Oxyphenisatine (oroxyphenisatin) is alaxative.[3] It is closely related tobisacodyl,sodium picosulfate, andphenolphthalein. Long-term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s. Theacetatederivative oxyphenisatine acetate was also once used as a laxative.
Natural chemical compounds similar to oxyphenisatine may be present inprunes,[5] but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainlyneochlorogenic acids andchlorogenic acids) andsorbitol.[6] Oxyphenisatin hascathartic properties.
The ketone group ofisatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties.
^Farack, U. M.; Nell, G. (1984). "Mechanism of Action of Diphenolic Laxatives: The Role of Adenylate Cyclase and Mucosal Permeability".Digestion.30 (3):191–194.doi:10.1159/000199105.PMID6548720.
^Baum, H. M.; Sanders, R. G.; Straub, G. J. (1951). "The Occurrence of a Diphenyl Isatin in California Prunes".Journal of the American Pharmaceutical Association.40 (7):348–349.doi:10.1002/jps.3030400713.PMID14850362.
^Stacewicz-Sapuntzakis, M.; Bowen, P. E.; Hussain, E. A.; Damayanti-Wood, B. I.; Farnsworth, N. R. (2001). "Chemical Composition and Potential Health Effects of Prunes: A Functional Food?".Critical Reviews in Food Science and Nutrition.41 (4):251–286.doi:10.1080/20014091091814.PMID11401245.S2CID31159565.
