SC 51089Selective EP1 receptor antagonist CAS# 146033-02-5 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 146033-02-5 | SDF | Download SDF |
| PubChem ID | 132748 | Appearance | Powder |
| Formula | C22H20Cl2N4O3 | M.Wt | 459.33 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO | ||
| Chemical Name | 3-chloro-N'-(3-pyridin-4-ylpropanoyl)-6H-benzo[b][1,4]benzoxazepine-5-carbohydrazide;hydrochloride | ||
| SMILES | C1C2=CC=CC=C2OC3=C(N1C(=O)NNC(=O)CCC4=CC=NC=C4)C=C(C=C3)Cl.Cl | ||
| Standard InChIKey | ORMHJTXDPDGKIS-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C22H19ClN4O3.ClH/c23-17-6-7-20-18(13-17)27(14-16-3-1-2-4-19(16)30-20)22(29)26-25-21(28)8-5-15-9-11-24-12-10-15;/h1-4,6-7,9-13H,5,8,14H2,(H,25,28)(H,26,29);1H | ||
| 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 | Selective EP1 prostanoid receptor antagonist (Ki values are 1.3, 11.2, 17.5, 61.1, > 100, > 100, > 100, >100 and > 100 μM for EP1, TP, EP3, EP2, EP4, FP and DP receptors respectively). Attenuates PGE2-induced neuronal cell death in vitro and slows tumor growth in vivo. |
SC 51089 Dilution Calculator
SC 51089 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1771 mL | 10.8854 mL | 21.7708 mL | 43.5417 mL | 54.4271 mL |
| 5 mM | 0.4354 mL | 2.1771 mL | 4.3542 mL | 8.7083 mL | 10.8854 mL |
| 10 mM | 0.2177 mL | 1.0885 mL | 2.1771 mL | 4.3542 mL | 5.4427 mL |
| 50 mM | 0.0435 mL | 0.2177 mL | 0.4354 mL | 0.8708 mL | 1.0885 mL |
| 100 mM | 0.0218 mL | 0.1089 mL | 0.2177 mL | 0.4354 mL | 0.5443 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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Aminoacetyl moiety as a potential surrogate for diacylhydrazine group of SC-51089, a potent PGE2 antagonist, and its analogs.[Pubmed:8558534]
J Med Chem. 1996 Jan 19;39(2):609-13.
8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activity. During metabolism in cultured rat hepatocytes, SC-51089, which contains a diacylhydrazine moiety, has been shown to release hydrazine. Analogs of SC-51089, in which the diacylhydrazine functionality has been replaced by isosteric and isoelectronic groups, have been synthesized and have been shown to be analgesics and PGE2 antagonists of the EP1 subtype. This report discusses the structure-activity relationships within these series.
2,4-Disubstituted oxazoles and thiazoles as latent pharmacophores for diacylhydrazine of SC-51089, a potent PGE2 antagonist.[Pubmed:11197330]
Bioorg Med Chem. 2001 Jan;9(1):1-6.
8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activity. Analogues of SC-51089, in which the diacylhydrazine moiety has been replaced with 2,4-disubstituted-oxazoles and-thiazoles, are described.
Comparative metabolism of SC-42867 and SC-51089, two PGE2 antagonists, in rat and human hepatocyte cultures.[Pubmed:8165819]
Xenobiotica. 1994 Jan;24(1):25-36.
1. The metabolism of SC-42867 and SC-51089, two PGE2 antagonists, was studied in cultured rat and human hepatocytes. Both compounds possess an 8-chlorodibenzoxazepine moiety, but differ from each other by the nature of the side chain connected to the nitrogen atom. SC-42867 and SC-51089 and their in vitro metabolites were separated by reversed-phase hplc. The major metabolites of both compounds were identified by mass spectrometry (ms) analysis. 2. SC-42867 was metabolized on the tricyclic moiety only. Oxidative N-dealkylation with opening of the oxazepine ring was the major metabolic pathway obtained in rat hepatocytes. The metabolic profile obtained in cultured human hepatocytes was comparable with that of cultured rat hepatocytes. However, the compound was metabolized to a much lower extent by the human cells. 3. SC-51089 was extensively metabolized by both cultured rat and human hepatocytes. Human cells metabolized this compound quite differently than cultured rat hepatocytes. Aromatic hydroxylation with consequent glucuronidation and sulphation were the main metabolic pathways observed in cultured human hepatocytes. Oxidative N-dealkylation with opening of the oxazepine ring and consequent glucuronidation was the major metabolic pathway observed in rat hepatocytes. Further metabolism occurred, in contrast with the human hepatocytes, mainly on the side chain. 4. The present in vitro results are compared with data of previous in vivo studies performed in rat.
Effects of EP1 receptor on cerebral blood flow in the middle cerebral artery occlusion model of stroke in mice.[Pubmed:17600836]
J Neurosci Res. 2007 Aug 15;85(11):2433-40.
The lipid mediator prostaglandin E2 (PGE2) exhibits diverse biologic activity in a variety of tissues. Four PGE2 receptor subtypes (EP1-4) are involved in various physiologic and pathophysiologic conditions, but differ in tissue distribution, ligand-binding affinity, and coupling to intracellular signaling pathways. To characterize the role of the EP1 receptor, physiologic parameters (mean arterial blood pressure, pH, blood gases PaO2 and PaCO2, and body temperature), cerebral blood flow (CBF), and neuronal cell death were studied in a middle cerebral artery occlusion model of ischemic stroke in wild-type (WT) and EP1 knockout (EP1-/-) mice. The right middle cerebral artery was occluded for 60 min, and absolute CBF was measured by [14C] iodoantipyrine autoradiography. The effect of EP1 receptor on oxidative stress in neuronal cultures was investigated. Although no differences were observed in the physiologic parameters, CBF was significantly (P < 0.01) higher in EP1-/- mice than in WT mice, suggesting a role for this receptor in physiologic and pathophysiologic control of vascular tone. Similarly, neuronal cultures derived from EP1-/- mice were more resistant (90.6 +/- 5.8% viability) to tert-butyl hydroperoxide-induced oxidative stress than neurons from WT mice (39.6 +/- 17.2% viability). The EP1 receptor antagonist SC-51089 and calcium channel blocker verapamil each attenuated the neuronal cell death induced by PGE2. Thus, the prostanoid EP1 receptor plays a significant role in regulating CBF and neuronal cell death. These findings suggest that pharmacologic modulation of the EP1 receptor might be a means to improve CBF and neuronal survival during ischemic stroke.
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.[Pubmed:10634944]
Biochim Biophys Acta. 2000 Jan 17;1483(2):285-93.
Stable cell lines that individually express the eight known human prostanoid receptors (EP(1), EP(2), EP(3), EP(4), DP, FP, IP and TP) have been established using human embryonic kidney (HEK) 293(EBNA) cells. These recombinant cell lines have been employed in radioligand binding assays to determine the equilibrium inhibitor constants of known prostanoid receptor ligands at these eight receptors. This has allowed, for the first time, an assessment of the affinity and selectivity of several novel compounds at the individual human prostanoid receptors. This information should facilitate interpretation of pharmacological studies that employ these ligands as tools to study human tissues and cell lines and should, therefore, result in a greater understanding of prostanoid receptor biology.
