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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Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.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
Synonyms
SynonymLanguageCode
3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranoneNot AvailableNot Available
3,3-Bis(4-hydroxyphenyl)-2-benzofuran-1(3H)-oneNot AvailableNot Available
3,3-Bis(4-hydroxyphenyl)phthalideNot AvailableNot Available
3,3-Bis(p-hydroxyphenyl)phthalideNot AvailableNot Available
Alpha-di(p-hydroxyphenyl)phthalideNot AvailableNot Available
DihydroxyphthalophenoneNot AvailableNot Available
FenolftaleinCzechNot Available
FenolftaleinaSpanishINN
PhenolphtaleineFrenchINN
PhenolphthaleinumLatinINN
PhenophthaleinNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Correctoltablet, coated5 mgoralMSD Consumer Care, Inc.2014-07-31Not AvailableUs
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 mixturesNot Available
SaltsNot Available
Categories
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentBenzofuranones
Alternative Parents
Substituents
  • Phthalide
  • Benzofuranone
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed for over a century as a laxative.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateInhibitor0.6684
CYP450 2D6 substrateNon-inhibitor0.8938
CYP450 2C19 substrateNon-inhibitor0.7654
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, coatedoral5 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point262.5 °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
Spectra
Mass Spec (NIST)Download (10.4 KB)
SpectraMS1D NMR
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. UDP-glucuronosyltransferase 1-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-9 O60656 Details

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

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Drug created on September 11, 2007 14:27 / Updated on September 16, 2013 17:25