CAS Number162011-90-7
SynonymsRofecoxid; 4-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone; Rofecoxib; 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; 3-[phenyl-4-(4-methylsulphonyl)phenyl]-2-(5H)-furanone; MFCD00935806; Vioxx; Ceoxx; MK-0966; 4-[4-(Methylsulfonyl)phenyl]-3-phenyl; 4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; 2(5H)-Furanone,4-4-(methylsulfonyl)phenyl-3-phenyl; 4-(4-methylsulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one; Ceeoxx; 4-(4-methanesulfonylphenyl)-3-phenyl-5H-furan-2-one
Molecular FormulaC17H14O4S
Molecular Weight314.36
Purity≥98 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point577.6±50.0 °C at 760 mmHg
Melting Point207°C
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 162011-90-7 |
| Catalog No. | 2A-9012330 |
| Chinese Name | 罗非昔布 |
| Synonyms | Rofecoxid; 4-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone; Rofecoxib; 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; 3-[phenyl-4-(4-methylsulphonyl)phenyl]-2-(5H)-furanone; MFCD00935806; Vioxx; Ceoxx; MK-0966; 4-[4-(Methylsulfonyl)phenyl]-3-phenyl; 4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; 2(5H)-Furanone,4-4-(methylsulfonyl)phenyl-3-phenyl; 4-(4-methylsulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one; Ceeoxx; 4-(4-methanesulfonylphenyl)-3-phenyl-5H-furan-2-one |
| Molecular Formula | C17H14O4S |
| Molecular Weight | 314.36 |
| Purity | ≥98 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 577.6±50.0 °C at 760 mmHg |
| Melting Point | 207°C |
| Appearance | powder |
| Water Solubility | Water solubility: insoluble; water solubility: 472 |
| Storage Condition | Refrigerator |
| Application | Rofecoxib is a potent, orally available, specific inhibitor of COX-2, with IC50 values of 26 and 18 nM for human COX-2 in human osteosarcoma cells and Chinese hamster ovary cells, respectively; Rofeco |
| HTC | 29309070 |
| SMILES | [S](=O)(=O)(C)c1ccc(cc1)C2=C(C(=O)OC2)c3ccccc3 |
| InChI | 1S/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 |
| InChI Key | RZJQGNCSTQAWON-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/12330_1_162011_90_7.pdf |
| Bioactivity | Rofecoxib is a potent, specific and orally active COX-2 inhibitor, with IC50s of 26 and 18 nM for human COX-2 in human osteosarcoma cells and Chinese hamster ovary cells, with a 1000-fold selectivity for COX-2 over human COX-1 (IC50 > 50 μM in U937 cells and > 15 μM in Chinese hamster ovary cells). Related Catalog Signaling Pathways >> Immunology/Inflammation >> COX Research Areas >> Inflammation/Immunology Target Human COX-2:18 nM (IC50, in Chinese hamster ovary cells) Human COX-2:26 nM (IC50, in human osteosarcoma cells) In Vitro Rofecoxib (MK-0966) is a potent and orally active inhibitor of COX-2, with IC50s of 26 and 18 nM for human COX-2 in human osteosarcoma cells and Chinese hamster ovary cells, with a 1000-fold selectivity for COX-2 over COX-1 (IC50 >50 μM in U937 cells and >15 μM in Chinese hamster ovary cells). Rofecoxib time dependently inhibits purified human recombinant COX-2 (IC50=0.34 μM) but suppresses purified human COX-1 in a non-time-dependent manner that can only be observed at a very low substrate concentration (IC50=26 μM at 0.1 μM arachidonic acid concentration). Rofecoxib selectively inhibits lipopolysaccharide-induced, COX-2-derived PGE(2) synthesis with an IC50 value of 0.53 ± 0.02 μM compared with an IC50 value of 18.8 ± 0.9 μM for the inhibition of COX-1-derived thromboxane B(2) synthesis after blood coagulation[1]. Rofecoxib (36 μM) causes a cell proliferation of 68% in MPP89, of 58% in Ist-Mes-1 and 40% in Ist-Mes-2. MSTO-211H and NCI-H2452 treated with 36 μM of Rofecoxib have a survival of 97% and 90% respectively. Rofecoxib (36 μM) decreases COX-2 and mRNA levels in Ist-Mes-1, Ist-Mes-2 and MPP89 cell lines[3]. In Vivo Rofecoxib potently inhibits carrageenan-induced paw edema (ID50=1.5 mg/kg), carrageenan-induced