Oxyphenbutazone

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Cat Number

API0232174

CAS Number

129-20-4

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Product Detail Description Scientific Support Customer Q&A

CAS Number

129-20-4

EINECS

204-936-2

Storage

Store at room temperature

Synonyms

Tandearil; Flogitolo; Flogoril; Frabel; Crovaril; Oxazolidin; Visubutina; Oxifenylbutazon; Butapirone

Molecular Formula

C19H20N2O3

Molecular Weight

324.4

Smiles

CCCCC1C(=O)N(N(C1=O)C2=CC=C(C=C2)O)C3=CC=CC=C3

Appearance

White to off-white solid powder

Melting Point

96°C (monohydrate), 109-111°C (anhydrous)

Boiling Point

485.6°C at 760 mmHg

Relative Density

1.241

General Description

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID) belonging to the pyrazolidine class, and the active metabolite of phenylbutazone, containing a hydroxyl group at the para position of one phenyl ring. Its structure is a 1,2-diphenyl-3,5-pyrazolidinedione derivative. Oxyphenbutazone is a white to off-white crystalline powder with weak acidic properties.

Mechanism of Action

Oxyphenbutazone exerts its effects through non-selective, reversible inhibition of cyclooxygenase (COX-1 and COX-2), blocking prostaglandin and thromboxane synthesis. It also has uricosuric properties, inhibiting the reabsorption of uric acid in the proximal renal tubule, and stabilizes lysosomal membranes. The drug has a long half-life and extensive plasma protein binding.

Application

Oxyphenbutazone is indicated for the treatment of ankylosing spondylitis, rheumatoid arthritis, osteoarthritis, and acute gouty arthritis. Due to its significant toxicity profile, including aplastic anemia and agranulocytosis, its use is now severely restricted to specific conditions and is considered second-line therapy.

A fluorescence polarization-based high-throughput screening assay was developed for inhibitors of the EZH2-EED interaction. After optimizing tracer peptide sequences, fluorescein labeling positions, and assay conditions, the system achieved Z' factors >0.9, indicating robustness for HTS. Screening 1,600 FDA-approved drugs identified four potential inhibitors: apomorphine hydrochloride, oxyphenbutazone, nifedipine, and ergonovine maleate. This is the first reported HTS assay targeting this protein-protein interface, offering a tool for discovering novel EZH2-EED disruptors.

Fig. 1 Pilot screening of an in-house compound library. (Zhu MR, et al., 2018)

References

Zhu MR, et al. Development of a high-throughput fluorescence polarization assay for the discovery of EZH2-EED interaction inhibitors. Acta Pharmacol Sin. 2018;39(2):302-310.

Does Oxyphenbutazone require protection from light and moisture during storage?

Yes, it is sensitive to light and moisture. Light causes photodegradation and moisture promotes hydrolysis. Store in light-resistant, tightly sealed containers with desiccant.

What is the recommended storage temperature for Oxyphenbutazone?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which accelerate oxidation and discoloration.

Is Oxyphenbutazone stable in tablet and topical formulations?

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

How is the impurity 4-hydroxybutyric acid (a hydrolysis product) monitored?

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