Rofecoxib

Description

Rofecoxib · CAS 162011-90-7 · C17H14O4S. UNII 0QTW8Z7MCR. LogP: 3.2.

Identification

CAS Registry Number	162011-90-7
PubChem CID	5090
Molecular formula	C17H14O4S
IUPAC name	3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one
UNII (FDA)	0QTW8Z7MCR

Computed Descriptors

Molecular Weight	314.4
XLogP3	2.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	314.06128010
Monoisotopic Mass	314.06128010
Topological Polar Surface Area	68.8
Heavy Atom Count	22
Formal Charge	0

Physical & Chemical Properties

LogP	3.2

Physical description & handling notes

• White to off-white to light yellow powder
• Insoluble
• Sparingly soluble in acetone, slightly soluble in methanol and isopropyl acetate, very slightly soluble in ethanol, practically insoluble in octanol, and insoluble in water.
• In water, 472 mg/L at 25 °C /Estimated/
• 3.2X10-9 mm Hg at 25 °C /Estimated/
• log Kow = 1.56 /Estimated/

GHS Hazard Classification

Reported hazard statements	H302 (100%)

Documented Uses

• Consumption (g per capita) in the USA (2002): 0.0493
• Condensation of phenylacetic acid with ethyl bromoacetate in the presence of triethylamine in THF yields ethyl 2-(phenylacetoxy)acetate, which is cyclized to the hydroxyfuranone using potassium tert-butoxide in tert-butanol. The reaction with trifluorosulfonyl anhydride and diisopropylethylamine in CH2Cl2 affords the corresponding trifluorosulfonate, which by reaction with LiBr in hot acetone yields the bromofuranone. The coupling with 4-(methylsulfanyl)phenylboronic acid with Na2CO3 and Pd[(C6H5)3P]4 as catalysts
• For the treatment of osteoarthritis, rheumatoid arthritis, acute pain in adults, and primary dysmenorrhea, as well as acute treatment of migraine attacks with or without auras.
• Rofecoxib is a nonsteroidal antiinflammatory drug (NSAID) that selectively inhibits cyclooxgenase-2 (Cox-2), which was used in the therapy of chronic arthritis and mild-to-moderate musculoskeletal pain. Rofecoxib was withdrawn in 2004 because of an association with an increase in cardiovascular events with its long term use. Rofecoxib had also been linked transient serum aminotransferase elevations during therapy and to rare instances of idiosyncratic drug induced liver disease.
• Nonsteroidal Antiinflammatory Drugs
• Rofecoxib (Class: Analgesics, Added Date: 05-2000)

Synonyms

rofecoxib; 162011-90-7; Vioxx; Ceoxx; 4-(4-(Methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; MK 966; MK-966; 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one; Vioxx Dolor; 4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone; MK-0966; MK0966; rofecoxibum; DTXSID2023567; TRM-201; 0QTW8Z7MCR

Frequently Asked Questions

What are the CAS number and molecular formula of Rofecoxib?

CAS 162011-90-7; molecular formula C17H14O4S; molecular weight — g/mol.

What other names is Rofecoxib known by?

rofecoxib, 162011-90-7, Vioxx, Ceoxx, 4-(4-(Methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one, MK 966.

Is Rofecoxib classified as hazardous?

Hazard statements reported: H302.

What are the key physical properties of Rofecoxib?

LogP: 3.2.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.