Rofecoxib

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Cat Number

API0232170

CAS Number

162011-90-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

162011-90-7

EINECS

803-260-0

Storage

Store at room temperature

Synonyms

Vioxx; Ceoxx; 4-(4-(Methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; MK 966

Molecular Formula

C17H14O4S

Molecular Weight

314.4

Smiles

CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3

Appearance

Off-white to pale yellow crystalline powder

Melting Point

207°C

Boiling Point

577.6±50.0°C at 760 mmHg (Predicted)

Relative Density

1.333±0.06 (Predicted)

General Description

Rofecoxib was a selective cyclooxygenase‑2 (COX‑2) inhibitor of the sulfonylphenyl furanone class, structurally distinct from the tricyclic selective COX‑2 inhibitors (e.g., celecoxib). Its chemical name is 4‑(4‑methylsulfonylphenyl)‑3‑phenylfuran‑2(5H)‑one. The methylsulfonyl group is critical for COX‑2 selectivity by occupying a unique side pocket in the enzyme.

Mechanism of Action

Rofecoxib selectively inhibits COX‑2 with a 50‑ to 100‑fold selectivity over COX‑1, blocking the conversion of arachidonic acid to prostaglandins involved in inflammation, pain, and fever. Unlike nonselective NSAIDs, it does not inhibit COX‑1‑derived prostaglandins that protect the gastric mucosa and regulate platelet aggregation. This selectivity reduces the risk of gastrointestinal ulceration and bleeding.

Application

Rofecoxib was indicated for the relief of signs and symptoms of osteoarthritis, rheumatoid arthritis, acute pain, and primary dysmenorrhea. It was also approved for familial adenomatous polyposis.

The hybrid drug KSS19 combines rofecoxib (COX‑2 inhibitor) with a cis‑stilbene from combretastatin A4 (CA4), preventing CA4 isomerization. KSS19 binds to COX‑2 and the colchicine site of tubulin. It potently inhibited proliferation of colon cancer cell lines (including CA4‑resistant HT29, 100‑fold more sensitive), blocked tubulin polymerization, induced G2/M arrest, suppressed COX‑2, inhibited migration/invasion, and showed anti‑angiogenic activity in HUVEC tube formation assays. In HT29 xenografts, KSS19 (25 mg/kg/day) significantly reduced tumor growth, downregulated COX‑2, Ki‑67, CD31, and upregulated cleaved caspase‑3. KSS19 is a rational hybrid drug for colorectal cancer.

Fig. 1 Molecular docking and affinity of KSS19 with tubulin and COX-2 proteins. (Punganuru SR, et al., 2018)

References

Punganuru SR, et al. Conception, synthesis, and characterization of a rofecoxib-combretastatin hybrid drug with potent cyclooxygenase-2 (COX-2) inhibiting and microtubule disrupting activities in colon cancer cell culture and xenograft models. Oncotarget. 2018;9(40):26109-26129.

Does Rofecoxib require protection from light during storage?

Yes, it is photosensitive. UV light can cause photodegradation and discoloration. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Rofecoxib?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate hydrolysis.

Is Rofecoxib stable under high-humidity conditions?

It is not hygroscopic and remains stable. However, store in tightly sealed containers to prevent potential moisture absorption.

How is the impurity rofecoxib sulfone (oxidation product) monitored?

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