A-Methapred

Base Information

• Chemical Name: A-Methapred
• CAS No.: 83-43-2
• Molecular Formula: C22H30O5
• Molecular Weight: 374.477
• Hs Code.: 2937290000
• ChEMBL ID: CHEMBL190259
• Mol file: 83-43-2.mol

Synonyms:6 alpha-Methylprednisolone Sodium Hemisuccinate;A-MethaPred;Hemisuccinate, Methylprednisolone;Methylprednisolone Hemisuccinate;Methylprednisolone Hemisuccinate Monosodium Salt;Methylprednisolone Sodium Hemisuccinate;Methylprednisolone Sodium Succinate;Methylprednisolone Succinate;Sodium Hemisuccinate, Methylprednisolone;Sodium Succinate, Methylprednisolone;Solu-Medrol;Solumedrol;Succinate, Methylprednisolone;Urbason-Soluble;UrbasonSoluble

Chemical Property of A-Methapred

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 1.86E-15mmHg at 25°C
• Melting Point: 228-237 °C (dec.)
• Refractive Index: 82 ° (C=1, Dioxane)
• Boiling Point: 571.8 °C at 760 mmHg
• PKA: 12.46±0.70(Predicted)
• Flash Point: 313.7 °C
• PSA: 94.83000
• Density: 1.28 g/cm³
• LogP: 1.80360
• Storage Temp.: 0-6°C
• Solubility.: chloroform/methanol (9:1): 50 mg/mL, clear, faintly yellow
• Water Solubility.: 0.12g/L(25 oC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 374.20932405
• Heavy Atom Count: 27
• Complexity: 754

Purity/Quality:

99% ^*data from raw suppliers

Methylprednisolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
• Uses: A glucocorticoid which displays anti-inflamatory and antioxidant properties and attenuates apoptosis in oligodendrocytes after injury. 6α-Methyl Prednisolone is neuroprotective. A glucocorticoid
• Therapeutic Function: Glucocorticoid
• Clinical Use: Adding a 6α-methyl group to prednisolone increases the glucocorticoid activity and effectively abolishes mineralocorticoid action. It has fivefold the glucocorticoid activity of hydrocortisone (prednisolone has fourfold the glucocorticoid activity) and none of its mineralocorticoid properties. It is used almost exclusively as a systemic product and is available as the free alcohol for oral administration and as various esters.
• Drug interactions: Metabolism in the liver occurs primarily via the CYP3A4 enzyme to inactive metabolites, which are excreted in the urine Aldesleukin: avoid concomitant use. Antibacterials: metabolism accelerated by rifampicin; metabolism inhibited by erythromycin and possibly clarithromycin; concentration of isoniazid possibly reduced. Anticoagulants: efficacy of coumarins and phenindione may be altered. Antiepileptics: metabolism accelerated by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone. Antifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism inhibited by ketoconazole and possibly itraconazole. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: rare reports of convulsions in patients on ciclosporin and high-dose corticosteroids; levels of ciclosporin increased with high dose methylprednisolone. Cobicistat: concentration possibly increased by cobicistat. Diuretics: enhanced hypokalaemic effects of acetazolamide, loop diuretics and thiazide diuretics. Vaccines: high dose corticosteroids can impair immune response to vaccines; avoid with live vaccines.

Technology Process of A-Methapred

There total 32 articles about A-Methapred which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6α-methylprednisolone-21-hydrogen succinate (2921-57-5) → Methylprednisolone (83-43-2) + 6α-methylprednisolone 17-hemisuccinate (77074-42-1)

Guidance literature:

With aq. buffer; In N,N-dimethyl-formamide; at 25 ℃; Rate constant; Mechanism; pH dependence;

DOI:10.1002/jps.2600730507

Reference yield:

17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (86401-94-7) → Methylprednisolone (83-43-2) + methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

With aq. buffer; In N,N-dimethyl-formamide; at 25 ℃; Rate constant; Mechanism; pH dependence;

DOI:10.1002/jps.2600730507

Reference yield:

6α-methylprednisolone 17-hemisuccinate (77074-42-1) → Methylprednisolone (83-43-2) + 6α-methylprednisolone-21-hydrogen succinate (2921-57-5)

Guidance literature:

With aq. buffer; In N,N-dimethyl-formamide; at 25 ℃; Rate constant; Mechanism; pH dependence;

DOI:10.1002/jps.2600730507

upstream raw materials:

methylprednisolone acetate

(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregna-1,4-dien-3-one

17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

6α-methylprednisolone-21-hydrogen succinate

Downstream raw materials:

11β,17α,20α,21-tetrahydroxy-6α-methylpregna-1,4-diene-3-one

11β,17α,20β,21-tetrahydroxy-6α-methylpregna-1,4-diene-3-one

11β,17α,21-trihydroxy-6α-methylpregna-4-ene-3,20-dione

6α-Methylprednisolone 17α,21-ethyl orthopropanoate

Refernces

• 1、 -. "A methylprednisolone production process and production apparatus (by machine translation)". Paragraph 0075; 0097-0099; 0100; 0108; 0109; 0120; 0121. . Retrieved 2019/01/07.
• 2、 -. "Mucosal adhesive device for long-acting delivery of pharmaceutical combinations in oral cavity". . . Retrieved 2008/06/13.