IDPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy
Targets (1)
Targets (1)

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Identification
NamePhenolphthalein
Accession NumberDB04824
TypeSmall Molecule
GroupsWithdrawn
Description

Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.

Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone
3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-one
3,3-Bis(4-hydroxyphenyl)phthalide
3,3-Bis(p-hydroxyphenyl)phthalide
Alpha-di(p-hydroxyphenyl)phthalide
Dihydroxyphthalophenone
Fenolftalein
Fenolftaleina
Phenolphtaleine
Phenolphthaleinum
Phenophthalein
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
PhthalimettenNot Available
PhthalinNot Available
PruletNot Available
PurgaNot Available
PurgenNot Available
PurgophenNot Available
Spulmako-laxNot Available
TrilaxNot Available
Brand mixtures
NameLabellerIngredients
Agarol Eml StrawberryWarner Lambert Canada Inc.
  1. Glycerin
  2. Mineral oil
  3. Phenolphthalein
Agarol Vanilla Laxative LiqWarner Lambert Canada Inc.
  1. Glycerin
  2. Mineral oil
  3. Phenolphthalein
Calcium Docuphen CapPharmascience Inc
  1. Docusate
  2. Phenolphthalein
Correctol Laxative TabSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.
  1. Docusate
  2. Phenolphthalein
Doxidan CapsulesHoechst Roussel Canada Inc.
  1. Docusate
  2. Phenolphthalein
EX-lax Light Formula Lax W Stool Soften TabNovartis
  1. Docusate
  2. Phenolphthalein
LaxarolTherapex Division De E Z Em Canada Inc
  1. Mineral oil
  2. Phenolphthalein
Mucinum TabSabex Inc
  1. Phenolphthalein
  2. Sennosides
Phillips' GelcapsSterling Winthrop Inc.
  1. Docusate
  2. Phenolphthalein
Pilules SparkProduits Francais Labs Inc.
  1. Phenolphthalein
  2. Sennosides
Women's Laxative TabletsPerrigo International
  1. Docusate
  2. Phenolphthalein
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
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
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 - , 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

Details
1. UDP-glucuronosyltransferase 1-9
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
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 ]
Drug created on September 11, 2007 14:27 / Updated on June 24, 2017 13:22