paw hyperalgesia (ID50=1.0 mg/kg), lipopolysaccharide-induced pyresis (ID50=0.24 mg/kg), and adjuvant-induced arthritis (ID50=0.74 mg/kg/day) in rodent models. Rofecoxib also protects adjuvant-induced destruction of cartilage and bone structures in rats. In a 51Cr excretion assay for detection of gastrointestinal integrity in either rats or squirrel monkeys, rofecoxib shows no effect at doses up to 200 mg/kg/day for 5 days[1]. Rofecoxib (15 mg/kg, i.p.) reduces the blood vessels attached to the internal limiting membrane (ILM) in mice. COX-2 and VEGF protein expressions, COX-2 mRNA and VEGF mRNA are also significantly decreased by Rofecoxib in ROP mice[2]. Cell Assay The anti-proliferative activity of single drug treatments is assessed in a monolayer culture condition by plating Ist-Mes-1, Ist-Mes-2 and MPP89 cells in T25 flask. After 24 h, DMSO (at the same final concentration of that present in medium with drugs), 50 μM gefitinib or 36 μM Rofecoxib are added. The cells are then harvested at 48 h after treatment and analyzed by western blot and RT-PCR to evaluate the effect of the drugs on expression and mRNA levels of EGFR and COX-2. The expression of the cell cycle arrest genes and p-AKT, AKT, p-ERK and ERK is detected by Western blot to assess the antiproliferative activity of the two drugs in isolation (25 μM gefitinib or 4 μM Rofecoxib) and in combination 25 μM gefitinib+4 μM Rofecoxib[3]. Animal Admin Mice[2] Retinopathy of prematurity (ROP) is induced in C57BL/6J mice. The mice are randomly allocated into three experimental groups with 16 mice in each group: normal group-age-matched mice are maintained in room air from birth to P17 and are served as negative control; untreated ROP group-ROP is induced as described above without treatment and served as positive control; Rofecoxib-treated ROP group-ROP mice are treated daily with Rofecoxib (15 mg/kg body weight, intraperitoneally) from P12 to P17. Rofecoxib is dissolved in a 0.5% aqueous methylcellulose solution before administration[2]. References [1]. Rofecoxib, et al. Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther. 1999 Aug;290(2):551-60. [2]. Liu NN, et al. Rofecoxib inhibits retinal neovascularization via down regulation of cyclooxygenase-2 and vascular endothelial growth factor expression. Clin Exp Ophthalmol. 2015 Jul;43(5):458-65. [3]. Stoppoloni D, et al. Synergistic effect of gefitinib and rofecoxib in mesothelioma cells. Mol Cancer. 2010 Feb 2;9:27. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 577.6±50.0 °C at 760 mmHg Melting Point 207°C Molecular Formula C17H14O4S Molecular Weight 314.356 Flash Point 303.1±30.1 °C Exact Mass 314.061279 PSA 68.82000 LogP 1.34 Vapour Pressure 0.0±1.6 mmHg at 25°C Index of Refraction 1.619 InChIKey RZJQGNCSTQAWON-UHFFFAOYSA-N SMILES CS(=O)(=O)c1ccc(C2=C(c3ccccc3)C(=O)OC2)cc1 Storage condition Refrigerator |
| Use of | Properties Articles34 Name rofecoxib Synonym More Synonyms Rofecoxib Biological Activity Related Catalog Signaling Pathways >> Immunology/Inflammation >> COX Research Areas >> Inflammation/Immunology Human COX-2:18 nM (IC50, in Chinese hamster ovary cells) Human COX-2:26 nM (IC50, in human osteosarcoma cells) References [1]. Rofecoxib, et al. Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther. 1999 Aug;290(2):551-60. [2]. Liu NN, et al. Rofecoxib inhibits retinal neovascularization via down regulation of cyclooxygenase-2 and vascular endothelial growth factor expression. Clin Exp Ophthalmol. 2015 Jul;43(5):458-65. [3]. Stoppoloni D, et al. Synergistic effect of gefitinib and rofecoxib in mesothelioma cells. Mol Cancer. 2010 Feb 2;9:27. Chemical & Physical Properties Molecular Formula C17H14O4S Exact Mass 314.061279 PSA 68.82000 Index of Refraction 1.619 InChIKey RZJQGNCSTQAWON-UHFFFAOYSA-N Storage condition Refrigerator |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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