Flosulide

Names

[ Name ]:
Flosulide

[Synonym ]:
n-[6-(2,4-difluorophenoxy)-1-oxo-2,3-dihydro-1h-inden-5-yl]methanesulfonamide
N-[6-(2,4-difluorophenoxy)-2,3-dihydro-1-oxo-1H-inden-5-yl]methanesulfonamide
6-(2,4-difluorophenoxy)-5-methylsulfonylamino-1-indanone
5-methanesulfonamido-6-((2,4-difluorophenyl)oxy)-1-indanone
Flosulida [INN-Spanish]
Flosulidum
N-[6-(2,4-Difluoro-phenoxy)-1-oxo-indan-5-yl]-methanesulfonamide
Flosulidum [INN-Latin]
N-(6-(2,4-Difluorophenoxy)-1-oxo-5-indanyl)methanesulfonamide
Flosulide
Flosulida

Biological Activity

[Description]:

Flosulide is a potent and selective COX-2 inhibitor, used for the treatment for inflammatory diseases.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

COX-2

[In Vitro]

Flosulide (1 nM-100 μM) causes a concentration-dependent and finally complete inhibition of PGE2 production in the OSC-2 cell line, but with no effect on PG formation in the OSC-1 cells. Flosulide completely suppresses mitotic activity of OSC-2 cells, whereas mitotic activity of OSC-1 cells remain unchanged[2].

[In Vivo]

In normovolemic rats, flosulide increases renal plasma flow (RPF) and and glomerular filtration rate (GFR). In hypovolemic rats, flosulide (5-25 mg/kg) reduces RPF and GFR. Flosulide at 5 mg/kg reduces 6-keto-PGF1alpha whereas at 25 mg/kg and after indomethacin at 10 mg/kg a fall in 6-keto-PGF1alpha and TXB2 appeares[1]. Flosulide (0.75 mg/day) significantly reduces proteinuria as compared to aspirin treatment. Plasma protein and albumin levels are significantly lower in the aspirin-treated group than in flosulide-treated rats[3].

[Cell Assay]

The proliferation of the esophageal tumor cell lines is determined using the cell proliferation kit II. Tumor cells are incubated with flosulide and NS-398 at different concentrations for 48 h in DMEM containing FCS (10%), penicillin (100 units/mL), and streptomycin (0.1 mg/mL). After this time, the XTT labeling mixture is added, followed by 4 h of incubation and measurement of absorbance at 490 nm.

[References]

[1]. Turull A, et al. Acute effects of the anti-inflammatory cyclooxygenase-2 selective inhibitor, flosulide, on renal plasma flow and glomerular filtration rate in rats. Inflammation. 2001 Apr;25(2):119-28.

[2]. Zimmermann KC, et al. Cyclooxygenase-2 expression in human esophageal carcinoma. Cancer Res. 1999 Jan 1;59(1):198-204.

[3]. Heise G, et al. Different actions of the cyclooxygenase 2 selective inhibitor flosulide in rats with passive Heymann nephritis. Nephron. 1998 Oct;80(2):220-6.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.506g/cm3

[ Boiling Point ]:
446.9ºC at 760 mmHg

[ Molecular Formula ]:
C₁₆H₁₃F₂NO₄S

[ Molecular Weight ]:
353.34100

[ Flash Point ]:
224.1ºC

[ Exact Mass ]:
353.05300

[ PSA ]:
80.85000

[ LogP ]:
4.41130

[ Index of Refraction ]:
1.62

[ Storage condition ]:
2-8℃

Synthetic Route

Click to get detail synthetic route

Related Compounds

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