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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Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.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
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
External Identifiers 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
Neo Prunex Jamjam100 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.
Agarol Vanilla Laxative LiqWarner Lambert Canada Inc.
LaxarolTherapex Division De E Z Em Canada Inc
Mucinum TabSabex Inc
Phillips' GelcapsSterling Winthrop Inc.
Pilules SparkProduits Francais Labs Inc.
SaltsNot Available
Categories
UNII6QK969R2IF
CAS number77-09-8
WeightAverage: 318.3228
Monoisotopic: 318.089208936
Chemical FormulaC20H14O4
InChI KeyInChIKey=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
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
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
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 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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Emulsionoral
Tabletoral60 mg
Liquidoral
Tabletoral
Jamoral100 mg
Capsuleoral
Tablet
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)
Spectra
Spectrum TypeDescriptionSplash Key
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
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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 ]
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Drug created on September 11, 2007 14:27 / Updated on August 17, 2016 12:24