General Information of Drug (ID: DM5SICT)

Drug Name
Phenolphthalein
Synonyms
phenolphthalein; 77-09-8; Phthalimetten; Phthalin; Euchessina; Phenolax; Purgophen; Espotabs; Koprol; Trilax; Laxogen; Purga; Lilo; Spulmako-lax; Feen-A-Mint Gum; Chocolax; Purgen; 3,3-Bis(4-hydroxyphenyl)phthalide; Ex-Lax; Fenolftalein; Correctol; Alophen; Medilax; Doxidan; Colax; Laxin; FemiLax; Dihydroxyphthalophenone; Phillips Gelcaps; 3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone; Lax-Pills; Evac-Q-Tabs; Evac-Q-Kwik; Evac-U-Gen; Evac-Q-Kit; 1(3H)-Isobenzofuranone, 3,3-bis(4-hydroxyphenyl)-; Phenolphtaleine; Fenolftaleina; Phenophthalein
Indication
Disease Entry ICD 11 Status REF
Constipation DD91.1 Withdrawn from market [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 318.3
Topological Polar Surface Area (xlogp) 3.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C20H14O4
IUPAC Name
3,3-bis(4-hydroxyphenyl)-2-benzofuran-1-one
Canonical SMILES
C1=CC=C2C(=C1)C(=O)OC2(C3=CC=C(C=C3)O)C4=CC=C(C=C4)O
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
InChIKey
KJFMBFZCATUALV-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4764
ChEBI ID
CHEBI:34914
CAS Number
77-09-8
DrugBank ID
DB04824
TTD ID
D03FDT
VARIDT ID
DR01166
INTEDE ID
DR1277

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)
Main DME
DEYGVN4 UD11_HUMAN Substrate [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Phenolphthalein (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ivosidenib DM8S6T7 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Ivosidenib. Acute myeloid leukaemia [2A60] [24]
Midostaurin DMI6E0R Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Midostaurin. Acute myeloid leukaemia [2A60] [24]
Arn-509 DMT81LZ Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Arn-509. Acute myeloid leukaemia [2A60] [24]
Gilteritinib DMWQ4MZ Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Gilteritinib. Acute myeloid leukaemia [2A60] [24]
Oliceridine DM6MDCF Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Oliceridine. Acute pain [MG31] [25]
Dronedarone DMA8FS5 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Dronedarone. Angina pectoris [BA40] [24]
Bedaquiline DM3906J Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [24]
Retigabine DMGNYIH Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Retigabine. Behcet disease [4A62] [25]
Eribulin DM1DX4Q Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Eribulin. Breast cancer [2C60-2C6Y] [24]
Bosutinib DMTI8YE Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Bosutinib. Breast cancer [2C60-2C6Y] [24]
PF-04449913 DMSB068 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and PF-04449913. Chronic myelomonocytic leukaemia [2A40] [24]
Pasireotide DMHM7JS Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pasireotide. Cushing syndrome [5A70] [24]
Osilodrostat DMIJC9X Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Osilodrostat. Cushing syndrome [5A70] [25]
Tetrabenazine DMYWQ0O Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Tetrabenazine. Dissociative neurological symptom disorder [6B60] [24]
Deutetrabenazine DMUPFLI Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Deutetrabenazine. Dystonic disorder [8A02] [24]
Fostemsavir DM50ILT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Fostemsavir. Human immunodeficiency virus disease [1C60-1C62] [24]
Rilpivirine DMJ0QOW Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Rilpivirine. Human immunodeficiency virus disease [1C60-1C62] [24]
Crizotinib DM4F29C Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Crizotinib. Lung cancer [2C25] [24]
Ceritinib DMB920Z Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Ceritinib. Lung cancer [2C25] [24]
Osimertinib DMRJLAT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Osimertinib. Lung cancer [2C25] [24]
Selpercatinib DMZR15V Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Selpercatinib. Lung cancer [2C25] [25]
Lumefantrine DM29GAD Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lumefantrine. Malaria [1F40-1F45] [25]
Inotuzumab ozogamicin DMAC130 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Inotuzumab ozogamicin. Malignant haematopoietic neoplasm [2B33] [24]
Vemurafenib DM62UG5 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Vemurafenib. Melanoma [2C30] [24]
LGX818 DMNQXV8 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and LGX818. Melanoma [2C30] [24]
Panobinostat DM58WKG Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Panobinostat. Multiple myeloma [2A83] [24]
Siponimod DM2R86O Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Siponimod. Multiple sclerosis [8A40] [24]
