Oxyphenisatine

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Oxyphenisatine
Oxyphenisatine.png
Other names Dihydroxydiphenylisatin;[1] Diphenolisatin;[1] Oxyphenisatin[1]
Identifiers
CAS number 125-13-3
PubChem 31315
EINECS number 204-728-1
DrugBank DB04823
KEGG D08326
ATC code A06AB01
SMILES Oc1ccc(cc1)C1(C(=O)Nc2ccccc12)c1ccc(O)cc1
InChI InChI=1/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24)
Properties
Molecular formula C20H15NO3
Molar mass 317.34 g mol-1
log P 1.398
Acidity (pKa) 9.423
Basicity (pKb) 4.574
Pharmacology
Routes of
administration
Oral, rectal
Legal status


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Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 Long term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s.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. Template:CodeFedReg
  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. PMID 6548720. doi:10.1159/000199105. 
  4. Kotha, P.; Rake, M. O.; Willatt, D. (1980). "Liver Damage Induced by Oxyphenisatin" (pdf). British Medical Journal. 281 (6254): 1530. PMC 1714947Freely accessible. PMID 6893676. doi:10.1136/bmj.281.6254.1530. 
  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. PMID 14850362. doi:10.1002/jps.3030400713. 
  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. PMID 11401245. doi:10.1080/20014091091814. 

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