Physicochemical Properties
| Molecular Formula | C24H29NAO5 |
| Molecular Weight | 420.473838567734 |
| Exact Mass | 420.191 |
| Elemental Analysis | C, 68.56; H, 6.95; Na, 5.47; O, 19.02 |
| CAS # | 496807-11-5 |
| Related CAS # | 88475-69-8 (sodium); 88430-50-6 (free acid); 496807-11-5 |
| PubChem CID | 23663404 |
| Appearance | Typically exists as White to light yellow solids at room temperature |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 30 |
| Complexity | 665 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)[O-])O)O.[Na+] |
| InChi Key | YTCZZXIRLARSET-WGMXHSAISA-M |
| InChi Code | InChI=1S/C24H30O5.Na/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28;/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28);/q;+1/p-1/b13-12+;/t15?,17-,19+,20+,21-,23-;/m1./s1 |
| Chemical Name | sodium;4-[(1S,2S,3aR,8bR)-2-hydroxy-1-[(E,3R)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoate |
| Synonyms | 496807-11-5; rel-Sodium 4-((1S,2S,3aR,8bR)-2-hydroxy-1-((3R,E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl)butanoate; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | IP; Prodrug of PGI2; Vasodilator |
| ln Vitro | The number of blood vessels created increased significantly after treatment with beraprost sodium (0.1, 1.0, and 10.0 μM; 24 hours), and BPS is crucial for angiogenic activity [1]. When endothelial cells were treated with beraprost sodium (0.1, 1.0, and 10.0 μM) for 24 hours, the amount of VE-cadherin in the cell-cell contact area increased, and their shape tended to be normal in contrast to cells grown in hypoxic environments [1]. |
| ln Vivo | Beraprost sodium is an oral medication that is administered once day for three to seven days at a dose of 0.6 mg/kg. It has the ability to lower renal oxidative stress and further prevent renal interstitial fibrosis. fibrosis [1]. |
| Enzyme Assay |
Tube formation assay[1] In brief, endothelial cells (1 × 104) were seeded in a 48-well plate coated with 100 μl of growth factor-reduced Matrigel TM and incubated with and without varied concentrations of BPS (Beraprost sodium) at 0.1, 1.0, and 10.0 μmol/l for tube stabilization for 24 h at 37 °C. Tube formation was quantified by measuring the total tube loops in five random microscopic fields with a computer-assisted microscope |
| Cell Assay | The HUVECs were cultured in a modified minimum essential medium supplemented with 10% fetal bovine serum and 1% mycillin at 37 °C in 5% CO2 and 95% air. HUVECs in hypoxia group were cultured for 12 h into an airtight humidified chamber flushed with a gas mixture containing 5% CO2, 95% N2, and 1% O2 at 37 °C. HUVECs in hypoxia + BPS group were cultured with BPS (Beraprost sodium) at 1.0 μmol/l. The cells were cultured according to the manufacturer’s instructions and the culture medium was changed every 2 or 3 days. HUVECs at passage 3 were used for the following experiments[1]. |
| Animal Protocol |
Animal/Disease Models: 6-8 weeks old C57Bl/6J male mice [1] Doses: 0.6 mg/kg Route of Administration: Oral; 0.6 mg/kg; one time/day; 3 or 7 days Experimental Results: Reduce renal interstitial fibrosis develop. |
| References |
[1]. Beraprost sodium mitigates renal interstitial fibrosis through repairing renal microvessels.J Mol Med (Berl). 2019 Jun;97(6):777-791. |
| Additional Infomation | Beraprost sodium is the organic sodium salt of beraprost. It is used in the treatment of chronic arterial occlusive disease and primary pulmonary hypertension in Japan. It has a role as an antihypertensive agent, a platelet aggregation inhibitor, a prostaglandin receptor agonist, a vasodilator agent and an anti-inflammatory agent. It contains a beraprost(1-). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~297.28 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.95 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.95 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (4.95 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3783 mL | 11.8915 mL | 23.7829 mL | |
| 5 mM | 0.4757 mL | 2.3783 mL | 4.7566 mL | |
| 10 mM | 0.2378 mL | 1.1891 mL | 2.3783 mL |