Structure via PubChem · Public domain (PubChem)
oxyphenisatin
Sign in to saveAlso known as 3,3-Bis(4-hydroxyphenyl)-oxindole, Oxyphenisatine, Oxiphenisatinum, 3,3-Bis(p-hydroxyphenyl)-2-indolinone, 3,3-Bis(p-hydroxyphenyl)oxindole, Dihydroxyphenoloxindol, 4,4'-Dihydroxydiphenylisatin, 1,3-Dihydro-3,3-bis(4-hydroxyphenyl)-2H-indol-2-one
Oxyphenisatine (or oxyphenisatin) is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s.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.
Chemical data
- Formula
- C20H15NO3
- Molecular weight
- 317.3 g/mol
- IUPAC name
- 3,3-bis(4-hydroxyphenyl)-1H-indol-2-one
- SMILES
- C1=CC=C2C(=C1)C(C(=O)N2)(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O
- InChIKey
- SJDACOMXKWHBOW-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 69.6 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- Constipation
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 317.105
- Has use
- medication
Show 3 more facts
- chemical formula
- C₂₀H₁₅NO₃
- canonical SMILES
- C1=CC=C2C(=C1)C(C(=O)N2)(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O
- defined daily dose
- 10.0
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- Derivatives
- References
Oxyphenisatine (or oxyphenisatin) is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s.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, 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. Oxyphenisatin has cathartic properties.
Excerpted from Wikipedia’s “oxyphenisatin” article, available under the CC BY-SA 4.0 licence.
Available in 10 languages
via Wikidata sitelinks · CC0