Methylprednisolone Hemisuccinate CAS 2921-57-5

Methylprednisolone hemisuccinate, molecular formula C26H34O8, CAS 2921-57-5, white to slightly yellow powder, odorless, slightly bitter taste. It is easily soluble in water, ethanol and chloroform, but insoluble or insoluble in petroleum ether and ethyl acetate. Among them, the solubility in water is closely related to the pH value, and it is easy to decompose when the pH value is 3.0 to 7.0. It is chemically relatively stable, can be stored under common alkaline or acidic conditions, and can be heated repeatedly. However, the stability of the drug is also affected by factors such as light, oxygen, and humidity. The ionization constant (pKa) is 8.02. This means that below pH 8.02, the compound exists as a free acid, and above pH 8.02, the compound exists as an ion. It shows strong characteristic peaks in ultraviolet and infrared absorption spectra, which can be used for quantitative or qualitative analysis. In addition, techniques such as mass spectrometry and nuclear magnetic resonance can also be used to detect the structure and purity of the drug. is a synthetic glucocorticoid drug that contains a hemisuccinate group in its structure and is therefore a semiacidic compound.

Methylprednisolone hemisuccinate, also known as methylprednisolone succinate, is an artificially synthesized intermediate acting glucocorticoid drug with strong anti-inflammatory, anti allergic, anti shock, and immunosuppressive effects. Its chemical formula is C ₂₆ H ∝₄ O ₈, molecular weight is 474.54, and CAS number is 2921-57-5. The drug diffuses into cells and binds to glucocorticoid receptors, regulating gene expression and exerting a wide range of pharmacological effects.

Core therapeutic areas

 

1. Rheumatoid immune diseases
Methylprednisolone succinate is a first-line treatment for autoimmune diseases such as rheumatoid arthritis, systemic lupus erythematosus (SLE), and ankylosing spondylitis. It reduces joint swelling, pain, and morning stiffness symptoms by inhibiting the release of inflammatory factors such as IL-1 and TNF - α. For example, in the treatment of SLE, this drug can quickly control critical complications such as lupus nephritis and neuropsychiatric lupus, reducing the risk of organ damage.
2. Allergic diseases
It has salvage therapeutic value for severe allergic reactions such as anaphylactic shock and acute attacks of bronchial asthma. By stabilizing the mast cell membrane and inhibiting histamine release, symptoms such as dyspnea and laryngeal edema can be rapidly relieved. Clinical studies have shown that intravenous injection of methylprednisolone succinate can significantly improve lung function in patients with acute asthma attacks within 30 minutes.

 

3. Disease of respiratory system
Widely used in acute exacerbation of chronic obstructive pulmonary disease (COPD), idiopathic pulmonary fibrosis, etc. Its anti-inflammatory effect can reduce airway mucus secretion, inhibit alveolitis, and improve patient oxygenation index. For example, in the treatment of COPD, short-term use of this medication can reduce the need for mechanical ventilation and shorten hospitalization time.
4. Skin diseases
It has specific effects on autoimmune skin diseases such as pemphigus vulgaris and bullous pemphigoid. Promote blister healing by inhibiting the deposition of antibodies between epidermal cells. Research has shown that systematic application of methylprednisolone succinate can reduce the blister area of patients with pemphigus by more than 50% within one week.

Organ transplantation and adjuvant therapy for tumors

 

1. Organ transplant rejection reaction
As an immunosuppressant, this drug reduces the risk of acute rejection of transplanted organs by inhibiting T lymphocyte activation, decreasing cytokine secretion. After kidney transplantation, the use of combined calcineurin inhibitors (such as tacrolimus) can increase the one-year survival rate of transplanted kidneys to over 90%.
2. Neoadjuvant therapy
In hematological malignancies such as lymphoma and leukemia, methylprednisolone succinate can induce tumor cell apoptosis and alleviate side effects such as nausea and vomiting caused by chemotherapy. For example, in the induction therapy of acute lymphoblastic leukemia (ALL), this drug is a core component of the VP regimen (vincristine+prednisone).

