Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H14O4 |
| Molecular Weight | 318.3235 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
DescriptionCurator's Comment: description was created based on several sources, including
http://www.sigmaaldrich.com/catalog/product/sial/105945?lang=en®ion=RU | https://www.ncbi.nlm.nih.gov/pubmed/12940878
Curator's Comment: description was created based on several sources, including
http://www.sigmaaldrich.com/catalog/product/sial/105945?lang=en®ion=RU | https://www.ncbi.nlm.nih.gov/pubmed/12940878
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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0002115 |
|||
Target ID: GO:0071435 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | FAM-LAX Approved UseFam-Lax Phenolphthalein Tablets work by increasing bowel movement which helps to empty the contents of the bowel. Fam-Lax Phenolphthalein Tablets are used for the relief of constipation. |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator​
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [Activation 0.7 uM] | ||||
| yes [Activation 7.2 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The evolution of cyclodextrin glucanotransferase product specificity. | 2009-08 |
|
| Examination of seminal stain by HPLC assay of phenolphthalein. | 2009-04 |
|
| On the mechanism of floating and sliding of liquid marbles. | 2009-03-09 |
|
| Hydrolytic fragmentation of seed gums under microwave irradiation. | 2009-03-01 |
|
| Phenolphthalein as a prototype drug for a group of structurally related calcium channel blockers in human platelets. | 2009-03 |
|
| Active oxygen doctors the evidence. | 2009-02 |
|
| Chemical enhancement techniques of bloodstain patterns and DNA recovery after fire exposure. | 2009-01 |
|
| Notch1 is a frequent mutational target in chemically induced lymphoma in mouse. | 2008-12-01 |
|
| The genetics of feto-placental development: a study of acid phosphatase locus 1 and adenosine deaminase polymorphisms in a consecutive series of newborn infants. | 2008-09-03 |
|
| [A new method for safety monitoring of natural dietary supplements--quality profile]. | 2008-07 |
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| Analysis of six synthetic adulterants in herbal weight-reducing dietary supplements by LC electrospray ionization-MS. | 2008-07 |
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| Phenolsulfonphthalein, but not phenolphthalein, inhibits amyloid fibril formation: implications for the modulation of amyloid self-assembly. | 2008-06-03 |
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| Metabolic comparison of radiolabeled aniline- and phenol-phthaleins with (131)I. | 2008-05 |
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| Synthesis and characterization of an amphiphilic cyclodextrin, a micelle with two recognition sites. | 2008-04-15 |
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| Stable RNA markers for identification of blood and saliva stains revealed from whole genome expression analysis of time-wise degraded samples. | 2008-03 |
|
| Pseudo-obstruction with pitch black colon--a very rare presentation of melanosis coli. | 2008-01 |
|
| Modulation of rat intestinal nuclear factor NF-kappaB by gum arabic. | 2008-01 |
|
| The cyclodextrin glycosyltransferase of Paenibacillus pabuli US132 strain: molecular characterization and overproduction of the recombinant enzyme. | 2008 |
|
| Pt(II) and Pd(II) complexes with beta-alanine. | 2008 |
|
| Gene expression-based screening for inhibitors of PDGFR signaling. | 2008 |
|
| The toxicology and carcinogenesis study of phenolphthalein (CAS No. 77-09-8) in genetically modified haploinsufficient p16(Ink4a)/p19(Arf) mice (feed study). | 2007-12 |
|
| Establishment of an early liver fibrosis model by the hydrodynamics-based transfer of TGF-beta1 gene. | 2007-10-19 |
|
| Novel approaches to analysis by flow injection gradient titration. | 2007-09-26 |
|
| Dynamical description of transient x-ray lasers seeded with high-order harmonic radiation through Maxwell-Bloch numerical simulations. | 2007-09-21 |
|
| Particle size of fillers affects permeability of polymethylmethacrylate. | 2007-08 |
|
| Sucrose, xylitol, and erythritol increase PMMA permeability for depot antibiotics. | 2007-08 |
|
| Amino terminal domains of human UDP-glucuronosyltransferases (UGT) 2B7 and 2B15 associated with substrate selectivity and autoactivation. | 2007-05-01 |
|
| Properties of stimulus-dependent synchrony in retinal ganglion cells. | 2007-03-20 |
|
| [An improved method of photometric determination of cyclodextrin glucanotransferase activity]. | 2007-03-10 |
|
| Identification of the human liver UDP-glucuronosyltransferase involved in the metabolism of p-ethoxyphenylurea (dulcin). | 2007-03 |
|
| Evaluation of six presumptive tests for blood, their specificity, sensitivity, and effect on high molecular-weight DNA. | 2007-01 |
|
| A full automatic device for sampling small solution volumes in photometric titration procedure based on multicommuted flow system. | 2007 |
|
| [Current problems in the quality control of pharmaceutical preparations manufactured in pharmacies III. Investigation of theophilline containing suppositories]. | 2007 |
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| Bidirectional and colorimetric recognition of sodium and potassium ions. | 2006-12-07 |
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| Optimizing use of opiates in the management of cancer pain. | 2006-12 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Profiling of the resin glycoside content of Mexican jalap roots with purgative activity. | 2006-10 |
|
| Enhancement of absorption by gum arabic in a model of gastrointestinal dysfunction. | 2006-08 |
|
| A comparison of the presumptive luminol test for blood with four non-chemiluminescent forensic techniques. | 2006-04-29 |
|
| Activity measurement of a 176Lu sample using coincidence peaks and Monte Carlo simulations. | 2006-04-11 |
|
| Phenolphthalein and bisacodyl: assessment of genotoxic and carcinogenic responses in heterozygous p53 (+/-) mice and syrian hamster embryo (SHE) assay. | 2006-04 |
|
| Technical note: Determination of acidity in whole raw milk: comparison of results obtained by two different analytical methods. | 2006-03 |
|
| Tibolone metabolism in human liver is catalyzed by 3alpha/3beta-hydroxysteroid dehydrogenase activities of the four isoforms of the aldo-keto reductase (AKR)1C subfamily. | 2006-03 |
|
| Sequential injection titration with spectrophotometric detection for the assay of acidity in fruit juices. | 2006-01 |
|
| Expression and significance of nerve growth factor receptor p75 in rats' cathartic colonic wall. | 2006 |
|
| Laxative-induced burns in a child. | 2006 |
|
| [Clinical observation on moving cupping therapy combined with moxibustion for treatment of senile habitual constipation]. | 2005-12 |
|
| Study of the concentration and separation of cadmium with microcrystalline phenolphthalein modified by crystal violet. | 2004-11-15 |
|
| Carbon analysis for inspecting carbonation of concrete using a TEA CO2 laser-induced plasma. | 2004-08 |
|
| Sequential injection redox or acid-base titration for determination of ascorbic acid or acetic acid. | 2002-12-06 |
Sample Use Guides
For treatment of constipation, phenolphtalein was administered orally as tablets.
Route of Administration:
Oral
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+.
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A06AB04
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201-384-4
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PHENOLPHTHALEIN
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5768-87-6
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SUPERSEDED |
ACTIVE MOIETY
