Oxyphenisatine

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Oxyphenisatine
Names
	Preferred IUPAC name 3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one[citation needed]
	Other names Dihydroxydiphenylisatin; Diphenolisatin; Oxyphenisatin
Identifiers
CAS Number	125-13-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL245807 ;
ChemSpider	29053 ;
DrugBank	DB04823 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	D08326 ;
PubChem CID	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
	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

Template:Chembox ECNumber Template:Chembox E number Template:Chembox LogP Template:Chembox pKa Template:Chembox pKb Template:Chembox Pharmacology

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

Overview

Oxyphenisatine (or oxyphenisatin) is a laxative.^[2] It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long term use is associated with liver damage,^[3] and as a result, it was withdrawn in most countries in the early 1970s.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,^[4] 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.^[5]

References

↑ ^1.0 ^1.1 ^1.2 SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
↑ 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.
↑ 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.

Template:Laxatives

[SciFinder-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] 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.

[3] 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.

[4] 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.

[5] 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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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
CAS Number	125-13-3^N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL245807^Y
ChemSpider	29053^Y
DrugBank	DB04823^Y
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	D08326^Y
PubChem CID	31315
UNII	3BT0VQG2GQ^Y
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)^Y Key: SJDACOMXKWHBOW-UHFFFAOYSA-N^Y 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Oxyphenisatine

Overview

References

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