Critical illness rescue and shock treatment

 

1. Septic shock
By enhancing the sensitivity of blood vessels to catecholamines, stabilizing cell membranes, and improving tissue perfusion. Clinical guidelines recommend that for patients with septic shock, if blood pressure still does not meet the standard after sufficient fluid resuscitation and use of vasoactive drugs, intravenous injection of methylprednisolone succinate (20mg/kg/time, once every 6 hours) can be administered.
2. Anaphylactic shock
As an adjuvant therapy with adrenaline, it can prevent delayed allergic reactions.

 

Research has shown that the combined use of adrenaline and methylprednisolone succinate can reduce the mortality rate of patients with anaphylactic shock from 15% to below 5%.

3. Neurogenic shock
In neurogenic shock caused by spinal cord injury, stroke, etc., this drug can reduce vascular dilation and inflammatory response, and stabilize hemodynamics. For example, in the treatment of acute spinal cord injury, early high-dose use (30mg/kg intravenous injection) can significantly improve neurological function prognosis.

Application in special clinical scenarios

 

1. Ophthalmic diseases
For ocular inflammatory diseases such as uveitis and optic neuritis, local or systemic use of methylprednisolone succinate can quickly control inflammation and prevent vision loss. Research has shown that intravitreal injection of this drug (4mg/0.1ml) can reduce the recurrence rate of inflammation in patients with uveitis by 60%.
2. Gastrointestinal diseases
During the acute phase of inflammatory bowel disease (such as Crohn's disease and ulcerative colitis), this drug can induce mucosal healing and reduce hormone dependence. For example, for patients with moderate to severe Crohn's disease, intravenous injection of methylprednisolone succinate (40-60mg/day) can achieve a clinical remission rate of 70% within 4 weeks.
3. Endocrine disorders
Used as a substitute therapy for adrenal cortex dysfunction and as an adjuvant therapy for thyroid crisis. It can inhibit the release of thyroid hormones, alleviate symptoms such as high fever and tachycardia.

Methylprednisolone hemisuccinate is a synthetic glucocorticoid drug, and its synthesis method generally includes the following steps:

1. Dehydration acylation reaction:

The reaction is to dehydrate and acylate the sugar compound with the representative structure of glycosyl-17-propionic acid and anhydrous acid catalyst (such as thionyl chloride) in solvents such as acetic anhydride or dichloromethane to obtain the corresponding Acylated products. For example, react 11β, 17α, 21-trihydroxypregna-1, 4-diene-3, 20-dione (glucocorticoid compounds) and C6H5COCl (phenylacetyl chloride) in anhydrous acetic anhydride to obtain 11β, 17α, 21-trihydroxypregna-1, 4-diene-3, 20-dione-21-phenylpropanoate.

2. Conversion to half esters:

The obtained acylated product was converted into a half ester in anhydrous methanol/potassium dihydrogen tetraacetate. For example, react 11β, 17α, 21-trihydroxypregna-1, 4-diene-3, 20-dione-21-phenylpropanoate with anhydrous methanol/potassium dihydrogen tetraacetate in acetic anhydride to generate 11β, 17α, 21- trihydroxypregna-1, 4-diene-3, 20-dione-21-phenylpropionate methanol hemisuccinate.

3. Hydrolysis:

The half-ester obtained in the previous step is reacted with a base (such as sodium hydroxide or sodium bicarbonate) under heating in ethanol containing water to obtain the final product. For example, dissolve 11β, 17α, 21-trihydroxypregna-1, 4-diene-3, 20-dione-21-phenylpropionate methanol hemisuccinate with NaOH (sodium hydroxide) in ethanol containing water at 45°C for 5 hours After that, get product.

It should be noted that it is very important to control the reaction conditions and reaction time in each step to ensure the purity and yield of the product. At the same time, safety measures also need to be taken into account during the synthesis of the drug to avoid harm to the body.

Methylprednisolone hemisuccinate is an artificially synthesized glucocorticoid drug. It has stable chemical properties and unique physical characteristics, which collectively determine its application value in the field of medicine. The following provides a detailed explanation from five aspects: chemical structure, physical properties, solubility, stability, and chemical activity.

