Oxyphenisatine

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Oxyphenisatine
Kekulé, skeletal formula of oxyphenisatine
Names
Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one[citation needed]
Other names
Dihydroxydiphenylisatin;[1] Diphenolisatin;[1] Oxyphenisatin[1]
Identifiers
125-13-3 N
3D model (Jmol) Interactive image
Interactive image
ChEMBL ChEMBL245807 YesY
ChemSpider 29053 YesY
DrugBank DB04823 YesY
ECHA InfoCard 100.004.299
EC Number 204-728-1
KEGG D08326 YesY
PubChem 31315
UNII 3BT0VQG2GQ YesY
Properties
C20H15NO3
Molar mass 317.34 g·mol−1
log P 1.398
Acidity (pKa) 9.423
Basicity (pKb) 4.574
Pharmacology
A06AB01 (WHO)
Legal status
Oral, rectal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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 Long-term use is associated with liver damage,[4] and as a result, it was withdrawn in most countries in the early 1970s.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[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.

Oxyphenisatin synthesis:[7]

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[edit]

  1. ^ a b c 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 1714947Freely accessible. 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. 
  7. ^ Baeyer, A.; Lazarus, M. J. (1885). "Ueber Condensationsproducte des Isatins". Berichte der deutschen chemischen Gesellschaft. 18 (2): 2637. doi:10.1002/cber.188501802170.