Medrysone

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Cat Number

API0232124

CAS Number

2668-66-8

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Product Detail Description Scientific Support Customer Q&A

CAS Number

2668-66-8

EINECS

220-208-7

Storage

Store at room temperature

Synonyms

Hydroxymesterone; U-8471; NSC-63278; 11beta-Hydroxy-6alpha-methylpregn-4-ene-3,20-dione; DTXSID6045371

Molecular Formula

C22H32O3

Molecular Weight

344.5

Smiles

C[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)CC4)C)O)C)C(=O)C

Appearance

White to off-white solid

Melting Point

155-158°C

Boiling Point

492.3±45.0°C (Predicted)

Relative Density

1.13±0.1 (Predicted)

General Description

Medrysone is a synthetic corticosteroid specifically formulated for ophthalmic use, possessing a unique chemical structure that distinguishes it from more potent glucocorticoids like dexamethasone. Its molecular configuration confers a favorable safety profile for ocular applications.

Mechanism of Action

The drug binds to the glucocorticoid receptor (NR3C1), modulating gene expression and leading to the induction of lipocortins. These inhibitory proteins block phospholipase A2, thereby suppressing the biosynthesis of prostaglandins and leukotrienes.

Application

Medrysone is indicated for the treatment of inflammatory and allergic conditions of the eye, including allergic conjunctivitis, vernal conjunctivitis, and episcleritis. It produces less elevation of intraocular pressure compared to dexamethasone or betamethasone, making it a preferred option for patients susceptible to steroid-induced ocular hypertension.

The anti‑inflammatory steroid medrysone (1) was biotransformed by Cunninghamella blakesleeana, Neurospora crassa, and Rhizopus stolonifer, yielding seven new metabolites (2–8) with hydroxylations at various positions. Single‑crystal X‑ray confirmed structures of four metabolites. Compound 7 (11β,16β‑dihydroxy) was the most potent inhibitor of T‑cell proliferation (IC₅₀ <0.2 μg/mL). Compounds 1 and 7 also inhibited TNF‑α production. All compounds were non‑toxic to 3T3, HeLa, and PC3 cells. Microbial transformation generated new hydroxylated derivatives with anti‑inflammatory potential.

Fig. 1 Biotransformation of medrysone (1) with Cunninghamella blakesleeana. (Bano S, et al., 2016)

References

Bano S, et al. New Anti-Inflammatory Metabolites by Microbial Transformation of Medrysone. PLoS One. 2016;11(4):e0153951.

Does Medrysone require protection from light and heat during storage?

Yes, it is photosensitive and thermolabile. Store in light-resistant containers at controlled room temperature (15-25°C), away from direct sunlight and heat sources.

Is Medrysone stable in ophthalmic suspension formulations?

Yes, when formulated with preservatives and protected from light, typically stable for 24 months under recommended storage.

What is the recommended storage humidity for Medrysone?

It is not significantly hygroscopic, but store in tightly sealed containers to prevent moisture absorption and potential microbial contamination in suspensions.

How is the impurity medrysone 21-aldehyde (oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits.