Explore a selection of our essential drug information below, or:
Identification
- Summary
Phenolphthalein is a drug used for symptomatic relief of constipation and bowel cleansing prior to medical procedures.
- Generic Name
- Phenolphthalein
- DrugBank Accession Number
- DB04824
- Background
Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Phenolphthalein (DB04824)
- Weight
- Average: 318.3228
Monoisotopic: 318.089208936 - Chemical Formula
- C20H14O4
- Synonyms
- 3,3-Bis(4-hydroxyphenyl)phthalide
- Fenolftalein
- Fenolftaleina
- Phenolphtaleine
- Phenolphthalein
- Phenolphthaleinum
- Phthalimetten
- Phthalin
- Yellow phenolphthalein
Pharmacology
- Indication
Used for over a century as a laxative.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Induction of Bowel preparation (bowel cleansing) •••••••••••• •••••• Treatment of Constipation •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UUDP-glucuronosyltransferase 1A9 Not Available Humans UNuclear receptor subfamily 1 group I member 2 Not Available Humans UNuclear receptor subfamily 1 group I member 3 Not Available Humans UEstrogen receptor agonistHumans USex hormone-binding globulin Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The risk or severity of dehydration can be increased when Acetazolamide is combined with Phenolphthalein. Aclidinium The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Aclidinium. Alfentanil The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Alfentanil. Amantadine The therapeutic efficacy of Phenolphthalein can be decreased when used in combination with Amantadine. Amiloride The risk or severity of dehydration can be increased when Amiloride is combined with Phenolphthalein. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Chocolax / Feen-a-mint gum / Feen-a-mint laxative mints
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alophen Tab 60mg Tablet 60 mg / tab Oral Warner Lambert Canada Inc. 1992-12-31 1997-10-10 Canada 
Espotabs Laxative Tablets 90mg Tablet 90 mg / tab Oral Combe Incorporated 1994-12-31 1997-07-24 Canada EX-lax Chocolated Tab 95mg Tablet 95 mg / tab Oral Novartis 1991-12-31 1997-10-10 Canada Feen-A-mint Phenolphthalein Tab 100mg Tablet 100 mg / tab 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 / tab Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1996-12-31 1997-08-08 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Agarol Eml Strawberry Phenolphthalein (65 mg / 5 mL) + Glycerin (200 mg / 5 mL) + Mineral oil (1.6 mL / 5 mL) Emulsion Oral Warner Lambert Canada Inc. 1992-12-31 1997-09-15 Canada Agarol Vanilla Laxative Liq Phenolphthalein (65 mg / 5 mL) + Glycerin (200 mg / 5 mL) + Mineral oil (1.6 mL / 5 mL) Liquid Oral Warner Lambert Canada Inc. 1992-12-31 1997-09-15 Canada Aid-lax Tab Phenolphthalein (100 mg / tab) + Alloin (12 mg / tab) + Frangula purshiana bark (30 mg / tab) + Sodium taurocholate (60 mg / tab) Tablet Oral Nobel Pharm Enr. 1989-12-31 1997-07-31 Canada Alsiline Phenolphthalein (100 mg / tab) + Alloin (12 mg / tab) + Frangula purshiana bark (30 mg / tab) + Sodium taurocholate (60 mg / tab) Tablet Oral Alsi Cie Ltee 1978-12-31 1997-08-08 Canada Bicholate Lilas Tab Phenolphthalein (100 mg) + Alloin (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg) Tablet Oral Sabex Inc 1991-12-31 1997-10-10 Canada
Categories
- ATC Codes
- A06AB04 — Phenolphthalein
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Benzenoid / Benzofuranone / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Isobenzofuranone / Isocoumaran / Lactone
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenols (CHEBI:34914)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6QK969R2IF
- CAS number
- 77-09-8
- 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
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
- 155122
- ChEBI
- 34914
- ChEMBL
- CHEMBL63857
- ZINC
- ZINC000003831317
- PharmGKB
- PA450915
- PDBe Ligand
- FGT
- Wikipedia
- Phenolphthalein
- PDB Entries
- 6gko / 6gyj
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Emulsion Oral Liquid Oral Tablet Oral 60 mg / tab Tablet Oral 95 mg / tab Tablet Oral 100 mg / tab Tablet Oral 50 mg Tablet Oral Tablet Oral 90 mg / tab Tablet Oral 94 mg / tab Tablet Oral 250 mg Tablet, chewable Buccal Jelly Oral 100 mg / 7 g Capsule Oral Tablet Oral 100.000 mg Tablet - 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.2940632 predictedDarkChem Lite v0.1.0 [M-H]- 188.3757632 predictedDarkChem Lite v0.1.0 [M-H]- 173.65251 predictedDeepCCS 1.0 (2019) [M+H]+ 189.6300632 predictedDarkChem Lite v0.1.0 [M+H]+ 188.3625632 predictedDarkChem Lite v0.1.0 [M+H]+ 176.01048 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.2649632 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.3732632 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.14659 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
- Specific Function
- enzyme binding
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1A9
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- Inverse agonist at the canonical form of the receptor. Agonist at isoform 3 of the receptor.
- General 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
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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 factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- androgen binding
- 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. [Article]
Drug created at September 11, 2007 20:27 / Updated at June 19, 2021 00:26