Oxyphenisatine
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Names | |
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Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one[citation needed]
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Other names | |
Identifiers | |
125-13-3 ![]() |
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ChEMBL | ChEMBL245807 ![]() |
ChemSpider | 29053 ![]() |
DrugBank | DB04823 ![]() |
EC Number | 204-728-1 |
Jmol 3D model | Interactive image Interactive image |
KEGG | D08326 ![]() |
PubChem | 31315 |
UNII | 3BT0VQG2GQ ![]() |
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Properties | |
C20H15NO3 | |
Molar mass | 317.34 g·mol−1 |
log P | 1.398 |
Acidity (pKa) | 9.423 |
Basicity (pKb) | 4.574 |
Pharmacology | |
ATC code | A06 |
Legal status |
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Oral, rectal | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Oxyphenisatine (or oxyphenisatin) is a laxative.[3] It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative.
Natural chemical compounds similar to oxyphenisatine may be present in prunes,[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 (mainly neochlorogenic acids and chlorogenic acids) and sorbitol.[6]
Synthesis
The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties.
![](/w/images/thumb/5/50/Oxyphenisatin_synthesis.svg/700px-Oxyphenisatin_synthesis.svg.png)
In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has cathartic properties.
References
- ↑ 1.0 1.1 1.2 SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
- ↑ 21 C.F.R. 216.24
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