3489. Ecabet

Nomenclature

CAS number: 33159-27-2
(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-6-sulfo-1-phenanthrenecarboxylic acid; dehydro-6-sulfoabietic acid; 12-sulfodehydroabietic acid.
C20H28O5S; mol wt 380.50.
C 63.13%, H 7.42%, O 21.02%, S 8.43%.

Description and references

Prepn: L. F. Fieser, W. P. Campbell, J. Am. Chem. Soc. 60, 2631 (1938); H. Wada et al., Chem. Pharm. Bull. 33, 1472 (1985). Metabolism in animals: Y. Ito et al., J. Pharmacobio-Dyn. 14, 533 (1991). Efficacy in healing expt ulcers in rats: Y. Onoda et al., Arzneim.-Forsch. 41, 546 (1991). Gastroprotective effects in rats in comparison with sucralfate, q.v.: M. Kinoshita et al., Dig. Dis. Sci. 40, 661 (1995). Bactericidal activity against Helicobacter pylori: K. Shibata et al., Antimicrob. Agents Chemother. 39, 1295 (1995).

Chemical structure

Properties

As the hemihydrate, [α]D25 +72.4° (c = 2.5 in alcohol).

Derivative

Sodium salt.

Nomenclature

CAS number: 86408-72-2
TA-2711; Gastron (Tanabe).
C20H27NaO5S; mol wt 402.48.
C 59.68%, H 6.76%, Na 5.71%, O 19.88%, S 7.97%.

Properties

Occurs as pentahydrate, mp >300°. [α]D20 +59.4° (c = 0.5).

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative