Identification
NamePhenolphthalein
Accession NumberDB04824
TypeSmall Molecule
GroupsWithdrawn
Description

Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.

Structure
Thumb
Synonyms
3,3-Bis(4-hydroxyphenyl)phthalide
Fenolftalein
Fenolftaleina
Phenolphtaleine
Phenolphthaleinum
Phthalimetten
phthalin
Yellow phenolphthalein
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alophen Tab 60mgTablet60 mgOralWarner Lambert Canada Inc.1992-12-311997-10-10Canada
Espotabs Laxative Tablets 90mgTablet90 mgOralCombe Incorporated1994-12-311997-07-24Canada
EX-lax Chocolated Tab 95mgTablet95 mgOralNovartis1991-12-311997-10-10Canada
Feen-A-mint Phenolphthalein Tab 100mgTablet100 mgOralSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.1993-12-311997-08-08Canada
Laxative Pills - TabletTablet90 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1996-12-311997-08-08Canada
Laxative TabletsTablet94 mgOralPerrigo International1995-12-311997-10-16Canada
Neo Prunex JamJelly100 mgOralNeolab Inc1982-12-311997-08-12Canada
Unapproved/Other Products Not Available
International Brands
NameCompany
AgoralNot Available
AlophenNot Available
ChocolaxNot Available
ColaxNot Available
DoxanNot Available
DoxidanNot Available
EspotabsNot Available
EuchessinaNot Available
Evac-q-kitNot Available
Evac-q-kwikNot Available
Evac-q-tabsNot Available
Evac-u-genNot Available
Evac-v-laxNot Available
Ex-laxNot Available
Feen-a-mint gumNot Available
Feen-a-mint laxative mintsNot Available
FemilaxNot Available
KoprolNot Available
Lax-pillsNot Available
LaxcapsNot Available
LaxinNot Available
LaxogenNot Available
LILONot Available
MedilaxNot Available
PhenolaxNot Available
Phillips gelcapsNot Available
PruletNot Available
PurgaNot Available
PurgenNot Available
PurgophenNot Available
Spulmako-laxNot Available
TrilaxNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Agarol Eml StrawberryEmulsionOralWarner Lambert Canada Inc.1992-12-311997-09-15Canada
Agarol Vanilla Laxative LiqLiquidOralWarner Lambert Canada Inc.1992-12-311997-09-15Canada
Calcium Docuphen CapCapsuleOralPharmascience Inc1988-12-311997-10-10Canada
Correctol Laxative TabTabletOralSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.1971-12-311997-08-08Canada
Doxidan CapsulesCapsuleOralHoechst Roussel Canada Inc.1994-12-311998-08-12Canada
EX-lax Light Formula Lax W Stool Soften TabTabletOralNovartis1991-12-311997-10-10Canada
LaxarolLiquidOralTherapex Division De E Z Em Canada Inc1985-12-311997-07-22Canada
Mucinum TabTabletOralSabex Inc1978-12-311997-10-10Canada
Phillips' GelcapsCapsuleOralSterling Winthrop Inc.1993-12-311996-09-10Canada
Pilules SparkTabletOralProduits Francais Labs Inc.1982-12-311997-05-30Canada
Women's Laxative TabletsTabletOralPerrigo International1995-12-311997-10-10Canada
Categories
UNII6QK969R2IF
CAS number77-09-8
WeightAverage: 318.3228
Monoisotopic: 318.089208936
Chemical FormulaC20H14O4
InChI KeyKJFMBFZCATUALV-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
Pharmacology
Indication

Used for over a century as a laxative.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
UDP-glucuronosyltransferase 1-9ProteinunknownNot AvailableHumanO60656 details
Nuclear receptor subfamily 1 group I member 2ProteinunknownNot AvailableHumanO75469 details
Nuclear receptor subfamily 1 group I member 3ProteinunknownNot AvailableHumanQ14994 details
Estrogen receptor alphaProteinunknown
agonist
HumanP03372 details
Sex hormone-binding globulinProteinunknownNot AvailableHumanP04278 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
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 ReferencesNot Available
External Links
ATC CodesA06AB04 — Phenolphthalein
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
EmulsionOral
TabletOral60 mg
TabletOral95 mg
TabletOral100 mg
LiquidOral
TabletOral90 mg
TabletOral94 mg
TabletOral
JellyOral100 mg
CapsuleOral
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-2950000000-2239a8a809fdd9396eafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00fr-2690000000-8c929a0403799e4cd208View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzofurans
Direct ParentBenzofuranones
Alternative ParentsPhthalides / 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
SubstituentsBenzofuranone / Phthalide / Isobenzofuranone / Isocoumaran / Phenol / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid / Monocyclic benzene moiety / Lactone / Carboxylic acid ester
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsphenols (CHEBI:34914 )

Targets

Kind
Protein
Organism
Human
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 transferase activity but acts as a negative regulator of isoform 1.
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
Human
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 and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and is...
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
Human
Pharmacological action
unknown
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 responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
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
Human
Pharmacological action
unknown
Actions
agonist
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
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
Human
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, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
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 14:27 / Updated on September 01, 2017 11:22