Physicochemical Properties
| Molecular Formula | C18H17FO2S |
| Molecular Weight | 316.38978 |
| Exact Mass | 316.093 |
| CAS # | 158959-32-1 |
| PubChem CID | 443373 |
| Appearance | White to off-white solid powder |
| LogP | 5.404 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 22 |
| Complexity | 516 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | GJGZQTGPOKPFES-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C18H17FO2S/c1-22(20,21)16-11-7-14(8-12-16)18-4-2-3-17(18)13-5-9-15(19)10-6-13/h5-12H,2-4H2,1H3 |
| Chemical Name | 1-fluoro-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene |
| 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
| Targets | In CHO cells transfected stably with human COX isoenzyme, SC57666 inhibits COX2 with an IC50 of 3.2±0.8 nM and a selectivity 1000 times greater than that of COX1 (IC50=6000±1900 nM) [2]. |
| ln Vitro |
In CHO cells transfected stably with human COX isoenzyme, SC57666 inhibits COX2 with an IC50 of 3.2±0.8 nM and a selectivity 1000 times greater than that of COX1 (IC50=6000±1900 nM) [2]. In CHO cells stably transfected with human COX isozymes, SC57666 inhibited arachidonic acid-dependent PGE₂ production with an IC₅₀ of 3.2 ± 0.8 nM for COX-2 and 6000 ± 1900 nM for COX-1, representing a selectivity ratio (COX-1/COX-2) of approximately 2000-fold. [2] In a human whole blood assay for COX-2 (LPS-induced PGE₂ production), the IC₅₀ value for SC57666 is not provided, but it is mentioned as one of the compounds for which more sensitive assays are required to discriminate their relative effects on COX-1. [2] In human platelets stimulated by calcium ionophore A23187, SC57666 inhibited COX-1 mediated TXB₂ production with an IC₅₀ of 2.1 ± 0.2 μM. [2] In a sensitive assay using U937 cell microsomes at a low arachidonic acid concentration (0.1 μM), SC57666 inhibited COX-1 activity with an IC₅₀ of approximately 3300 nM. [2] |
| ln Vivo | An adjuvant-induced arthritis model has demonstrated the oral activity of SC57666 (ED50=1.7 mpk). Intragastrically given SC57666 for 5 hours at 600 mpk, no gastric damage was seen in the mice. The administration of SC57666 orally to rats at 200 mpk for 72 hours did not result in any intestinal harm [1]. |
| References |
[1]. Selective cyclooxygenase inhibitors: novel 1,2-diarylcyclopentenes are potent and orally activeCOX2 inhibitors. J Med Chem. 1994 Nov 11;37(23):3878-81. [2]. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX2 inhibitor. Br J Pharmacol. 1997 May;121(1):105-17. |
| Additional Infomation |
SC-57666 is a stilbenoid. SC57666 (1-[2-(4-fluorophenyl)cyclopentene-1-yl]-4-(methylsulphonyl)benzene) is described as a selective cyclooxygenase-2 (COX-2) inhibitor and belongs to a series of novel 1,2-diarylcyclopentenes. It was used as a reference compound in this study comparing the biochemical and pharmacological profiles of various COX inhibitors. [2] The order of potency of various inhibitors in the U937 cell microsome COX-1 assay was: diclofenac > indomethacin ~ naproxen > nimesulide ~ meloxicam ~ piroxicam > NS-398 ~ SC57666 > SC-58125 > CGP 28238 ~ etodolac > L-745,337 > DFU. [2] |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~316.07 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.90 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 25.0 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: ≥ 2.5 mg/mL (7.90 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 25.0 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 | 3.1607 mL | 15.8033 mL | 31.6066 mL | |
| 5 mM | 0.6321 mL | 3.1607 mL | 6.3213 mL | |
| 10 mM | 0.3161 mL | 1.5803 mL | 3.1607 mL |