Arbaprostil

Title: Arbaprostil
CAS Registry Number: 55028-70-1
CAS Name: (5Z,11a,13E,15R)-11,15-Dihydroxy-15-methyl-9-oxoprosta-5,13-dien-1-oic acid
Additional Names: (15R)-15-methylprostaglandin E2; (15R)-15-methyl-PGE2; (E,Z)-(1R,2R,3R)-7-[3-hydroxy-2-[(3R)-(3-hydroxy-3-methyl-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid
Manufacturers' Codes: U-42842
Molecular Formula: C21H34O5
Molecular Weight: 366.49
Percent Composition: C 68.82%, H 9.35%, O 21.83%
Literature References: Antisecretory, cytoprotective derivative of prostaglandin E2, q.v. Prepn: G. L. Bundy et al., DE 2121980; G. L. Bundy, US 3804889 (1971, 1974 both to Upjohn). Synthetic studies: G. Bundy et al., Ann. N.Y. Acad. Sci. 180, 76 (1971); E. W. Yankee, G. Bundy, J. Am. Chem. Soc. 94, 3651 (1972). Synthesis of R- and S-methyl esters: E. W. Yankee et al., ibid. 96, 5865 (1974). HPLC separation of epimers: R. K. Lustgarten, J. Pharm. Sci. 65, 1533 (1976); G. E. Peng, V. K. Sood, J. Liq. Chromatogr. 6, 1499 (1983). Pharmacology: J. R. Weeks et al., J. Pharmacol. Exp. Ther. 186, 67 (1973). Comparative activity of epimers: A. Robert, E. W. Yankee, Proc. Soc. Exp. Biol. Med. 148, 1155 (1975). Kinetics of epimerization: M. V. Merritt, G. E. Bronson, J. Am. Chem. Soc. 100, 1891 (1978). Clinical study in duodenal ulcers: G. Vantrappen et al., Gastroenterology 83, 357 (1982); in prevention of aspirin-induced gastric mucosal injury: D. A. Gilbert et al., ibid. 86, 339 (1984).
Derivative Type: (15S)-Methyl ester
Molecular Formula: C22H36O5
Molecular Weight: 380.52
Percent Composition: C 69.44%, H 9.54%, O 21.02%
Properties: Colorless oil, [a]D -79° (c = 1.3 in chloroform). uv max (basic ethanol): 278 nm (e = 25250).
Optical Rotation: [a]D -79° (c = 1.3 in chloroform)
Absorption maximum: uv max (basic ethanol): 278 nm (e = 25250)
Derivative Type: (15R)-Methyl ester
Molecular Formula: C22H36O5
Molecular Weight: 380.52
Percent Composition: C 69.44%, H 9.54%, O 21.02%
Properties: Colorless oil, [a]D -74° (c = 1.0 in chloroform). uv max (basic ethanol): 278 nm (e = 25200).
Optical Rotation: [a]D -74° (c = 1.0 in chloroform)
Absorption maximum: uv max (basic ethanol): 278 nm (e = 25200)
Arbekacin Arborescin Arbutamine Arbutin Ardeparin