7877. Prostaglandin E2

Nomenclature

CAS number: 363-24-6
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid; 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid; dinoprostone; PGE2; U-12062; Minprostin E2 (Pharmacia); Prepidil (Pharmacia & Upjohn); Propess (Ferring); Prostin E2 (Pharmacia & Upjohn).
C20H32O5; mol wt 352.47.
C 68.15%, H 9.15%, O 22.70%.

Description and references

The most common and most biologically potent of mammalian prostaglandins. Isoln from sheep prostate: S. Bergstr"om, J. Sj"ovall, GB 851827; eidem, US 3598858 (1960, 1971); from sheep seminal vesicle tissue: S. Bergstr"om et al., Acta Chem. Scand. 16, 501 (1962). Total synthesis of the dl-form: W. P. Schneider, Chem. Commun. 1969, 304; E. J. Corey et al., J. Am. Chem. Soc. 91, 5675 (1969); E. J. Corey et al., Tetrahedron Lett. 1970, 307; W. P. Schneider, DE 2011969 (1970 to Upjohn), C.A. 74, 87486n (1971); J. Fried et al., J. Am. Chem. Soc. 94, 4342 (1972). Synthesis of naturally occurring form: E. J. Corey et al., ibid. 92, 397, 2586 (1970); J. B. Heather et al., Tetrahedron Lett. 1973, 2313; from Plexaura homomalla prostaglandin intermediates: G. L. Bundy et al., J. Am. Chem. Soc. 94, 2123 (1972); W. P. Schneider et al., Chem. Commun. 1973, 254. Biosynthesis: D. A. Van Dorp et al., Biochim. Biophys. Acta 90, 204 (1964); S. Bergstr"om et al., ibid. 207; NL 6505799 (1965 to Unilever), C.A. 65, 7584h (1966). Metabolism: E. Anggard, B. Samuelsson, Mem. Soc. Endocrinol., no. 14, 107 (1966); M. Hamberg, B. Samuelsson, J. Biol. Chem. 246, 6713 (1971). Several reviews in Prostaglandin Symp. Worcester Found. Exp. Biol., P. Ramwell, Ed. (Interscience, New York, 1968). For general refs see Prostaglandins.

Chemical structure

Properties

Natural form, colorless crystals. mp 66-68°. [α]D26 -61° (c = 1 in tetrahydrofuran). Easily dehydrated in soln at pHs <4 or >8.

Therapeutic Category

Oxytocic; abortifacient.

Keywords

Abortifacient/Interceptive; Oxytocic; Prostaglandin/Prostaglandin Analog