4-[4-(Methylsulfonyl)phenyl]-3-phenyl-
Rofecoxib
CAS: 162011-90-7
Molecular Formula: C17H14O4S
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Names and Identifiers
| Name | Rofecoxib |
| Synonyms | VIOXX MK-0966 ROFECOXIB Rofecoxid Rofecoxib Rofecoxib(Vioxx) Rofecoxib (MK0966) 4-[4-(Methylsulfonyl)phenyl]-3-phenyl- 4-[4-(MethylSLdfonyl)phenyl]-3-phenyl-2(5H)-furanone 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one 4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone 4-[4-(Methylsulfonyl)-phenyl]-3-phenyl-2(5H)-furanone |
| CAS | 162011-90-7 |
| EINECS | 803-260-0 |
| InChI | InChI=1/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3 |
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Physico-chemical Properties
| Molecular Formula | C17H14O4S |
| Molar Mass | 314.36 |
| Density | 1.333±0.06 g/cm3(Predicted) |
| Melting Point | 207°C |
| Boling Point | 577.6±50.0 °C(Predicted) |
| Flash Point | 303.1°C |
| Water Solubility | 9mg/L(25 ºC) |
| Solubility | Soluble in water (<1 mg/ml at 25 °C), DMSO (63 mg/ml at 25 °C), methanol (slightly) |
| Vapor Presure | 2.42E-13mmHg at 25°C |
| Appearance | off-white (pale yellow) crystalline powder |
| Color | white to beige |
| Merck | 14,8248 |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Refractive Index | 1.619 |
| Use | A selective Cox-2 inhibitor. |
| In vitro study | Rofecoxib inhibits COX-2 dependent PGE2 production in human osteosarcoma cells with an IC50 of 26 nM. Rofecoxib is a purified time-dependent inhibitor of human recombinant COX-2 with an IC50 of 0.34 μm. Rofecoxib causes time-independent inhibition of purified human COX-1. Rofecoxib selectively inhibits lipopolysaccharide-induced, COX-derived PGE2 synthesis with an IC50 value of 0.53 μm in human whole blood assays, compared, inhibits the synthesis of COX-1 derived thromboxane B2 after blood coagulation with an IC50 value of 18.8 μm. Rofecoxib moderately inhibited phenacetin O-deethylation with an IC50 of 23 μm. Preincubation with microsomes and NADPH for 30 min significantly increased the inhibitory effect of Rofecoxib with an IC50 of 4.2 μm. The inactivation of CYP1A2 by Rofecoxib requires NADPH and is characterized by a K I of 4.8 μm. |
| In vivo study | Rofecoxib effectively inhibited carrageenan-induced paw swelling, carrageenan-induced paw hyperalgesia, and lipopolysaccharide-induced fever with IC50 of 1.5 mg/kg,1.0 mg/kg, and 0.24 mg/kg, respectively. Rofecoxib also blocked adjuvant-induced arthritis with an IC50 of 0.74 mg/kg/day. In rats, Rofecoxib also has a protective effect against adjuvant-induced damage to cartilage and bone structures. Oral administration of Rofecoxib reduces portal pressure in rats treated with CCl4 for 8 weeks. In addition, rofecoxib administration reduced the number of activated HSCs and downregulated the liver protein levels of three detectable types of collagen, laminin, VEGF and CTGF in ccl4-treated rats. |
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| WGK Germany | 3 |
| RTECS | LU5135000 |
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Reference
| Reference Show more | 1. Liu Zhaoqing, Wanzhong, Jiang Zheng, Tuo Xun. Study on the interaction between rofecoxib and bovine serum albumin [J]. Journal of Analytical Science, 2020,36(03):421-426. 2. [IF = 4.098] Linlin Xu et al."Probing the interaction between levamlodipine and hemoglobin based on spectroscopic and molecular docking methods." Spectrochim Acta A. 2019 Dec;223:117306 |
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Introduction
Rofecoxib is a COX-2 inhibitor with an IC50 of 18 nM.
Last Update：2022-10-16 17:14:14
4-[4-(Methylsulfonyl)phenyl]-3-phenyl- - Reference Information
| Indications | Rofecoxib is a non-steroidal anti-inflammatory drug and a selective inhibitor of cyclooxygenase-2. It is clinically used for osteoarthritis, acute pain and primary dysmenorrhea. |
| biological activity | Rofecoxib (MK-0966) is a COX-2 inhibitor with IC50 of 18 nM. |
| Target | Value |
| COX-2 | 18 nM |
| Use | Used to treat arthritis Type II cyclooxygenase (COX-2) inhibitor. Non-steroidal anti-inflammatory drugs, used to relieve symptoms of osteoarthritis. |
| production method | 197 g4-methylthio benzophenone is dissolved in 700ml of methanol and 350ml of dichloromethane, 881gMMPP is added within 30min, and stirred at room temperature for 3h. Filtered, the filtrate was washed with 2L saturated sodium bicarbonate aqueous solution and 1L saturated salt water. The aqueous solution is extracted with 2L dichloromethane, the extract and the organic layer are combined, dried and concentrated to obtain 240g of white solid 4-methylsulfonyl benzophenone. 174 g4-methylsulfonyl benzophenone is dissolved in 2.5L chloroform, 20mg aluminum trichloride is added at -5 ℃, and then 40ml bromine is added in 300ml chloroform. After the reaction, 1.5L of water was added, chloroform was removed, and the water layer was extracted with 1L of ethyl acetate. The extracts are combined, dried and concentrated. The crude product was recrystallized with 50/50 ethyl acetate/hexane to obtain 210g of white solid 2-bromo-1-(4-methylsulfonyl phenyl) ethanone. At 20 ℃,27.4g of phenylacetic acid and 60g of 2-bromo-1-(4-methylsulfonylphenyl) ethanone were dissolved in 630ml of acetonitrile, and then 30.8ml of triethylamine was slowly added. After stirring at room temperature for 20min, cool with an ice bath. Slowly add 60ml DBU and stir for 20min until the reaction is complete. Acidify with lmol/L hydrochloric acid (color changes from dark brown to yellow), then add 2.4L ice water mixture and stir a little. The precipitate was filtered out and washed with a small amount of water to obtain 64g of wet crude product. Dissolve it in 750rnl dichloromethane and add 300g silica gel. Concentrated until slightly dry, the residue is loaded into the top of the silica gel column and chromatography with 10% ethyl acetate/dichloromethane. After the expansion liquid was concentrated, 36.6g of product was obtained. 58% yield. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:54:55
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