Prostacyclin
Title: Prostacyclin
CAS Registry Number: 35121-78-9
CAS Name: (5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid
Additional Names: (5Z)-9-deoxy-6,9a-epoxy-D5-PGF1a; epoprostenol; prostaglandin I2; prostaglandin X; PGI2; PGX
Manufacturers' Codes: U-53217
Molecular Formula: C20H32O5
Molecular Weight: 352.47
Percent Composition: C 68.15%, H 9.15%, O 22.70%
Literature References: A prostaglandin produced by enzymatic transformation of prostaglandin endoperoxides (PGG2, PGH2), which dilates blood vessels and is approximately 30 times more potent than prostaglandin E1, q.v., in inhibiting platelet aggregation. Evidence for its occurrence during biosynthetic conversion of arachidonic acid by rat stomach homogenates: C. Pace-Asciak, L. S. Wolfe, Biochemistry 10, 3657 (1971). Isoln from microsomes of pig and rabbit aorta by J. R. Vane and co-workers: S. Moncada et al., Nature 263, 663 (1976). Prepn: S. Moncada, N. Whittaker, DE 2720999; S. Moncada, US 4539333 (1977, 1985 both to Wellcome Found.). PGI2 is also synthesized in bovine coronary arteries as well as human arteries and veins: eidem, Lancet 1, 18 (1977); G. J. Dusting et al., Prostaglandins 13, 3 (1977); by cultured human and bovine endothelial cells: B. B. Weksler et al., Proc. Natl. Acad. Sci. USA 74, 3922 (1977); by pig aortic endothelial cells: D. E. MacIntyre et al., Nature 271, 549 (1978). It has been suggested that endoperoxides released by platelets can be converted to PGI2 by vascular tissue and that a balance between formation of PGI2 and release of thromboxane A2, q.v., which induces platelet aggregation, controls the formation of thrombi in blood vessels. It has also been postulated that PGI2 acts to stimulate platelet adenylate cyclase and to prevent the action of thrombi on phospholipid breakdown as well as platelet aggregation. Structure: R. A. Johnson et al., Prostaglandins 12, 915 (1976). Synthesis: E. J. Corey et al., J. Am. Chem. Soc. 99, 3006 (1977); of sodium salt and stereochemistry: R. A. Johnson et al., ibid. 4182. Additional syntheses: I. Tomoskozi et al., Tetrahedron Lett. 1977, 2627; N. Whittaker, ibid. 2805; K. Nicolaou, Chem. Commun. 1977, 630. Synthesis of the 5E-isomer: E. J. Corey et al., Tetrahedron Lett. 1977, 3529. Chemical stability in aq solns: M. J. Cho, M. A. Allen, Prostaglandins 15, 943 (1978). Biosynthetic study: V. Tomasi et al., Nature 273, 670 (1978). Biological properties: R. J. Gryglewski et al., Prostaglandins 12, 685 (1976). Preliminary clinical study: A. E. S. Gimson et al., Lancet 1, 173 (1980). Antimetastatic effects: K. V. Honn et al., Science 212, 1270 (1981); eidem, ibid. 217 542 (1982). Preliminary study of effect of PGX infusion in patients with acute myocardial infarction: O. Edhag et al., N. Engl. J. Med. 308, 1032 (1983). Review of biological properties: S. Moncada, J. R. Vane, Clin. Sci. 61, 369-372 (1981); of therapeutic potential: eidem, Adv. Pharmacol. Ther. 4, 215-233 (1982); of physiological role: J. R. Vane et al., Int. Rev. Exp. Pathol. 23, 161-207 (1982). General reviews: S. Moncada, J. R. Vane, Fed. Proc. 38, 66-71 (1979); J. C. McGiff, Annu. Rev. Pharmacol. Toxicol. 21, 479-509 (1981); S. Moncada et al., Adv. Pharmacol. Ther. 6, 39-47 (1982). Books: Prostacyclin, J. R. Vane, S. Bergstrom, Eds. (Raven Press, New York, 1979) 453 pp; Prostaglandins in Cardiovascular and Renal Function, A. Scriabine et al., Eds. (Spectrum Publications, New York, 1980) 498 pp.
Properties: Chemically unstable in aq soln. Hydrolyzes to 6-oxo-PGF1a. Half-life at 4° is approx 14.5 min when total phosphate is 0.165 M. Anti-aggregating activity disappears within 0.25 min on boiling or within 10 min at 37°.
 
Derivative Type: Sodium salt
CAS Registry Number: 61849-14-7
Manufacturers' Codes: U-53217A
Trademarks: Flolan (GSK)
Molecular Formula: C20H31NaO5
Molecular Weight: 374.45
Percent Composition: C 64.15%, H 8.34%, Na 6.14%, O 21.36%
Properties: Hygroscopic, free-flowing white powder. Stable for 2 months if kept dry at -30°.
 
Therap-Cat: Platelet aggregation inhibitor.
Keywords: Prostaglandin/Prostaglandin Analog.

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