Oxyphenisatine
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Oxyphenisatine
| Oxyphenisatine | |
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3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one[citation needed] |
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| Identifiers | |
| CAS number | 125-13-3  |
| PubChem | 31315 |
| ChemSpider | 29053  |
| UNII | 3BT0VQG2GQ |
| EC number | 204-728-1 |
| DrugBank | DB04823 |
| KEGG | D08326 |
| ChEMBL | CHEMBL245807 |
| ATC code | A06 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C20NH15O3 |
| log P | 1.398 |
| Acidity (pKa) | 9.423 |
| Basicity (pKb) | 4.574 |
| Pharmacology | |
| Routes of administration |
Oral, rectal |
| Legal status |
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 Long term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s.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]
References
- ^ a b c SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
- ^ 21 C.F.R. 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" (pdf). British Medical Journal 281 (6254): 1530. doi:10.1136/bmj.281.6254.1530. PMC 1714947. PMID 6893676. http://www.bmj.com/highwire/filestream/332472/field_highwire_article_pdf/0/1530.1.full.pdf.
- ^ 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.
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