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Methylprednisolone

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Methylprednisolone Basic information
Methylprednisolone Chemical Properties
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Methylprednisolone Usage And Synthesis
  • Chemical PropertiesWhite to Off-White Crystalline Powder
  • OriginatorMedrol,Upjohn,US,1957
  • UsesA glucocorticoid
  • DefinitionChEBI: The 6alpha-stereoisomer of 6-methylprednisolone.
  • Manufacturing ProcessThe following process description is taken from US Patent 2,897,218. Six 100- ml portions of a medium in 250-ml Erlenmeyer flasks containing 1% glucose, 2% corn steep liquor (60% solids) and tap water was adjusted to a pH of 4.9. This medium was sterilized for 45 minutes at 15 psi pressure and inoculated with a one to two day growth of Septomyxa affinis ATCC 6737. The Erlenmeyer flasks were shaken at room temperature at about 24°C for a period of 3 days.
    At the end of this period, this 600-ml volume was used as an inoculum for ten liters of the same glucose-corn steep liquor medium which in addition contained 10 ml of an antifoam (a mixture of lard oil and octadecanol). The fermentor was placed into the water bath, adjusted to 28°C, and the contents stirred (300 rpm) and aerated (0.5 liter air/10 liters beer). After 17 hours of incubation, when a good growth developed and the acidity rose to pH 6.7, 2 g of 6α-methylhydrocortisone plus 1 g of 3-ketobisnor-4-cholen-22-al, dissolved in 115 ml of dimethylformamide, was added and the incubation (conversion) carried out at the same temperature and aeration for 24 hours (final pH 7.9).
    The mycelium (56 g dry weight) was filtered off and the steroidal material was extracted with methylene chloride, the methylene extracts evaporated to dryness, and the resulting residue chromatographed over a Florisil column. The column was packed with 200 g of Florisil and was developed with five 400-ml fractions each of methylene chloride, Skellysolve B-acetone mixtures of 9:1, 8:2, 7:3, 1:1, and methanol. The fraction eluted with Skellysolve Bacetone (7:3) weighed 1.545 g and on recrystallization from acetone gave, in three crops, 928 mg of product of MP 210° to 235°C. The sample prepared for analysis melted at 245° to 247°C.
  • brand nameMedrol (Pharmacia & Upjohn).
  • Therapeutic FunctionGlucocorticoid
  • General DescriptionMethylprednisolone, 11β,17,21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione, isavailable unmodified or as ester derivatives.
    Methylprednisolone acetate, USP
    Methylprednisolone sodium succinate, USP.
  • Mechanism of actionMethylprednisolone is an analog of prednisolone that exhibits a more prolonged effect than prednisolone and cortisone; it has practically no mineralocorticosteroid activity and is better tolerated.
  • Clinical UseAdding 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.
  • Safety ProfileModerately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Chemical SynthesisMethylprednisolone, 11β,17α,21-trihydroxy-6α-methylpregna-1, 4-dien-3,20-dione (27.1.38), differs from prednisolone in the presence of a methyl group at position C6 of the steroid skeleton of the molecule. This seemingly simple difference in structure requires a different approach to synthesis. It is synthesized from hydrocortisone (27.1.8), the carbonyl group of which initially undergoes ketalization by ethylene glycol in the presence of traces of acid, during which the double bond at position C4– C5 is shifted to position C5– C6, giving the diethyleneketal 27.1.34. The product is oxidized to an epoxide (27.1.35) using perbenzoic acid. Next, the resulting epoxide is reacted with methylmagnesium bromide, and subsequent removal of the ketal protection by hydrogen reduction gives the 5-hydroxy-6-methyl derivative of dihydrocortisone 27.1.36. The resulting β-hydroxyketone is dehydrated using an alkaline, and then the resulting 6α-methylcortisone (27.1.37) undergoes microbiological dehydration at position C1–C2, giving the desired methylprednisolone (27.1.38).

  • Veterinary Drugs and Treatments
  • Purification MethodsRecrystallise medrol from EtOAc. The UV has max at in 95% EtOH 243nm ( 14,875). The 21-acetoxy derivative has m 205-208o (from EtOAc), and [] D +95o ( c 1, CHCl3). [Spero et al. J Am Chem Soc 78 6213 1956; Fried et al. J Am Chem Soc 81 1235 1959; 1H NMR: Slomp & McGarvey J Am Chem Soc 81 2200 1959, Beilstein 8 IV 3498.]
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