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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyPhenolphthalein
Identification
- Name
- Phenolphthalein
- Accession Number
- DB04824
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Description
Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.
- Structure
Structure for Phenolphthalein (DB04824)
- Synonyms
- 3,3-Bis(4-hydroxyphenyl)phthalide
- Fenolftalein
- Fenolftaleina
- Phenolphtaleine
- Phenolphthaleinum
- Phthalimetten
- phthalin
- Yellow phenolphthalein
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Alophen Tab 60mg Tablet 60 mg Oral Warner Lambert Canada Inc. 1992-12-31 1997-10-10 Canada 
Espotabs Laxative Tablets 90mg Tablet 90 mg Oral Combe Incorporated 1994-12-31 1997-07-24 Canada EX-lax Chocolated Tab 95mg Tablet 95 mg Oral Novartis 1991-12-31 1997-10-10 Canada Feen-A-mint Phenolphthalein Tab 100mg Tablet 100 mg Oral Schering Plough Healthcare Products Canada, A Division Of Schering Canada Inc. 1993-12-31 1997-08-08 Canada Laxative Pills - Tablet Tablet 90 mg Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1996-12-31 1997-08-08 Canada Laxative Tablets Tablet 94 mg Oral Perrigo International 1995-12-31 1997-10-16 Canada Neo Prunex Jam Jelly 100 mg Oral Neolab Inc 1982-12-31 1997-08-12 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Agarol Eml Strawberry Phenolphthalein (65 mg) + Glycerin (200 mg) + Mineral oil (1.6 ml) Emulsion Oral Warner Lambert Canada Inc. 1992-12-31 1997-09-15 Canada Agarol Vanilla Laxative Liq Phenolphthalein (65 mg) + Glycerin (200 mg) + Mineral oil (1.6 ml) Liquid Oral Warner Lambert Canada Inc. 1992-12-31 1997-09-15 Canada Calcium Docuphen Cap Phenolphthalein (65 mg) + Docusate calcium (60 mg) Capsule Oral Pharmascience Inc 1988-12-31 1997-10-10 Canada Correctol Laxative Tab Phenolphthalein (65 mg) + Docusate sodium (100 mg) Tablet Oral Schering Plough Healthcare Products Canada, A Division Of Schering Canada Inc. 1971-12-31 1997-08-08 Canada Doxidan Capsules Phenolphthalein (65 mg) + Docusate calcium (60 mg) Capsule Oral Hoechst Canada Inc. 1987-12-31 1997-08-05 Canada Doxidan Capsules Phenolphthalein (65 mg) + Docusate calcium (60 mg) Capsule Oral Hoechst Roussel Canada Inc. 1994-12-31 1998-08-12 Canada Doxidan Capsules Phenolphthalein (65 mg) + Docusate calcium (60 mg) Capsule Oral Hoechst Marion Roussel 1997-04-21 1997-10-10 Canada EX-lax Light Formula Lax W Stool Soften Tab Phenolphthalein (65 mg) + Docusate sodium (75 mg) Tablet Oral Novartis 1991-12-31 1997-10-10 Canada Laxarol Phenolphthalein (65 mg) + Mineral oil (1.6 ml) Liquid Oral Therapex Division De E Z Em Canada Inc 1985-12-31 1997-07-22 Canada Mucinum Tab Phenolphthalein (75 mg) + Sennosides (40 mg) Tablet Oral Sabex Inc 1978-12-31 1997-10-10 Canada - International/Other Brands
- Agoral / Alophen / Chocolax / Colax / Doxan / Doxidan / Espotabs / Euchessina / Evac-q-kit / Evac-q-kwik / Evac-q-tabs / Evac-u-gen / Evac-v-lax / Ex-lax / Feen-a-mint gum / Feen-a-mint laxative mints / Femilax / Koprol / Lax-pills / Laxcaps / Laxin / Laxogen / LILO / Medilax / Phenolax / Phillips gelcaps / Prulet / Purga / Purgen / Purgophen / Spulmako-lax / Trilax
- Categories
- UNII
- 6QK969R2IF
- CAS number
- 77-09-8
- Weight
- Average: 318.3228
Monoisotopic: 318.089208936 - Chemical Formula
- C20H14O4
- 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
Pharmacology
- Indication
Used for over a century as a laxative.
