Retosiban
Based on 1 Customer Validation
Retosiban (GSK221149A) is a potent, selective, and orally active oxytocin receptor antagonist (Ki (hOT) = 0.65 nM, Ki (rOT) = 4.1 nM) with no detectable agonist activity. Retosiban has nanomolar affinity for the oxytocin receptor with >1400-fold selectivity over the closely related vasopressin receptors. Retosiban inhibits spontaneous and induces uterine contractions. Retosiban can be studied in research for preterm labour.
For research use only. We do not sell to patients.
- Purity: 98.95%
- CAS No.: 820957-38-8
- Formula: C27H34N4O5
- Molecular Weight:494.58
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Biological Activity
IC50: 0.65 nM (Oxytocin)[1]
Retosiban (Compound GSK221149A) (0.1-10 μM) produces parallel rightward shifts of oxytocin-induced concentration-response curves in rat isolated myometrial strips[4].
Retosiban (1 μM) alleviates the effect of stretch under high tension on myometrial contractility in tissues[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Retosiban (1 nM-1 μM, i.v., single dose) produces a dose-dependent decrease in oxytocin-induced uterine contractions with an ID50 = 0.27 mg/kg and IC50 = 180 nM in anaesthetized and non-pregnant Sprague-Dawley female rats[1].
Retosiban (Compound 74) (0.3-3 mg/kg, i.v., single dose) significantly reduced spontaneous uterine contractions in a dose-dependent manner in late-term pregnant rats[3].
Retosiban (Compound GSK221149A) (0.1-1 mg/kg, i.v., single dose) results in a dose-dependent reduction in oxytocin-induced uterine contractions in anesthetized rats[4].
Retosiban (5 mg/kg, p.o., once a day for 1 and 4 days) significantly blocks oxytoxin-induced uterine contractions by 72% in nulliparous female Sprague-Dawley rats[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Late-term pregnant rats[1]
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Dosage:0.3, 1, 3 mg/kg
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Administration:Intravenous injection (i.v.)
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Result:Decreased spontaneous contractions by 26, 33, and 44% respectively.
| NCT Number | Sponsor | Condition | Start Date |
Phase
|
|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS No. 820957-38-8
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Appearance Solid
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Molecular Weight 494.58
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Formula C27H34N4O5
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Color Off-white to yellow
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SMILES
O=C([C@@H](C1CC2=C(C=CC=C2)C1)N3)N([C@H](C4=COC(C)=N4)C(N5CCOCC5)=O)[C@H]([C@H](CC)C)C3=O
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Synonyms
GSK 221149; GSK 221149A
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 100 mg/mL (202.19 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (5.05 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (5.05 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (279 KB)
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SDS (254 KB)
- English - EN (254 KB)
- Français - FR (254 KB)
- Deutsch - DE (254 KB)
- Norwegian - NO (254 KB)
- Español - ES (254 KB)
- Swedish - SV (254 KB)
- Italian - IT (254 KB)
- Portuguese - PT (254 KB)
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Handling Instructions (2659 KB)
References
[1]. Liddle J, et al. The discovery of GSK221149A: a potent and selective oxytocin antagonist. Bioorg Med Chem Lett. 2008 Jan 1;18(1):90-4. [Content Brief]
[2]. Thornton, S., et al., (2015). Treatment of spontaneous preterm labour with retosiban: a phase 2 proof-of-concept study. British journal of clinical pharmacology, 80(4), 740-749. [Content Brief]
[3]. Borthwick, A. D., et al., (2011). The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor. Medicinal research reviews, 31(4), 576–604. [Content Brief]
[4]. McCafferty, G. P., et al., (2007). Use of a novel and highly selective oxytocin receptor antagonist to characterize uterine contractions in the rat. American journal of physiology. Regulatory, integrative and comparative physiology, 293(1), R299–R305. [Content Brief]
[5]. Moraitis, A. A., et al., (2015). The Effect of an Oxytocin Receptor Antagonist (Retosiban, GSK221149A) on the Response of Human Myometrial Explants to Prolonged Mechanical Stretch. Endocrinology, 156(10), 3511–3516. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.0219 mL | 10.1096 mL | 20.2192 mL | 50.5479 mL |
| 5 mM | 0.4044 mL | 2.0219 mL | 4.0438 mL | 10.1096 mL | |
| 10 mM | 0.2022 mL | 1.0110 mL | 2.0219 mL | 5.0548 mL | |
| 15 mM | 0.1348 mL | 0.6740 mL | 1.3479 mL | 3.3699 mL | |
| 20 mM | 0.1011 mL | 0.5055 mL | 1.0110 mL | 2.5274 mL | |
| 25 mM | 0.0809 mL | 0.4044 mL | 0.8088 mL | 2.0219 mL | |
| 30 mM | 0.0674 mL | 0.3370 mL | 0.6740 mL | 1.6849 mL | |
| 40 mM | 0.0505 mL | 0.2527 mL | 0.5055 mL | 1.2637 mL | |
| 50 mM | 0.0404 mL | 0.2022 mL | 0.4044 mL | 1.0110 mL | |
| 60 mM | 0.0337 mL | 0.1685 mL | 0.3370 mL | 0.8425 mL | |
| 80 mM | 0.0253 mL | 0.1264 mL | 0.2527 mL | 0.6318 mL | |
| 100 mM | 0.0202 mL | 0.1011 mL | 0.2022 mL | 0.5055 mL |
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