Oxaprozin

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Cat Number

API0231536

CAS Number

21256-18-8

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Product Detail Description Scientific Support Customer Q&A

CAS Number

21256-18-8

EINECS

244-296-1

Storage

Store at room temperature

Synonyms

3-(4,5-Diphenyloxazol-2-yl)propanoic acid; Oxaprozine; Oxaprozinum; Deflam; Oxaprozina

Molecular Formula

C18H15NO3

Molecular Weight

293.3

Smiles

C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3

Appearance

White to off-white powder

Melting Point

154℃

Boiling Point

467℃

Relative Density

1.222

General Description

Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) belonging to the propionic acid class, structurally related to ibuprofen and naproxen. It is available in oral tablets and is distinguished by its long plasma half-life of approximately 50 hours, supporting once-daily dosing. The drug exhibits potent anti-inflammatory, analgesic, and antipyretic properties typical of this therapeutic class.

Mechanism of Action

Oxaprozin reversibly inhibits both cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes, thereby blocking the conversion of arachidonic acid to prostaglandins and thromboxane. This non-selective inhibition reduces the synthesis of pro-inflammatory mediators responsible for pain, swelling, and fever. Its long duration of action results from extensive plasma protein binding and slow elimination, providing sustained suppression of prostaglandin production throughout the dosing interval.

Application

It is indicated for the management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for mild to moderate pain relief. Once-daily administration offers a compliance advantage for patients requiring chronic NSAID therapy. As with all NSAIDs, it carries boxed warnings for increased risk of serious cardiovascular thrombotic events and gastrointestinal bleeding, limiting its use in certain high-risk populations.

In this open‑label, two‑period add‑on study in healthy males, co‑administration of the selective urate reabsorption inhibitor dotinurad with the NSAID oxaprozin reduced the urinary excretion rate of dotinurad glucuronide conjugates by 34.3% and increased the area under the plasma concentration‑time curve (AUC) by 16.5% compared with dotinurad alone. Peak plasma concentration remained essentially unchanged. Adverse events were few and similar between regimens. Despite the statistically significant changes in pharmacokinetic parameters, the authors conclude that no clinically meaningful drug‑drug interaction occurs, and the safety profile of dotinurad is not meaningfully altered by oxaprozin.

Fig. 1 Mean (± SD) cumulative urinary excretion rate versus end time point of urine collection interval for metabolites of dotinurad. (Furihata K, <i>et al</i>., 2020) Fig. 1 Mean (± SD) cumulative urinary excretion rate versus end time point of urine collection interval for metabolites of dotinurad. (Furihata K, et al., 2020)

References

Furihata K, et al. A drug-drug interaction study of a novel, selective urate reabsorption inhibitor dotinurad and the non-steroidal anti-inflammatory drug oxaprozin in healthy adult males. Clin Exp Nephrol. 2020; 24(Suppl 1):36-43.

Does Oxaprozin require protection from light during long-term storage?

Yes, it is photosensitive. Prolonged UV exposure can cause discoloration and degradation. Store in light-resistant containers, preferably amber glass or opaque HDPE.

What is the recommended storage temperature for Oxaprozin?

Store at controlled room temperature (15-25°C). It is thermally stable, but avoid temperatures above 30°C to prevent softening or melting of the crystalline powder.

Is Oxaprozin prone to hygroscopicity, and how is this managed?

It exhibits low hygroscopicity. However, in high-humidity environments (>70% RH), we recommend storing in tightly sealed containers with desiccant to prevent surface moisture absorption.

How is the impurity 3-(4-aminophenyl)propionic acid monitored during stability?

This process-related impurity is controlled using a validated HPLC method, ensuring it remains below pharmacopoeial limits throughout the product's shelf life.