position 30 minutes after ECV occurred significantly less in the Atosiban group than in the fenoterol group (34% v 40%, relative risk 0.73, 95% confidence interval 0.55 to 0.93). Presentation at birth was cephalic in 35% (n=139) of the Atosiban group and 40% (n=166) of the fenoterol group (0.86, 0.72 to 1.03), and caesarean delivery was performed in 60% (n=240) of women in the Atosiban group and 55% (n=218) in the fenoterol group (1.09, 0.96 to 1.20). No significant differences were found in neonatal outcomes or drug related adverse events. CONCLUSIONS: In women undergoing ECV for breech presentation, uterine relaxation with fenoterol increases the rate of cephalic presentation 30 minutes after the procedure. No statistically significant difference was found for cephalic presentation at delivery. TRIAL REGISTRATION: Dutch Trial Register, NTR 1877.
Application of atosiban in frozen-thawed cycle patients with different times of embryo transfers.[Pubmed:27147474]
Gynecol Endocrinol. 2016 Oct;32(10):811-815.
This prospective cohort study aimed to examine the effects of Atosiban, given before transfer of frozen-thawed embryo to women with different number of embryo transfer (ET) cycles. Atosiban treatment significantly increased implantation rate and clinical pregnancy rate in the third and more than three ET groups. However, there were no significant increases in the above parameters in the first and second ET groups. Our study showed that patients those who underwent the third or more than three ET cycles were inclined to higher uterine contractions and serum oxytocin level, thus Atosiban treatment starting from the third ET cycle may be effective in improving embryo implantation. This is the first study to evaluate the optimal Atosiban treatment window corresponding to the number of ET cycles of the patients.
