Description
Ecabet sodium is a new antiulcer agent launched in Japan for the treatment of gastric
ulcer. It has both mucosal-protective and tissue-repairing properties. In rats, it effectively
prevents gastrointestinal lesion formation induced experimentally by EtOH, HCl, NaOH, and
boiling water. The mechanism of action has been suggested to involve inhibition of pepsin
activity in gastric juice by precipitating pepsin in the form of a complex and inactivating
pepsinogen.
Synthesis
Synthesis of sodium (4bS,8R,8aR)-8-carboxy-2-isopropyl-4b,8-dimethyl-4b,5,6,7,8,8a,9,10,10-octahydro-phenanthrene-3-sulfonate from (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-6-sulfo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid The general procedure for the salt was as follows: the feedstock compound (II) (80 g, 0.210 mol) was added to a 25% aqueous solution of sodium isooctanoate (36.6 g, 0.221 mol) and the reaction was stirred for 0.5 to 1 hour. The mixture was then heated until it was completely dissolved and showed clarification, after which it was thermally filtered. The filtrate was cooled to 0°C to 10°C to induce precipitation of a large white solid. The precipitate was separated by filtration and the filter cake was dried under reduced pressure to give the target product (I) as a white solid. The product was characterized as follows: specific spin of +72° (water), moisture content of 18.06%, HPLC purity of more than 99.5%, chemical content of 99.98%, and total yield of 87.5%.
References
[1] Wang Y, et al. Efficacy and safety of ecabet sodium as an adjuvant therapy for Helicobacter pylori eradication: a systematic review and meta-analysis. Helicobacter. 2014 Oct;19(5):372-81. DOI:
10.1111/hel.12136[2] Rah YC, et al. Ecabet sodium alleviates neomycin-induced hair cell damage. Free Radic Biol Med. 2015 Dec;89:1176-83. DOI:
10.1016/j.freeradbiomed.2015.11.007[3] Kenji Kusumoto, et al. Ecabet sodium inhibits Helicobacter pylori lipopolysaccharide-induced activation of NADPH oxidase 1 or apoptosis of guinea pig gastric mucosal cells. Am J Physiol Gastrointest Liver Physiol DOI:
10.1152/ajpgi.00274.2004
