Oxyphenisatine

Oxyphenisatine
Names
Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one
Other names
Dihydroxydiphenylisatin;[1] Diphenolisatin;[1] Oxyphenisatin[1]
Identifiers
ATC code A06AB01
125-13-3 
ChEMBL ChEMBL245807 Yes
ChemSpider 29053 Yes
DrugBank DB04823 Yes
EC number 204-728-1
Jmol-3D images Image
Image
KEGG D08326 Yes
PubChem 31315
UNII 3BT0VQG2GQ Yes
Properties
Molecular formula
 C20H15NO3
Molar mass 317.34 g·mol−1
log P 1.398
Acidity (pKa) 9.423
Basicity (pKb) 4.574
Pharmacology
Oral, rectal
Legal status
Except where noted otherwise, data is 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 Long term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s.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]

References

  1. ↑ 1.0 1.1 1.2 SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
  2. ↑ 21 C.F.R. 216.24
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.