Rofecoxib (CAS 162011-90-7) — formula C17H14O4S, molecular weight 314.4.
Documented applications: Uses: Medication: anti-inflammatory, Use (kg) in USA (2002): 13900, Consumption (g per capita) in the USA (2002): 0.0493, Calculated removal (%): 22.3, Use Classification: Pharmaceuticals, Methods of Manufacturing: 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 in hot toluene gives 4-[4-(methylsulfanyl)phenyl]-3-phenylfuran-2(5H)-one, which is finally oxidized with 2KHSO5.KHSO4.K2SO4(oxone), Formulations, Preparations: Vioxx, Oral: Tablets: 12.5 mg Vioxx (Merck), 25 mg Vioxx (Merck), 50 mg Vioxx (Merck). Oral Suspension: 12.5 mg, 5 mL Vioxx (Merck), 25 mg, 5 mL Vioxx (Merck)., General Manufacturing Information:, Merck & Co., Inc. announced a voluntary withdrawal of Vioxx (rofecoxib) from the U.S. and worldwide market, due to safety concerns of an increased risk of cardiovascular events (including heart attack and stroke) in patients on Vioxx. Vioxx is a prescription COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) that was approved by FDA in May 1999 for the relief of the signs and symptoms of osteoarthritis, for the management of acute pain in adults, and for the treatment of menstrual symptoms, and was later approved for the relief of the signs and symptoms of rheumatoid arthritis in adults and children., Information available in 2004 indicated that Rofecoxib was used in the manufacture of pharmaceutical preparations in the following countries: Argentina, Australia, Austria, Belgium, Brazil, Canada, Chile, Colombia, Costa Rica, Croatia, Denmark, Ecuador, El Salvador, Finland, France, Germany, Greece, Guatemala, Honduras, Hong Kong, Hungary, India, Indonesia, Ireland, Israel, Italy, Malaysia, Mexico, Netherlands, New Zealand, Nicaragua, Norway, Panama, Poland, Portugal, Romania, Singapore, Slovenia, South Africa, Spain, Sweden, Switzerland, Thailand, Turkey, United Kingdom, USA, Yugoslavia (1, 2).
Rofecoxib is a chemical compound with CAS registry number 162011-90-7 and molecular formula C17H14O4S (molecular weight 314.4).
CAS number: 162011-90-7
Its molecular formula C17H14O4S comprises 17 C, 14 H, 4 O, 1 S atoms.
Also known as: Rofecoxib
The CAS registry number of Rofecoxib is 162011-90-7.
Molecular formula C17H14O4S, molecular weight 314.4.
It is also registered under: Rofecoxib.
Recorded applications: Uses: Medication: anti-inflammatory, Use (kg) in USA (2002): 13900, Consumption (g per capita) in the USA (2002): 0.0493, Calculated removal (%): 22.3, Use Classification: Pharmaceuticals, Methods of Manufacturing: 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 in hot toluene gives 4-[4-(methylsulfanyl)phenyl]-3-phenylfuran-2(5H)-one, which is finally oxidized with 2KHSO5.KHSO4.K2SO4(oxone), Formulations, Preparations: Vioxx, Oral: Tablets: 12.5 mg Vioxx (Merck), 25 mg Vioxx (Merck), 50 mg Vioxx (Merck). Oral Suspension: 12.5 mg, 5 mL Vioxx (Merck), 25 mg, 5 mL Vioxx (Merck)., General Manufacturing Information:, Merck & Co., Inc. announced a voluntary withdrawal of Vioxx (rofecoxib) from the U.S. and worldwide market, due to safety concerns of an increased risk of cardiovascular events (including heart attack and stroke) in patients on Vioxx. Vioxx is a prescription COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) that was approved by FDA in May 1999 for the relief of the signs and symptoms of osteoarthritis, for the management of acute pain in adults, and for the treatment of menstrual symptoms, and was later approved for the relief of the signs and symptoms of rheumatoid arthritis in adults and children., Information available in 2004 indicated that Rofecoxib was used in the manufacture of pharmaceutical preparations in the following countries: Argentina, Australia, Austria, Belgium, Brazil, Canada, Chile, Colombia, Costa Rica, Croatia, Denmark, Ecuador, El Salvador, Finland, France, Germany, Greece, Guatemala, Honduras, Hong Kong, Hungary, India, Indonesia, Ireland, Israel, Italy, Malaysia, Mexico, Netherlands, New Zealand, Nicaragua, Norway, Panama, Poland, Portugal, Romania, Singapore, Slovenia, South Africa, Spain, Sweden, Switzerland, Thailand, Turkey, United Kingdom, USA, Yugoslavia (1, 2).
Public-database records for Rofecoxib (CAS 162011-90-7), reproduced here for independent cross-checking.
| Reported hazard statements | H302 (100%) |
|---|
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
| LogP | 3.2 |
|---|
| CAS Registry Number | 162011-90-7 |
|---|---|
| PubChem CID | 5090 |
| 分子式 | C17H14O4S |
| IUPAC 名称 | 3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one |
| UNII（FDA） | 0QTW8Z7MCR |
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
| 分子量 | 314.4 |
|---|---|
| XLogP3 | 2.3 |
| 氢键供体数 | 0 |
| 氢键受体数 | 4 |
| 可旋转键数 | 3 |
| 精确质量 | 314.06128010 |
| 单同位素质量 | 314.06128010 |
| 拓扑极性表面积 | 68.8 |
| 重原子数 | 22 |
| 形式电荷 | 0 |
Rofecoxib · CAS 162011-90-7 · C17H14O4S. UNII 0QTW8Z7MCR. LogP: 3.2.
Source: PubChem / Wikidata; the batch COA governs where values differ.
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