Physicochemical Properties
| Molecular Formula | C21H23NO3S |
| Molecular Weight | 369.479 |
| Exact Mass | 369.139 |
| CAS # | 395683-14-4 |
| PubChem CID | 11682175 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 604.1±55.0 °C at 760 mmHg |
| Flash Point | 319.1±31.5 °C |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.590 |
| LogP | 3.57 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 26 |
| Complexity | 645 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | AXMZZGKKZDJGAZ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C21H23NO3S/c1-4-13-22-14-19(16-9-11-18(12-10-16)26(3,24)25)20(21(22)23)17-7-5-15(2)6-8-17/h5-12H,4,13-14H2,1-3H3 |
| Chemical Name | 4-(4-methylphenyl)-3-(4-methylsulfonylphenyl)-1-propyl-2H-pyrrol-5-one |
| Synonyms | BAP909 BAP 909 BAP-909 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In U937 cells, imrecoxib (BAP-909) (0.1–10 µM; 24 hours) dose-dependently lowers COX-2 mRNA levels generated by PMA+LPS [1]. |
| ln Vivo | Irecoxib (BAP-909) (gastrointestinal administration; 5-20 mg/kg; 1 hour before carrageenan injection) can decrease carrageenan-induced acute inflammation, with the strongest inhibitory effect at 4 hours [1]. Imrecoxib (BAP-909) (GI; 5-20 mg/kg; starting on day 7; day 26) decreases secondary paw swelling and prevents heat-inactivated BCG-induced inflammatory polyarthritis [ 1]. |
| Cell Assay |
RT-PCR[1] Cell Types: U937 Cell Tested Concentrations: 0.1 µM; 1µM; 10 µM Incubation Duration: 24 hrs (hours) Experimental Results: diminished COX-2 mRNA levels. |
| Animal Protocol |
Animal/Disease Models: Rat carrageenan edema model [1] Doses: 5 mg/kg, 10 mg/kg, 20 mg/kg Administration route: gastrointestinal administration; 5-20 mg/kg; carrageenan injection Results in the first 1 hour: Different doses can inhibit the edema reaction. Animal/Disease Models: Rat adjuvant-induced arthritis (AIA) model [1] Doses: 5 mg/kg, 10 mg/kg, 20 mg/kg Route of Administration: gastrointestinal administration; 5-20 mg/kg; Starting on day 7; day 26 Experimental Results: 10 and 20 mg/kg doses inhibited adjuvant-induced chronic inflammation. |
| References |
[1]. Imrecoxib: a novel and selective cyclooxygenase 2 inhibitor with anti-inflammatory effect. Acta Pharmacol Sin. 2004 Jul;25(7):927-31. |
| Additional Infomation | Imrecoxib has been used in trials studying the treatment of Knee Osteoarthritis. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~270.65 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.63 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.63 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7065 mL | 13.5325 mL | 27.0651 mL | |
| 5 mM | 0.5413 mL | 2.7065 mL | 5.4130 mL | |
| 10 mM | 0.2707 mL | 1.3533 mL | 2.7065 mL |