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
CAS Number	125-13-3
ChEMBL	ChEMBL245807
ChemSpider	29053
DrugBank	DB04823
EC Number	204-728-1
Jmol interactive 3D	Image Image
KEGG	D08326
PubChem	31315
UNII	3BT0VQG2GQ
InChI InChI=1S/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) Key: SJDACOMXKWHBOW-UHFFFAOYSA-N 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) Key: SJDACOMXKWHBOW-UHFFFAOYAU
SMILES Oc1ccc(cc1)C1(C(=O)Nc2ccccc12)c1ccc(O)cc1 OC1=CC=C(C=C1)C1(C(=O)NC2=C1C=CC=C2)C1=CC=C(O)C=C1
Properties
Chemical formula	C20H15NO3
Molar mass	317.34 g·mol^−1
log P	1.398
Acidity (pKa)	9.423
Basicity (pKb)	4.574
Pharmacology
ATC code	A06AB01
Legal status	Withdrawn[2]
Routes of administration	Oral, rectal
Except where otherwise noted, data are 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 Long term use is associated with liver damage,^[4] and as a result, it was withdrawn in most countries in the early 1970s.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]

Synthesis

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

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