Oxyphenisatine

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 Long-term use is associated with liver damage,^[4] and as a result, it was withdrawn in most countries in the early 1970s.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.

Quick facts Names, Identifiers ...

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 N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL245807 Y
ChemSpider	29053 Y
DrugBank	DB04823 Y
ECHA InfoCard	100.004.299
EC Number	204-728-1
KEGG	D08326 Y
PubChem CID	31315
UNII	3BT0VQG2GQ Y
CompTox Dashboard (EPA)	DTXSID5044528
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	317.344 g·mol−1
log P	1.398
Acidity (pKa)	9.423
Basicity (pKb)	4.574
Pharmacology
ATC code	A06AB01 (WHO)
Routes of administration	Oral, rectal
Legal status	Withdrawn[2]
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

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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] Oxyphenisatin has cathartic properties.