MEDRYSONE Chemical Properties

Melting point:

155-158°

alpha 

D +189° (in chloroform)

Boiling point:

492.3±45.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

14.53±0.70(Predicted)

color 

White to Off-White

Safety Information

WGK Germany 

3

RTECS 

TU5250000

MSDS

• Language:English Provider:SigmaAldrich

MEDRYSONE Usage And Synthesis

Description

6α-methyl-11β-hydroxy Progesterone is an anti-inflammatory steroid. It is a hydroxylated progesterone that lacks progestational and androgenic activity. It inhibits phytohemagglutinin-activated T cell proliferation in vitro with an IC₅₀ value of 2.9 μg/ml. 6α-methyl-11β-hydroxy Progesterone also inhibits TNF-α production in LPS-stimulated THP-1 cells (IC₅₀ = 30.54 μg/ml). Topical formulations containing 6α-methyl-11β-hydroxyprogesterone have been used to treat inflammatory ocular diseases.

Originator

HMS,Allergan,US,1970

Uses

glucocorticoid

Uses

Medrysone is a corticosteroid that is seen to increase intraocular pressure.

Definition

ChEBI: Medrysone is a corticosteroid hormone.

Manufacturing Process

Preparation of 11-Keto-6β-Methylprogesterone 3,20-bis-(Ethylene Ketal): A mixture of 5 g of 11-keto-6β-methylprogesterone [Spero et al, A Am. Chem. Soc., 78, 6213 (1956)], 503 ml of benzene, 26 ml of ethylene glycol, and 0.152 g of p-toluenesulfonic acid monohydrate was stirred and heated under reflux for 22 hours while water was removed by means of a water trap. The reaction mixture was then cooled to 30°C, 0.4 ml of pyridine was added, and stirring was continued for 10 minutes.
The reaction mixture was then shaken with 110 ml of water and the organic and aqueous layers separated. The organic layer was dried over sodium sulfate and evaporated under diminished pressure giving a residue. The thus obtained residue was recrystallized from methanol giving 2.68 g of 11-keto6β-methyl progesterone 3,20-bis-(ethylene ketal) having a MP of 168° to 175°C.
Preparation of 11β-Hydroxy-6α-Methylprogesterone: A mixture of 2.68 g of 11-keto-6β-methylprogesterone 3,20-bis-(ethylene ketal), 161 ml of tetrahydrofuran (previously distilled from lithium aluminum hydride), 1.34 g of lithium aluminum hydride and 14.5 ml of absolute ether was stirred and refluxed under nitrogen for 1.5 hours, then 27 ml of water was added cautiously, to decompose excess hydride. The resulting mixture was filtered and the filter cake was washed with 135 ml of ether. The combined filtrate and wash was shaken with 135 ml of water and separated. The aqueous layer was washed with four 55-ml portions of ether, then the organic layer and the washes were combined, washed once with water, and evaporated to dryness under diminished pressure leaving a tan residue.
The thus-obtained residue was dissolved in a mixture of 268 ml of methanol and 26.8 mi of 3 N aqueous sulfuric acid and heated under reflux for 40 minutes, with a color change from yellow to green. The reaction mixture was then cooled, neutralized by addition of 127 ml of 5% sodium bicarbonate solution, and concentrated under reduced pressure until almost all the methanol was removed. The resulting solid was removed by filtration, washed with water, dried, and twice crystallized from ethyl acetate to give 1.1 g of 11β-hydroxy-6α-methylprogesterone having a MP of 155° to 158°C, according to US Patent 2,864,837.

Therapeutic Function

Glucocorticoid

References

[1] the dictionary of drugs: chemical data: chemical data, structures and bibliographies[m]. springer, 2014.
[2] spaeth g l. hydroxymethylprogesterone: an anti-inflammatory steroid without apparent effect on intraocular pressure[j]. archives of ophthalmology, 1966, 75(6): 783-787.

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