Sulprostone

EP3 and EP1 receptor agonist CAS# 60325-46-4

Sulprostone

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Chemical structure

Sulprostone

3D structure

Chemical Properties of Sulprostone

Cas No. 60325-46-4 SDF Download SDF
PubChem ID 5312153 Appearance Powder
Formula C23H31NO7S M.Wt 465.56
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in methyl acetate (supplied pre-dissolved - 5mg/ml)
Chemical Name (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
SMILES CS(=O)(=O)NC(=O)CCCC=CCC1C(C(CC1=O)O)C=CC(COC2=CC=CC=C2)O
Standard InChIKey UQZVCDCIMBLVNR-TWYODKAFSA-N
Standard InChI InChI=1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/b7-2-,14-13+/t17-,19-,20-,22-/m1/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.
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.
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.

Biological Activity of Sulprostone

DescriptionSelective EP3 and EP1 receptor agonist (Ki values are 0.6 and 21 nM respectively). Synthetic PGE2 analog and allodynic agent.

Sulprostone Dilution Calculator

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Sulprostone Molarity Calculator

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Preparing Stock Solutions of Sulprostone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.148 mL 10.7398 mL 21.4795 mL 42.959 mL 53.6988 mL
5 mM 0.4296 mL 2.148 mL 4.2959 mL 8.5918 mL 10.7398 mL
10 mM 0.2148 mL 1.074 mL 2.148 mL 4.2959 mL 5.3699 mL
50 mM 0.043 mL 0.2148 mL 0.4296 mL 0.8592 mL 1.074 mL
100 mM 0.0215 mL 0.1074 mL 0.2148 mL 0.4296 mL 0.537 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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References on Sulprostone

Sulprostone for postpartum hemorrhage in a parturient with a history of Tako-tsubo cardiomyopathy.[Pubmed:23830846]

J Clin Anesth. 2013 Jun;25(4):327-30.

A 32 year old parturient with a history of Tako-tsubo cardiomyopathy, who suffered from postpartum hemorrhage for which Sulprostone was administered without any adverse events, is reported. Anesthetic considerations related to the management of patient with a history of Tako-tsubo cardiomyopathy, especially triggers that may cause a recurrence, are described. The potential deleterious effects of Sulprostone in a patient with a history of Tako-tsubo cardiomyopathy are discussed.

The EP3 Agonist Sulprostone Enhances Platelet Adhesion But Not Thrombus Formation Under Flow Conditions.[Pubmed:26228833]

Pharmacology. 2015;96(3-4):137-43.

Platelets express the EP2, EP3 and EP4 receptors. Prostaglandin (PG) E2 has a biphasic effect on platelets. Low concentrations of PGE2 enhance platelet aggregation through the activation of the EP3 receptors, while at high concentrations it attenuates aggregation via the EP4 receptor. Consequently, EP3 receptor inhibition was shown to inhibit artherothrombosis, but had no influence on bleeding time in vivo. In this study, we investigated the role of the EP3 receptor in adhesion and thrombus formation under flow conditions in vitro. The EP3 agonist Sulprostone caused an increase in the adhesion of washed platelets to fibrinogen as well as to collagen under low shear stress, an effect that was blocked by the EP3 antagonist L-798106. In contrast, when whole blood was perfused over collagen-coated surfaces, Sulprostone did not enhance binding and thrombus formation of platelets on collagen; at high concentrations it even attenuated this response. We conclude that in more physiological models of thrombus formation, the role for EP3 receptors is limited, indirectly suggesting that the primary action of PGE2 in haemostasis might be an inhibitory one.

Consecutive intra-umbilical vein injection of misoprostol and intravenous sulprostone in the management of retained placenta.[Pubmed:23771186]

Arch Gynecol Obstet. 2014 Jan;289(1):35-40.

INTRODUCTION: Consecutive intra-umbilical vein injection of misoprostol and intravenous Sulprostone in the management of retained placenta (RP). PURPOSE: The general accepted treatment of RP is manual removal of the placenta (MRP), but medical intervention protocols were suggested. We evaluate a protocol of using intra-umbilical vein injection of misoprostol followed, if necessary, by intravenous Sulprostone. A reduction in the need for MRP and less blood loss was expected. METHODS: Cohort A (1 January 2007 to 31 September 2008), managed by an expectative protocol including active management of the third stage of labor and if necessary MRP performed 60 min after birth of the baby, was compared with cohort B (1 April 2009 to 31 December 2010) managed by medical intervention protocol. This protocol consisted of intra-umbilical vein injection of misoprostol and if not successful, 250 mug of Sulprostone was given intravenously in 30 min. All vaginal deliveries after 24 weeks of gestation, with RP after 20 min and blood loss <500 mL were included. An intention to treat analysis was performed, with the need for MRP as the primary outcome. RESULTS: Baseline characteristics were similar. In cohort A, 275 women met the inclusion criteria and 57 (20.7%) women needed MRP. In cohort B, 219 women were included and 35 (16%) women needed MRP. There was no significant difference in number of MRP, the amount of blood loss and other secondary outcomes. CONCLUSIONS: We conclude that the use of intra-umbilical vein injection of misoprostol and intravenous Sulprostone consecutively, does not reduce the number of MRPs as well as the total amount of blood loss in women with RP after 20 min. The study shows that changing obstetric management by extrapolating results from specific study groups to a general population may lead to other results.

Transient allodynia pain models in mice for early assessment of analgesic activity.[Pubmed:17700719]

Br J Pharmacol. 2008 Feb;153(4):769-74.

BACKGROUND AND PURPOSE: The most common preclinical models of neuropathic pain involve surgical ligation of sensory nerves, which is especially difficult in mice. Transient models of chemically sensitized allodynia are potentially useful for rapidly characterizing the analgesic profile of compounds and conducting mechanistic studies. EXPERIMENTAL APPROACH: Increasing doses of NMDA, Sulprostone (an EP1/EP3 prostaglandin receptor agonist) or phenylephrine (an alpha (1) adrenoceptor agonist) were injected intrathecally (i.t.) or i.p., and animals were subsequently assessed for allodynia. The effects of receptor antagonists and analgesic compounds on allodynia were also assessed. KEY RESULTS: A comparison of total body doses that cause allodynia following spinal or systemic administration indicated that NMDA induces allodynia in the spinal cord while Sulprostone and phenylephrine act through a peripheral mechanism. Inhibition of the allodynia with receptor antagonists indicated that each agent induces allodynia by a distinct mechanism. The three models were benchmarked using compounds known to be active in neuropathic pain patients and nerve injury animal models, including gabapentin, amitriptyline and clonidine. CONCLUSIONS AND IMPLICATIONS: These transient allodynia models are a useful addition to the toolbox of preclinical pain models. They are simple, rapid and reproducible, and will be especially useful for characterizing the pain phenotype of knockout mice.

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