3916. Exisulind

Nomenclature

CAS number: 59973-80-7
(1Z)-5-Fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-1H-indene-3-acetic acid; cis-5-fluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-3-acetic acid; sulindac sulfone; FGN-1; Aptosyn (Cell Pathways).
C20H17FO4S; mol wt 372.41.
C 64.50%, H 4.60%, F 5.10%, O 17.18%, S 8.61%.

Description and references

Sulfone metabolite of sulindac, q.v.; induces apoptosis of cancer cells. Identification as metabolite: H. B. Hucker et al., Drug Metab. Dispos. 1, 721 (1973). Prepn: H. Jones et al., J. Carbohydr. Nucleosides Nucleotides 3, 369 (1974). Antiproliferative effect vs colon cancer cells: L. J. Hixson et al., Cancer Epidemiol. Biomarkers Prev. 3, 433 (1994). HPLC determn in serum: M. Siluveru, J. T. Stewart, J. Chromatogr. B 673, 91 (1995); and clinical pharmacokinetics: G. F. Ray et al., J. Pharm. Biomed. Anal. 14, 213 (1995). Review of mechanism of action studies: D. J. Ahnen, Eur. J. Surg. Suppl. 582, 111-114 (1998).

Chemical structure

Properties

mp 194-196°. [α]D -62° (c = 1 in CHCl3).

Therapeutic Category

In treatment of colorectal polyps.