Phenolphthalein

Identification

Generic Name
Phenolphthalein
DrugBank Accession Number
DB04824
Background

Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 318.3228
Monoisotopic: 318.089208936
Chemical Formula
C20H14O4
Synonyms
  • 3,3-Bis(4-hydroxyphenyl)phthalide
  • Fenolftalein
  • Fenolftaleina
  • Phenolphtaleine
  • Phenolphthalein
  • Phenolphthaleinum
  • Phthalimetten
  • Phthalin
  • Yellow phenolphthalein

Pharmacology

Indication

Used for over a century as a laxative.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-glucuronosyltransferase 1-9Not AvailableHumans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
UNuclear receptor subfamily 1 group I member 3Not AvailableHumans
UEstrogen receptor alpha
agonist
Humans
USex hormone-binding globulinNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenolphthalein.
AclidiniumThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Aclidinium.
AlfentanilThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alfentanil.
AmantadineThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Phenolphthalein.
AmiodaroneThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amiodarone.
AmitriptylineThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amitriptyline.
AmlodipineThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amlodipine.
AmobarbitalThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amobarbital.
AmoxapineThe therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amoxapine.
Interactions
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Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Chocolax / Feen-a-mint gum / Feen-a-mint laxative mints
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alophen Tab 60mgTabletOralWarner Lambert Canada Inc.1992-12-311997-10-10Canada flag
Espotabs Laxative Tablets 90mgTabletOralCombe Incorporated1994-12-311997-07-24Canada flag
EX-lax Chocolated Tab 95mgTabletOralNovartis1991-12-311997-10-10Canada flag
Feen-A-mint Phenolphthalein Tab 100mgTabletOralSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.1993-12-311997-08-08Canada flag
Laxative Pills - TabletTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1996-12-311997-08-08Canada flag
Laxative TabletsTabletOralPerrigo International1995-12-311997-10-16Canada flag
Neo Prunex JamJellyOralNeolab Inc1982-12-311997-08-12Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Agarol Eml StrawberryPhenolphthalein (65 mg) + Glycerin (200 mg) + Mineral oil (1.6 ml)EmulsionOralWarner Lambert Canada Inc.1992-12-311997-09-15Canada flag
Agarol Vanilla Laxative LiqPhenolphthalein (65 mg) + Glycerin (200 mg) + Mineral oil (1.6 ml)LiquidOralWarner Lambert Canada Inc.1992-12-311997-09-15Canada flag
Aid-lax TabPhenolphthalein (100 mg) + Alloin (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralNobel Pharm Enr.1989-12-311997-07-31Canada flag
AlsilinePhenolphthalein (100 mg) + Alloin (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralAlsi Cie Ltee1978-12-311997-08-08Canada flag
Bicholate Lilas TabPhenolphthalein (100 mg) + Alloin (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralSabex Inc1991-12-311997-10-10Canada flag
Bilex TabPhenolphthalein (100 mg) + Alloin (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralBiodo Enrg1978-12-311997-10-10Canada flag
Calcium Docuphen CapPhenolphthalein (65 mg) + Docusate calcium (60 mg)CapsuleOralPharmascience Inc1988-12-311997-10-10Canada flag
Carters Little Pills TabPhenolphthalein (16 mg) + Alloin (8 mg)TabletOralCarter Products, Division Of Carter Wallace Ns Inc.1978-12-311997-08-14Canada flag
Correctol Laxative TabPhenolphthalein (65 mg) + Docusate sodium (100 mg)TabletOralSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.1971-12-311997-08-08Canada flag
Doulax TabPhenolphthalein (97.2 mg) + Frangula purshiana bark (32.4 mg)TabletOralLes Laboratoires Bio SantÉ Inc.1983-12-311998-01-14Canada flag

Categories

ATC Codes
A06AB04 — Phenolphthalein
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Benzofuranones
Direct Parent
Benzofuranones
Alternative Parents
Phthalides / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Lactones / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Benzenoid / Benzofuranone / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Isobenzofuranone / Isocoumaran / Lactone
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenols (CHEBI:34914)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6QK969R2IF
CAS number
77-09-8
InChI Key
KJFMBFZCATUALV-UHFFFAOYSA-N
InChI
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
IUPAC Name
3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one
SMILES
OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1

References

Synthesis Reference

Hershel B. Prindle, George E. Ham, "Preparation of phenolphthalein using cation exchange resins and aryl phosphites." U.S. Patent US4252725, issued March, 1966.

US4252725
General References
Not Available
KEGG Drug
D05456
KEGG Compound
C14286
PubChem Compound
4764
PubChem Substance
46506108
ChemSpider
4600
BindingDB
50077844
RxNav
155122
ChEBI
34914
ChEMBL
CHEMBL63857
ZINC
ZINC000003831317
PharmGKB
PA450915
PDBe Ligand
FGT
Wikipedia
Phenolphthalein
PDB Entries
6gko / 6gyj

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
EmulsionOral
LiquidOral
TabletOral
TabletOral
Tablet, chewableBuccal
JellyOral
CapsuleOral
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)262.5 °CPhysProp
water solubility400 mg/LYALKOWSKY,SH & HE,Y (2003)
logP2.41HANSCH,C ET AL. (1995), pH 7.4
pKa9.7 (at 25 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.00992 mg/mLALOGPS
logP4.41ALOGPS
logP4.35ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.04 m3·mol-1ChemAxon
Polarizability32.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier+0.81
Caco-2 permeable-0.6464
P-glycoprotein substrateNon-substrate0.5296
P-glycoprotein inhibitor INon-inhibitor0.9622
P-glycoprotein inhibitor IINon-inhibitor0.7602
Renal organic cation transporterNon-inhibitor0.8906
CYP450 2C9 substrateNon-substrate0.7388
CYP450 2D6 substrateNon-substrate0.8969
CYP450 3A4 substrateNon-substrate0.6225
CYP450 1A2 substrateNon-inhibitor0.778
CYP450 2C9 inhibitorInhibitor0.6684
CYP450 2D6 inhibitorNon-inhibitor0.8938
CYP450 2C19 inhibitorNon-inhibitor0.7654
CYP450 3A4 inhibitorNon-inhibitor0.5773
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5636
Ames testNon AMES toxic0.9267
CarcinogenicityNon-carcinogens0.9093
BiodegradationNot ready biodegradable0.9381
Rat acute toxicity2.3649 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9899
hERG inhibition (predictor II)Non-inhibitor0.876
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-00fr-2690000000-8c929a0403799e4cd208
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-2950000000-2239a8a809fdd9396eaf
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Uesawa Y, Staines AG, Lockley D, Mohri K, Burchell B: Identification of the human liver UDP-glucuronosyltransferase involved in the metabolism of p-ethoxyphenylurea (dulcin). Arch Toxicol. 2007 Mar;81(3):163-8. Epub 2006 Aug 5. [PubMed:16897040]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [PubMed:20869355]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Inverse agonist at the canonical form of the receptor. Agonist at isoform 3 of the receptor.
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [PubMed:20869355]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Curator comments
Phenolphthalein competes with estradiol for the binding site and induces elevated levels of progesterone receptor in the MCF-7 cells at higher concentrations.
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Ravdin PM, van Beurden M, Jordan VC: Estrogenic effects of phenolphthalein on human breast cancer cells in vitro. Breast Cancer Res Treat. 1987;9(2):151-4. [PubMed:3620717]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Drug created on September 11, 2007 20:27 / Updated on April 30, 2021 13:06