A primary prostaglandin; easily crystallized from purified biological extracts. Isoln from sheep seminal vesicle tissue, and structure: Bergstrom et al., Acta Chem. Scand. 16, 501 (1962); eidem, J. Biol. Chem. 238, 3555 (1963). Enzymic conversion from 8,11,14-eicosatrienoic acid: Nugteren et al., Rec. Trav. Chim. 85, 405 (1966). Synthesis of the dl-form: Corey et al., J. Am. Chem. Soc. 90, 3245, 3247 (1968); Schneider et al., ibid. 5895; 91, 5372 (1969); Axen et al., Chem. Commun. 1969, 303; Taub et al., ibid. 1970, 1258; Slates et al., ibid. 1972, 304; Kuo et al., Tetrahedron Lett. 1972, 5317; Taub et al., Tetrahedron 29, 1447 (1973); Miyano, Stealey, Chem. Commun. 1973, 180; Finch et al., J. Org. Chem. 38, 4412 (1973). Synthesis of natural form: Corey et al., J. Am. Chem. Soc. 91, 535 (1969); 92, 2586 (1970); Sih et al., ibid. 94, 3643 (1972); 95, 1676 (1973); Schaaf, Corey, J. Org. Chem. 37, 2921 (1974); Slates et al., Tetrahedron 30, 819 (1974). Metabolism in guinea pigs: Anggard, Samuelsson, J. Biol. Chem. 239, 4097 (1964). Metabolism in humans: Hamberg, Samuelsson, ibid. 246, 6713 (1971). Review of biological activities: Berti et al., Prog. Biochem. Pharmacol. 3, 110 (1967). Comparative pharmacology with respect to other prostaglandins: Weeks, Annu. Rev. Pharmacol. 12, 317 (1972). Clinical use in neonates with cyanotic congenital heart disease: P. M. Olley et al., Adv. Prostaglandin Thromboxane Res. 7, 913 (1980). Use in non-atherosclerotic vasculopathy: D. L. Wooster et al., J. Am. Med. Assoc. 245, 1846 (1981). Clinical trials in impotence: O. I. Linet, F. G. Ogrinc, N. Engl. J. Med. 334, 873 (1996); H. Padma-Nathan et al., ibid. 336, 1 (1997).
Vasodilator (peripheral). In treatment of male erectile dysfunction.
Prostaglandin/Prostaglandin Analog; Vasodilator (Peripheral)