Oxyphenisatine
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Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one | |
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.004.299 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C20H15NO3 | |
Molar mass | 317.344 g·mol−1 |
log P | 1.398 |
Acidity (pKa) | 9.423 |
Basicity (pKb) | 4.574 |
Pharmacology | |
A06AB01 (WHO) | |
Oral, rectal | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Long-term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s.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] Oxyphenisatin has cathartic properties.
Synthesis
[edit]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.
![](http://upload.wikimedia.org/wikipedia/commons/thumb/5/50/Oxyphenisatin_synthesis.svg/500px-Oxyphenisatin_synthesis.svg.png)
In 1885, it was reported that condensation of isatin with phenol 2 leads to oxyphenisatin (3), which can then also be acetylated to (4).
Derivatives
[edit]- Phenisatin (Triacetyldiphenolisatin, Laxagetten, Unilax, Trisatin)
- Nicoxyphenisatin
- Cinnoxyphenisatin
- Cofisatine [54063-34-2]
References
[edit]- ^ a b c SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
- ^ 21 CFR 216.24
- ^ 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. PMID 6548720.
- ^ Kotha, P.; Rake, M. O.; Willatt, D. (1980). "Liver Damage Induced by Oxyphenisatin". British Medical Journal. 281 (6254): 1530. doi:10.1136/bmj.281.6254.1530. PMC 1714947. PMID 6893676.
- ^ 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. PMID 14850362.
- ^ 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. PMID 11401245. S2CID 31159565.
- ^ Baeyer, A.; Lazarus, M. J. (1885). "Ueber Condensationsproducte des Isatins". Berichte der Deutschen Chemischen Gesellschaft. 18 (2): 2637. doi:10.1002/cber.188501802170.