Meprednisone

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Cat Number

API1247423

CAS Number

1247-42-3

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Product Detail Description Customer Q&A

CAS Number

1247-42-3

EINECS

214-996-1

Storage

Store at room temperature

Synonyms

Betapar; Meprednisona; Sch 4358; Meprednisonum; DTXSID8023260; NSC-527579

Molecular Formula

C22H28O5

Molecular Weight

372.5

Smiles

C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@H]3C(=O)C[C@@]2([C@]1(C(=O)CO)O)C)C

Appearance

White to off-white solid

Melting Point

204-206°C

Boiling Point

574.4±50.0°C (Predicted)

Relative Density

1.28±0.1 (Predicted)

General Description

Meprednisone is a synthetic glucocorticoid that is the 16β-methyl analogue of prednisone. The addition of a methyl group at the 16β position reduces mineralocorticoid activity and may alter pharmacokinetics. It is a prodrug that is converted in the liver to its active metabolite, meprednisolone (the 11β-hydroxy form). The molecule is structurally distinct from methylprednisolone, which has a 6α-methyl group.

Mechanism of Action

Meprednisone itself is inactive; it requires 11β-hydroxysteroid dehydrogenase type 1 reduction to meprednisolone, which then binds to cytoplasmic glucocorticoid receptors. The receptor-ligand complex modulates gene transcription, suppressing pro-inflammatory cytokines, inhibiting phospholipase A2, and reducing NF-κB activity. The 16β-methyl group reduces sodium-retaining activity compared to prednisone, resulting in less hypertension and edema at therapeutic doses.

Application

Meprednisone was indicated for inflammatory and autoimmune conditions such as rheumatoid arthritis, asthma, allergic disorders, and dermatologic diseases. It has a similar potency to prednisone but with slightly less mineralocorticoid effect. However, it is rarely used today, having been largely replaced by prednisone and methylprednisolone. The drug remains of historical interest as an example of 16β-substituted glucocorticoids.

Does Meprednisone require protection from light and moisture during storage?

Yes, it is sensitive to both light and moisture. Store in original, tightly sealed, light-resistant containers with desiccant to prevent hydrolysis and photodegradation.

What is the recommended storage temperature for Meprednisone?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidation and loss of the 16-methyl group.

Is Meprednisone stable in topical or oral formulations?

Yes, when formulated with standard excipients and protected from light.

How is the impurity prednisone (desmethyl meprednisone) monitored during stability?

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