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Details

Stereochemistry ACHIRAL
Molecular Formula C20H14O4
Molecular Weight 318.3228
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOLPHTHALEIN

SMILES

OC1=CC=C(C=C1)C2(OC(=O)C3=CC=CC=C23)C4=CC=C(O)C=C4

InChI

InChIKey=KJFMBFZCATUALV-UHFFFAOYSA-N
InChI=1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H

HIDE SMILES / InChI

Molecular Formula C20H14O4
Molecular Weight 318.3228
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Phenolphthalein is a chemical compound often used as an indicator in acid-base titrations. For this application, it turns colorless in acidic solutions and pink in basic solutions. In medicine, phenolphtaleine was used as a laxative, but is now being removed from over-the-counter laxatives because of concerns over carcinogenicity. The mechanism of action of phenolphthalein is poorly understood. It is speculated that laxative effect of phenolphthalein in part to be mediated by the efflux of potassium from cells.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FAM-LAX

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
For treatment of constipation, phenolphtalein was administered orally as tablets.
Route of Administration: Oral
In Vitro Use Guide
The transport of 86Rb+ across human colonocyte cells (T84) cultured on trans-well inserts was examined. The T84 cells were cultured until they developed tight junctions and a high trans-epithelial resistance. Phenolphthalein applied to the apical, but not the basolateral, surface of cells at doses 10-40 uM causes the release of 86Rb+ from the apical surface. Basolateral treatment of cells with phenolphthalein had no effect on the release of 86Rb+.
Substance Class Chemical
Record UNII
6QK969R2IF
Record Status Validated (UNII)
Record Version