Structure via PubChem · Public domain (PubChem)
rofecoxib
Sign in to saveAlso known as MK 966, 4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone, 3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one
Rofecoxib is a COX-2-selective nonsteroidal anti-inflammatory drug (NSAID). It was marketed by Merck & Co. to treat osteoarthritis, rheumatoid arthritis, juvenile rheumatoid arthritis, acute pain conditions, migraine, and dysmenorrhea. Rofecoxib was approved in the United States by the Food and Drug Administration (FDA) in May 1999, and was marketed under the brand names Vioxx, Ceoxx, and Ceeoxx. Rofecoxib was available by prescription in both tablets and as an oral suspension.
Key facts
- Drug.verifiedrevid
- 470623576
- Drug.IUPAC_name
- 4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one
- Drug.image
- Rofecoxib.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 170px
- Drug.image2
- Rofecoxib-3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Vioxx, Ceoxx, Ceeoxx, others
- Drug.pregnancy_AU
- C
- Drug.legal_status
- withdrawn worldwide
- Drug.routes_of_administration
- By mouth & i.m
- Drug.bioavailability
- 93%
- Drug.protein_bound
- 87%
- Drug.metabolism
- liver
- Drug.elimination_half life
- 17 hours
- Drug.excretion
- bile duct/kidney
- Drug.IUPHAR_ligand
- 2893
- Drug.CAS_number
- 162011-90-7
via Wikipedia infobox
Chemical data
- Formula
- C17H14O4S
- Molecular weight
- 314.4 g/mol
- IUPAC name
- 3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one
- SMILES
- CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
- InChIKey
- RZJQGNCSTQAWON-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 68.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,784 papers- Rofecoxib.Drugs · 1999
- Rofecoxib.Expert opinion on pharmacotherapy · 2000
- Rofecoxib for osteoarthritis.The Cochrane database of systematic reviews · 2005
- Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group.The New England journal of medicine · 2000
- Rofecoxib: an update on physicochemical, pharmaceutical, pharmacodynamic and pharmacokinetic aspects.The Journal of pharmacy and pharmacology · 2003
via PubMed
Wikidata facts
- Mass
- 314.061
Show 5 more facts
- chemical formula
- C₁₇H₁₄O₄S
- canonical SMILES
- CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
- World Health Organisation international non-proprietary name
- rofecoxib
- defined daily dose
- 25
- Commons category
- Rofecoxib
via Wikidata · CC0
~31 min read
Article
22 sectionsContents
- Mode of action
- Pharmacokinetics
- Efficacy
- Premenstrual acne
- Fabricated efficacy studies
- Side effects
- Heart and blood vessels
- VIGOR study and publishing controversy
- Alzheimer's disease
- APPROVe study
- Other studies
- Other COX-2 inhibitors
- Other NSAIDs
- Withdrawal
- Martin Report
- FDA position
- Litigation
- Possible return to market
- See also
- Footnotes
- References
- External links
Rofecoxib is a COX-2-selective nonsteroidal anti-inflammatory drug (NSAID). It was marketed by Merck & Co. to treat osteoarthritis, rheumatoid arthritis, juvenile rheumatoid arthritis, acute pain conditions, migraine, and dysmenorrhea. Rofecoxib was approved in the United States by the Food and Drug Administration (FDA) in May 1999, and was marketed under the brand names Vioxx, Ceoxx, and Ceeoxx. Rofecoxib was available by prescription in both tablets and as an oral suspension.
Rofecoxib gained widespread use among physicians treating patients with arthritis and other conditions causing chronic or acute pain. Worldwide, over 80 million people were prescribed rofecoxib at some time.