Oxyphenisatine (or oxyphenisatin) is a

laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...

. It is closely related to

bisacodyl Bisacodyl (INN) is an organic compound that is used as a stimulant laxative drug. It works directly on the colon to produce a bowel movement. It is typically prescribed for relief of episodic and chronic constipation and for the management of n ...

sodium picosulfate Sodium picosulfate (INN, also known as sodium picosulphate) is a contact stimulant laxative used as a treatment for constipation or to prepare the large bowel before colonoscopy or surgery. It is sold under the trade names Sodipic Picofast, Laxob ...

, and

phenolphthalein Phenolphthalein ( ) is a chemical compound with the chemical formula, formula carbon, C20hydrogen, H14oxygen, O4 and is often written as "HIn", "HPh", "phph" or simply "Ph" in shorthand notation. Phenolphthalein is often used as an indicator in ...

. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s. The

acetate An acetate is a salt (chemistry), salt formed by the combination of acetic acid with a base (e.g. Alkali metal, alkaline, Alkaline earth metal, earthy, Transition metal, metallic, nonmetallic or radical Radical (chemistry), base). "Acetate" als ...

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

oxyphenisatine acetate was also once used as a laxative. Natural chemical compounds similar to oxyphenisatine may be present in

prune A prune is a dried plum, most commonly from the European plum (''Prunus domestica''). Not all plum species or varieties can be dried into prunes. A prune is the firm-fleshed fruit (plum) of ''Prunus domestica'' varieties that have a high solu ...

s, but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly

neochlorogenic acid Neochlorogenic acid is a natural polyphenol found in some dried fruits and other plant sources, such as peaches. It is an isomer of chlorogenic acid; both of these are members of the caffeoylquinic acid Caffeoylquinic acids (CQA) are compounds com ...

s and

chlorogenic acid Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffe ...

s) and

sorbitol Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol g ...

Synthesis

The ketone group of

isatin Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and ...

(1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties. Oxyphenisatin synthesis

In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has

cathartic In medicine, a cathartic is a substance that ''accelerates'' defecation. This is similar to a laxative, which is a substance that ''eases'' defecation, usually by softening feces. It is possible for a substance to be both a laxative and a cathart ...

properties. * Triacetyldiphenolisatin ( Laxagetten, Unilax, Trisatin), Nicoxyphenisatin & Cinnoxyphenisatin are chemical derivatives.

References

Hepatotoxins Lactams Indolines 2,2-Bis(4-hydroxyphenyl)propanes {{gastrointestinal-drug-stub