The molecular formula of methyl prednisolone succinate is C26H34O8, with a molecular weight of 474.54. Its structure is formed by the connection of methyl prednisolone and succinic acid through an ester bond, and it belongs to a derivative of glucocorticoids. This structure endows it with both the core activities of anti-inflammatory and immunosuppression of glucocorticoids, and also improves the water solubility property through the succinate group.

This compound exhibits a white or off-white crystalline powder form at room temperature, with a fine and uniform texture. It has a relatively high melting point, typically above 230°C (as recorded in some literature as 234-236°C), indicating strong intermolecular forces and good thermal stability. The predicted density is 1.33 ± 0.1 g/cm³, and the refractive index is 1.593. These parameters reflect the tightness of its crystal structure and optical properties. During storage, it should be strictly controlled within a temperature range of 2-8°C and sealed in a dark environment to prevent degradation due to temperature fluctuations or exposure to light.

The solubility of methylprednisolone succinate exhibits significant selectivity:

Water solubility: Partially soluble in water, but the solubility increases with the increase of pH value. This is because the succinate groups can partially hydrolyze under alkaline conditions, releasing negatively charged carboxylate ions, thereby enhancing the interaction with water molecules.

Organic solvent solubility: Exhibits good solubility in organic solvents such as acetone and ethanol, which is particularly important in the formulation process. For example, when preparing an injection, acetone can be used as a solvent for dissolution, and then the organic solvent can be removed through freeze-drying to obtain a stable dry powder formulation.

This compound is extremely sensitive to storage conditions:

Temperature influence: High temperatures accelerate molecular movement, causing ester bonds to break or undergo oxidative degradation. Therefore, it needs to be stored at low temperatures to maintain stability.

Light influence: Ultraviolet rays may trigger photochemical reactions, damaging the molecular structure. Hence, it needs to be stored in a dark environment.

Shelf life: Under sealed conditions that meet storage requirements, its shelf life is typically 2 years. However, after opening, it should be used as soon as possible to avoid contamination and degradation.

After methyl prednisolone succinate diffuses into the cells, it specifically binds to the glucocorticoid receptor in the cytoplasm, forming a hormone-receptor complex. This complex enters the cell nucleus and can regulate the gene transcription process, inhibiting the synthesis of pro-inflammatory factors (such as interleukins, tumor necrosis factors, etc.), while promoting the expression of anti-inflammatory proteins (such as lipocalin proteins, anti-inflammatory cytokines, etc.). This mechanism makes it widely used in clinical treatment for various inflammatory and immune-related diseases such as rheumatic diseases, collagen diseases, allergic reactions, and organ transplant rejection reactions. Additionally, its water-soluble ester group design enables the drug to take effect quickly through intravenous injection or muscle injection, meeting the treatment needs for acute conditions.

1. What is Methylprednisolone Hemisuccinate?
It is a sugar-corticoid precursor drug for injection. It is modified with water-soluble succinate ester to enable it to be formulated as a water-soluble injection. Once in the body, it rapidly hydrolyzes into the active methylprednisolone, providing rapid efficacy. It is mainly used in acute critical conditions that require rapid and potent anti-inflammatory and immunosuppressive effects.
2. How is it different from methylprednisolone tablets?
The main difference lies in the administration route and the speed of onset. This product is administered by intravenous or intramuscular injection, which can quickly achieve a high blood drug concentration and is used for emergency treatment in hospitals (such as severe allergies, persistent asthma, and shock). The tablet (methylprednisolone) is taken orally and has a relatively slower onset, making it suitable for chronic treatment in outpatient settings.
3. What are the main purposes?
It is mainly used for emergency situations requiring intravenous administration, including but not limited to: severe allergic reactions, acute severe asthma attacks, septic shock (with adequate antibiotics), organ transplant rejection, and certain rheumatic immune crises (such as lupus crisis).
4. What special precautions should be taken when using it?
This is a prescription drug and should be used under the strict supervision of a doctor for a short period of time. Special attention should be paid to the risks it may pose, such as masking signs of infection, causing a sudden increase in blood sugar and blood pressure, triggering gastrointestinal bleeding, and causing mental abnormalities. Do not change the dosage or treatment plan on your own, and when stopping the medication, reduce the dosage gradually.

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