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UUDP-glucuronosyltransferase 1-9 Not Available Human UNuclear receptor subfamily 1 group I member 2 Not Available Human UNuclear receptor subfamily 1 group I member 3 Not Available Human UEstrogen receptor alpha agonistHuman USex hormone-binding globulin Not Available Human - 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
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenolphthalein. Aclidinium The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Aclidinium. Agmatine The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Agmatine. Alcuronium The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alcuronium. Alfentanil The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alfentanil. Alphacetylmethadol The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alphacetylmethadol. Alphaprodine The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alphaprodine. Amiloride The risk or severity of adverse effects can be increased when Amiloride is combined with Phenolphthalein. Amiodarone The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amiodarone. Amitriptyline The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amitriptyline. - Food Interactions
- Not 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 References
- Not Available
- External Links
- KEGG Drug
- D05456
- KEGG Compound
- C14286
- PubChem Compound
- 4764
- PubChem Substance
- 46506108
- ChemSpider
- 4600
- BindingDB
- 50077844
- ChEBI
- 34914
- ChEMBL
- CHEMBL63857
- PharmGKB
- PA450915
- Wikipedia
- Phenolphthalein
- ATC Codes
- A06AB04 — Phenolphthalein
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Emulsion Oral Tablet Oral 60 mg Tablet Oral 95 mg Tablet Oral 100 mg Liquid Oral Tablet Oral 90 mg Tablet Oral 94 mg Tablet Oral Jelly Oral 100 mg Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 262.5 °C PhysProp water solubility 400 mg/L YALKOWSKY,SH & HE,Y (2003) logP 2.41 HANSCH,C ET AL. (1995), pH 7.4 pKa 9.7 (at 25 °C) MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.00992 mg/mL ALOGPS logP 4.41 ALOGPS logP 4.35 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 9.16 ChemAxon pKa (Strongest Basic) -6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 66.76 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 91.04 m3·mol-1 ChemAxon Polarizability 32.65 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9934 Blood Brain Barrier + 0.81 Caco-2 permeable - 0.6464 P-glycoprotein substrate Non-substrate 0.5296 P-glycoprotein inhibitor I Non-inhibitor 0.9622 P-glycoprotein inhibitor II Non-inhibitor 0.7602 Renal organic cation transporter Non-inhibitor 0.8906 CYP450 2C9 substrate Non-substrate 0.7388 CYP450 2D6 substrate Non-substrate 0.8969 CYP450 3A4 substrate Non-substrate 0.6225 CYP450 1A2 substrate Non-inhibitor 0.778 CYP450 2C9 inhibitor Inhibitor 0.6684 CYP450 2D6 inhibitor Non-inhibitor 0.8938 CYP450 2C19 inhibitor Non-inhibitor 0.7654 CYP450 3A4 inhibitor Non-inhibitor 0.5773 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5636 Ames test Non AMES toxic 0.9267 Carcinogenicity Non-carcinogens 0.9093 Biodegradation Not ready biodegradable 0.9381 Rat acute toxicity 2.3649 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9899 hERG inhibition (predictor II) Non-inhibitor 0.876
Spectra
- Mass Spec (NIST)
- Download (10.4 KB)
- Spectra
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-00fr-2690000000-8c929a0403799e4cd208 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-004i-2950000000-2239a8a809fdd9396eaf 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Taxonomy
- 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
- Benzofuranone / Phthalide / Isobenzofuranone / Isocoumaran / Phenol / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid / Monocyclic benzene moiety / Lactone / Carboxylic acid ester
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenols (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 trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- 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 an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- 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
- 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
- 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
- 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
- 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...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- 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 November 02, 2018 06:06