9153. Teprenone

Nomenclature

CAS number: 6809-52-5
6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one; geranylgeranylacetone; GGA; E-0671; E36U31; Selbex (Eisai).
C23H38O; mol wt 330.55.
C 83.57%, H 11.59%, O 4.84%.

Description and references

Acyclic polyisoprenoid 2:3 mixture of (5Z,9E,13E) and all trans (5E,9E,13E) isomers. Prepn from geranylgeranyl bromide: L. Ruzicka, L. Castro, Helv. Chim. Acta 28, 590 (1945); from substituted acetylenes: K. Sato et al., J. Org. Chem. 35, 565 (1970). Anti-ulcer and toxicity studies: M. Murakami et al., Arzneim.-Forsch. 31, 799 (1981). In vivo effects on aspirin induced gastric ulcer: eidem, Jpn. J. Pharmacol. 32, 299 (1982); on stress induced gastric ulcer: eidem, ibid. 33, 549 (1983). Mechanism of action studies: Y. Nishizawa et al., Biochem. Biophys. Res. Commun. 103, 706 (1981); K. Oketani et al., Jpn. J. Pharmacol. 33, 593 (1983). Metabolism in rats: Y. Nishizawa et al., Xenobiotica 17, 575 (1987). Determn in serum by GC-MS: M. Tanaka et al., J. Chromatogr. 231, 301 (1982); by HPLC: T. Seki et al., ibid. 424, 410 (1988).

Chemical structure

Properties

Yellow oil, bp0.01 155-160°. d420.5 0.9081. nD20 1.4947.

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative; Cytoprotectant (Gastric)