SC-58125

Names

[ CAS No. ]:
162054-19-5

[ Name ]:
SC-58125

[Synonym ]:
5-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole
1H-Pyrazole, 5-(4-fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-
5-(4-Fluorophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole
5-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole

Biological Activity

[Description]:

SC-58125 is a potent and selective inhibitor of cyclooxygenase 2 (COX-2), with an IC50 of 0.04 μM. SC-58125 exhibits antitumor activity in vitro and in vivo, and it also can inhibit edema at the inflammatory site and is analgesic[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

hCOX-2:0.04 μM (IC50)

hCOX-1:>100 μM (IC50)

[In Vitro]

SC-58125 (0.001-100 μM) has a high degree of selectivity for the inducible form of COX-2 (IC50=1 μM) over the COX-1 (IC50>100 μM)[1]. SC-58125 (10 μM; 20-140 s) is time-dependent and is complete by 1 min, with a half-maximal inhibition at 20 s[1]. SC-58125 (25-100 μM; 3 d) inhibits the in vitro growth of HCA-7 and LLC cells[3]. SC-58125 (100 µM; 12 h) induces G2 arrest in LLC cells[3]. SC-58125 (25-100 μM; 3 d) decreases p34cdc2 levels in HCA-7 cells[3]. SC-58125 (100 µM; 24 or 72 h) does not induce apoptosis of HCA-7 and LLC cells[3]. Cell Proliferation Assay[3] Cell Line: HCA-7 and LLC cells Concentration: 0, 25, 50, 100 μM Incubation Time: 3 days Result: Reduced the cell number and MTT activity in both cell lines in a dose-dependent manner. Cell Cycle Analysis[3] Cell Line: LLC cells Concentration: 100 μM Incubation Time: 12 hours Result: Increased in the number of cells containing 4n DNA content in a dose- and time-dependent manner. Reduced the number of mitotic figures. Western Blot Analysis[3] Cell Line: HCA-7 cells Concentration: 0, 25, 50, 100 μM Incubation Time: 3 days Result: Resulted in a dose-dependent decrease in p34cdc2 activity with strong inhibition, even at the lowest concentration.

[In Vivo]

SC-58125 (10 mg/kg; i.p. every 48 h) inhibits the growth of established colorectal cancer xenografts in mice[3]. SC-58125 (10 mg/kg; a single i.p.) reduces tumor PGE2 levels in mice[3]. SC-58125 (10 mg/kg; a single i.p.) does not change the tumor levels of COX-1 and COX-2 protein in mice[3]. Animal Model: Athymic Sprague-Dawley mice are injected HCA-7 cells[3] Dosage: 10 mg/kg Administration: I.p. every 48 h; at the time of tumor implantation or 2 and 4 weeks later Result: Decreased the tumor growth rates significantly.

[References]

[1]. Gierse JK, et, al. A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 specific inhibitors. J Biol Chem. 1996 Jun 28; 271(26): 15810-4.

[2]. Seibert K, et, al. Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proc Natl Acad Sci U S A. 1994 Dec 6; 91(25): 12013-7.

[3]. Williams CS, et, al. A cyclooxygenase-2 inhibitor (SC-58125) blocks growth of established human colon cancer xenografts. Neoplasia. Sep-Oct 2001; 3(5): 428-36.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
512.6±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₁₂F₄N₂O₂S

[ Molecular Weight ]:
384.348

[ Flash Point ]:
263.8±30.1 °C

[ Exact Mass ]:
384.055573

[ PSA ]:
60.34000

[ LogP ]:
3.86

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.573

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
Xi

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ HS Code ]:
2933199090

Customs

[ HS Code ]: 2933199090

[ Summary ]:
2933199090. other compounds containing an unfused pyrazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

The dual role of prostaglandin E(2) in excitotoxicity and preconditioning-induced neuroprotection.

Eur. J. Pharmacol. 517(1-2) , 17-27, (2005)

Cyclooxygenase-2 is harmful in models of cerebral ischemia yet plays a protective role in preconditioning-induced ischemic tolerance in the heart. This study examined the mechanisms underlying cycloox...

CpG oligodeoxynucleotides induce cyclooxygenase-2 in human B lymphocytes: implications for adjuvant activity and antibody production.

Clin. Immunol. 125(2) , 138-48, (2007)

Synthetic CpG oligodeoxynucleotides (ODN), similar to DNA sequences found in certain microorganisms, have shown promise as adjuvants for humans by enhancing immune responses. Since antibodies are ofte...

Cyclooxygenase-2 activity contributes to neuronal expression of cyclin D1 after anoxia/ischemia in vitro and in vivo.

Brain Res. Mol. Brain Res. 132(1) , 31-7, (2004)

Cyclooxygenase-2 (COX-2) activity has been implicated in the pathogenesis of neuronal cell death in ischemia and other diseases, but the mechanism by which COX-2 exacerbates cell death is unknown. COX...