MEDRYSONE

Absorption

Rapidly absorbed following oral administration.

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

The Uses of MEDRYSONE

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

The Uses of MEDRYSONE

glucocorticoid

Background

Medrysone is a corticosteroid used in ophthalmology.

Indications

For the treatment of allergic conjunctivitis, vernal conjunctivitis, episcleritis, and epinephrine sensitivity.

What are the applications of Application

6α-Methyl-11β-hydroxyprogesterone is a corticosteroid and anti-inflammatory

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

Pharmacokinetics

Medrysone is a topical anti-inflammatory corticoidsteroids for ophthalmic use. In patients with increased intraocular pressure and in those susceptible to a rise in intraocular pressure, there is less effect on pressure with medrysone than with dexamethasone or betamethasone. Corticoidsteroids inhibit the edema, fibrin deposition, capillary dilation, and phagocytic migration of the acute inflammatory response, as well as capillary proliferation, deposition of collagen, and scar formation.

Metabolism

Not Available

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.