1793. Carbenoxolone

Nomenclature

CAS number: 5697-56-3
(3β,20β)-3-(3-Carboxy-1-oxopropoxy)-11-oxoolean-12-en-29-oic acid; 3β-hydroxy-11-oxoolean-12-en-30-oic acid hydrogen succinate; 3-O-(β-carboxypropionyl)-11-oxo-18β-olean-12-en-30-oic acid; 18β-glycyrrhetic acid hydrogen succinate; carbenoxalone.
C34H50O7; mol wt 570.76.
C 71.55%, H 8.83%, O 19.62%.

Description and references

Anti-inflammatory glucocorticoid related to enoxolone, q.v. Prepn: Gottfried, Baxendale, GB 843133; US 3070623 (1960, 1961 to Biorex). Monograph: Carbenoxolone Sodium, J. M. Robson, F. M. Sullivan, Eds. (Butterworths, London, 1969) 263 pp. Symposium on clinical efficacy: Scand. J. Gastroenterol. 15, Suppl. 65, 1-121 (1980). Effect on gastric prostaglandin levels in humans: J. Rask-Madsen et al., Eur. J. Clin. Invest. 13, 351 (1983); P. Minuz et al., Pharmacol. Res. Commun. 16, 875 (1984). Comprehensive description: S. Pindado et al., Anal. Profiles Drug Subs. Excip. 24, 1-43 (1996).

Chemical structure

Properties

Cream-colored crystals, mp 291-294°. [α]D20 +128° (chloroform).

Derivative

Disodium salt.

Nomenclature

CAS number: 7421-40-1
Bioplex (Thames); Bioral (SKB); Neogel (Hexal); Sanodin; Ulcus-Tablinen (Sanorania).
C34H48Na2O7; mol wt 614.72.
C 66.43%, H 7.87%, Na 7.48%, O 18.22%.

Properties

Creamy-white solid. Freely sol in water. Insol in chloroform, ether. pKa1 4.18; pKa2 5.52. uv max (water): 260 nm (Ecm1% 172). LD50 in male mice (mg/kg): 198 i.v.; 120 i.p.; in male rats (mg/kg): 3200 orally (Robson, Sullivan).

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative; Cytoprotectant (Gastric)