Physicochemical Properties
| Molecular Formula | C26H34O8 |
| Molecular Weight | 474.54336 |
| Exact Mass | 474.225 |
| CAS # | 2921-57-5 |
| Related CAS # | Methylprednisolone;83-43-2;Methylprednisolone succinate sodium;2375-03-3;Methylprednisolone succinate (Standard);2921-57-5 |
| PubChem CID | 16923 |
| Appearance | White to off-white solid |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 689.6±55.0 °C at 760 mmHg |
| Flash Point | 230.7±25.0 °C |
| Vapour Pressure | 0.0±4.9 mmHg at 25°C |
| Index of Refraction | 1.593 |
| LogP | 2.69 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 34 |
| Complexity | 981 |
| Defined Atom Stereocenter Count | 8 |
| SMILES | C[C@@]12[C@](C(COC(CCC(O)=O)=O)=O)(O)CC[C@@]1([H])[C@]3([H])C[C@H](C)C4=CC(C=C[C@]4(C)[C@@]3([H])[C@@H](O)C2)=O |
| InChi Key | IMBXEJJVJRTNOW-XYMSELFBSA-N |
| InChi Code | InChI=1S/C26H34O8/c1-14-10-16-17-7-9-26(33,20(29)13-34-22(32)5-4-21(30)31)25(17,3)12-19(28)23(16)24(2)8-6-15(27)11-18(14)24/h6,8,11,14,16-17,19,23,28,33H,4-5,7,9-10,12-13H2,1-3H3,(H,30,31)/t14-,16-,17-,19-,23+,24-,25-,26-/m0/s1 |
| Chemical Name | 4-[2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoic acid |
| Synonyms | Methylprednisolone hydrogen succinate |
| 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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | glucocorticoid receptor |
| ln Vitro | IL-10 is an endogenous antiinflammatory cytokine that inhibits TNF biosynthesis and protects mice from lipopolysaccharide (LPS)-induced lethality. As synthetic glucocorticoids are widely used as antiinflammatory agents, we analysed the effects of methylprednisolone administration on IL-10 biosynthesis during murine endotoxaemia. We found that low doses of methylprednisolone (2-10 mg/kg) markedly inhibited TNF production but did not affect serum levels of IL-10, while a high methylprednisolone dose (50 mg/kg) increased LPS-induced IL-10 levels. In parallel, we observed that LPS-induced IL-10 production is TNF-independent in this experimental setting. Experiments conducted in vitro indicated that methylprednisolone (from 0.01 to 100 micrograms/ml) also increased the biosynthesis of IL-10 by LPS-activated mouse peritoneal macrophages. We conclude that methylprednisolone differentially regulates IL-10 and TNF production induced by LPS both in vivo and in vitro at the macrophage level.[1] |
| ln Vivo | To investigate the influence of methylprednisolone therapy on the survival of retinal ganglion cells (RGCs), the neurons that form the axons of the ON, we used a rat model of myelin oligodendrocyte glycoprotein (MOG)-induced EAE. Optic neuritis was diagnosed by recording visual evoked potentials, and RGC function was monitored by measuring electroretinograms. Methylprednisolone treatment significantly increased RGC apoptosis during MOG-EAE. By Western blot analysis, we identified the underlying molecular mechanism: a suppression of mitogen-activated protein kinase (MAPK) phosphorylation, which is a key event in an endogenous neuroprotective pathway. The methylprednisolone-induced inhibition of MAPK phosphorylation was calcium dependent. Hence, we provide evidence for negative effects of steroid treatment on neuronal survival during chronic inflammatory autoimmune disease of the CNS, which should result in a reevaluation of the current therapy regimen.[2] |
| Enzyme Assay |
For Western blot analysis of B-cell lymphoma-2 (Bcl-2) levels, the primary antibody (sc-7382; Santa Cruz Biotechnology) was diluted 1:200 in 5% skim milk in PBS-T; for protein detection, an HRP-conjugated secondary antibody against mouse IgG was used (Santa Cruz Biotechnology; 1:2000 in 1% skim milk in PBS-T). p44-p42 MAPK protein levels were detected using a primary antibody (sc-93-G; Santa Cruz Biotechnology) diluted 1:500 in 1% skim milk in PBS-T, and an HRP-conjugated secondary antibody against goat IgG (Santa Cruz Biotechnology; 1:3000 in PBS-T). For Western blot analysis of phospho-p44-phospho-p42 MAPK levels, the primary antibody (Thr180/Tyr182; New England Biolabs) was diluted 1:200 in 1% skim milk in PBS-T; for protein detection, an HRP-conjugated secondary antibody against rabbit IgG was used (Santa Cruz Biotechnology; 1:3000 in PBS-T). Nitric oxide synthase (NOS)1 protein levels were detected using a primary antibody (sc-648; Santa Cruz Biotechnology), diluted 1:200 in 5% skim milk in PBS-T, and an HRP-conjugated secondary antibody against rabbit IgG (Santa Cruz Biotechnology; 1:2000 in 1% skim milk in PBS-T). |
| Animal Protocol | Animals were treated with intraperitoneal injections of methylprednisolone (20 mg/kg) or vehicle (0.9% NaCl) on days 1-3 or 4-6 of the disease. Other animal groups received intraperitoneal injections of mifepristone (RU 486) (10 mg/kg) alone, or together with methylprednisolone, or intravitreal injections of cobalt chloride (CoCl2) (2 μl of a 100 mm solution; Sigma) alone, or together with intraperitoneally given methylprednisolone on days 1-3 of the disease. To inhibit the activation of MAPKs, an additional animal group was treated with the intravitreally applied MAPK kinase (MEK) inhibitor 2′-amino-3′-methoxyflavone (PD 98059) (2 μl of a 20 mm solution.[2] |
| References |
[1] Clin Exp Immunol. 1996 Oct;106(1):91-6. [2] J Neurosci. 2003 Aug 6;23(18):6993-7000. |
| Additional Infomation |
Methylprednisolone succinate is a corticosteroid hormone and a hemisuccinate. A water-soluble ester of methylprednisolone used for cardiac, allergic, and hypoxic emergencies. A water-soluble ester of METHYLPREDNISOLONE used for cardiac, allergic, and hypoxic emergencies. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~210.73 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.27 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 25.0 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: ≥ 2.5 mg/mL (5.27 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 25.0 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: ≥ 2.5 mg/mL (5.27 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 25.0 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 | 2.1073 mL | 10.5365 mL | 21.0730 mL | |
| 5 mM | 0.4215 mL | 2.1073 mL | 4.2146 mL | |
| 10 mM | 0.2107 mL | 1.0537 mL | 2.1073 mL |