Oxyphenisatine

Template:Chembox header2 \| Oxyphenisatine
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
Template:Chembox header2 \| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Oxyphenisatine (or oxyphenisatin) is a laxative.^[1] It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long term use is associated with liver damage,^[2] and as a result, it was withdrawn in most countries in the early 1970s.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,^[3] 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.^[4]

References

↑ 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

[1] 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.

[2] 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.

[3] 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.

[4] 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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Oxyphenisatine

References

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