Title: Prostaglandin E2
CAS Registry Number: 363-24-6
CAS Name: (5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
Additional Names: 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid; dinoprostone; PGE2
Manufacturers' Codes: U-12062
Trademarks: Minprostin E2 (Pharmacia); Prepidil (Pharmacia & Upjohn); Propess (Ferring); Prostin E2 (Pharmacia & Upjohn)
Molecular Formula: C20H32O5
Molecular Weight: 352.47
Percent Composition: C 68.15%, H 9.15%, O 22.70%
Literature References: The most common and most biologically potent of mammalian prostaglandins. Isoln from sheep prostate: S. Bergström, J. Sjövall, GB 851827; eidem, US 3598858 (1960, 1971); from sheep seminal vesicle tissue: S. Bergström 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. Bergström 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.
Properties: Natural form, colorless crystals. mp 66-68°. [a]D26 -61° (c = 1 in tetrahydrofuran). Easily dehydrated in soln at pHs <4 or >8.
Melting point: mp 66-68°
Optical Rotation: [a]D26 -61° (c = 1 in tetrahydrofuran)
Therap-Cat: Oxytocic; abortifacient.
Keywords: Abortifacient/Interceptive; Oxytocic; Prostaglandin/Prostaglandin Analog. |