Trimoprostil
Title: Trimoprostil
CAS Registry Number: 69900-72-7
CAS Name: (5Z,11a,13E,15R)-15-Hydroxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid
Additional Names: (Z)-7-[(1R,2R,3R)-2-[(E)-(3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-3-methyl-5-oxocyclopentyl]-5-heptenoic acid; nat-11R,16,16-trimethyl-15R-hydroxy-9-oxoprosta-cis-5-trans-13-dienoic acid; 11R,16,16-trimethyl-(11-desoxyprostaglandin E2); 11-deoxy-11a,16,16-trimethyl-PGE2; TM-PGE2
Manufacturers' Codes: Ro-21-6937
Trademarks: Ulstar (Roche)
Molecular Formula: C23H38O4
Molecular Weight: 378.55
Percent Composition: C 72.97%, H 10.12%, O 16.91%
Literature References: Synthetic prostaglandin E2 analog with antisecretory activity. Prepn: G. W. Holland et al., DE 2437622; eidem, US 4052446; US 4190587 (1975, 1977, 1980 all to Hoffmann-La Roche). Pharmacology: D. E. Wilson, S. L. Winter, Prostaglandins 16, 127 (1978); S. P. Lee et al., Eur. J. Clin. Invest. 17, 1 (1987). Effect on bicarbonate secretion: M. Feldman, J. Clin. Invest. 72, 295 (1983); on inhibition of gastric acid secretion: R. J. Wills et al., Clin. Pharmacol. Ther. 37, 113 (1985). Metabolism: S. J. Kolis et al., Drug Metab. Dispos. 14, 465 (1986). Clinical pharmacokinetics: R. J. Wills et al., J. Clin. Pharmacol. 26, 48 (1986). Clinical evaluation: H. G. Dammann et al., Arzneim.-Forsch. 36, 500 (1986). Multicenter clinical comparison with cimetidine, q.v.: K. D. Bardhan et al., Scand. J. Gastroenterol. 23, 134 (1988); with aldioxa, q.v.: A. Ishimori et al., Acta Ther. 15, 27 (1989). Toxicity study: M. Shimizu et al., Shin'yaku to Rinsho 35, 2199 (1986), C.A. 106, 150180e (1987).
Properties: Colorless oil. [a]D -51.54° (c = 1 in CHCl3). LD50 in mice, rats (mg/kg): 41, 23 orally; 70, 21 i.p.; 68, 29 s.c. (Shimizu).
Optical Rotation: [a]D -51.54° (c = 1 in CHCl3)
Toxicity data: LD50 in mice, rats (mg/kg): 41, 23 orally; 70, 21 i.p.; 68, 29 s.c. (Shimizu)
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative; Prostaglandin/Prostaglandin Analog.

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