Romidepsin DMT5GNL Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Romidepsin. Mycosis fungoides [2B01] [25]
Nilotinib DM7HXWT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Nilotinib. Myeloproliferative neoplasm [2A20] [24]
Entrectinib DMMPTLH Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Entrectinib. Non-small cell lung cancer [2C25] [25]
Lofexidine DM1WXA6 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lofexidine. Opioid use disorder [6C43] [24]
Triclabendazole DMPWGBR Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Triclabendazole. Parasitic worm infestation [1F90] [25]
Pimavanserin DMR7IVC Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pimavanserin. Parkinsonism [8A00] [24]
Lefamulin DME6G97 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lefamulin. Pneumonia [CA40] [24]
Degarelix DM3O8QY Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Degarelix. Prostate cancer [2C82] [24]
ABIRATERONE DM8V75C Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and ABIRATERONE. Prostate cancer [2C82] [24]
Enzalutamide DMGL19D Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Enzalutamide. Prostate cancer [2C82] [24]
Iloperidone DM6AUFY Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Iloperidone. Schizophrenia [6A20] [24]
Asenapine DMSQZE2 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Asenapine. Schizophrenia [6A20] [24]
LEE011 DMMX75K Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and LEE011. Solid tumour/cancer [2A00-2F9Z] [24]
Vandetanib DMRICNP Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Vandetanib. Solid tumour/cancer [2A00-2F9Z] [24]
Triptorelin DMTK4LS Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Triptorelin. Solid tumour/cancer [2A00-2F9Z] [24]
Pitolisant DM8RFNJ Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pitolisant. Somnolence [MG42] [24]
Telavancin DM58VQX Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Telavancin. Staphylococcal/streptococcal disease [1B5Y] [24]
Lenvatinib DMB1IU4 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lenvatinib. Thyroid cancer [2D10] [24]
Cabozantinib DMIYDT4 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Cabozantinib. Thyroid cancer [2D10] [24]
⏷ Show the Full List of 46 DDI Information of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Biliary excretion of phenolphthalein sulfate in rats. Pharmacology. 2003 Aug;68(4):177-82.
3 Inhibition of UDP-glucuronyltransferase activity in rat liver microsomes by pyrimidine derivatives. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1995 Nov;112(3):321-5.
4 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
5 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
6 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
7 UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
8 Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
9 Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36.
10 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
11 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
12 Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
13 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
14 Involvement of the drug transporters p glycoprotein and multidrug resistance-associated protein Mrp2 in telithromycin transport. Antimicrob Agents Chemother. 2006 Jan;50(1):80-7.
15 Dose-dependent disposition of methotrexate in Abcc2 and Abcc3 gene knockout murine models. Drug Metab Dispos. 2011 Nov;39(11):2155-61.
16 Mammalian multidrug-resistance proteins (MRPs). Essays Biochem. 2011 Sep 7;50(1):179-207.
17 Enhancing chemosensitivity in oral squamous cell carcinoma by lentivirus vector-mediated RNA interference targeting EGFR and MRP2. Oncol Lett. 2016 Sep;12(3):2107-2114.
18 Multidrug resistance associated protein 2 mediates transport of prostaglandin E2. Liver Int. 2006 Apr;26(3):362-8.
19 Lentivirus-mediated RNAi silencing targeting ABCC2 increasing the sensitivity of a human nasopharyngeal carcinoma cell line against cisplatin. J Transl Med. 2008 Oct 4;6:55.
20 Effect of acetaminophen on expression and activity of rat liver multidrug resistance-associated protein 2 and P-glycoprotein. Biochem Pharmacol. 2004 Aug 15;68(4):791-8.
21 Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7.
22 Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63.
23 Multidrug Resistance-Associated Protein 2 (MRP2) Mediated Transport of Oxaliplatin-Derived Platinum in Membrane Vesicles. PLoS One. 2015 Jul 1;10(7):e0130727.
24 Canadian Pharmacists Association.
25 Cerner Multum, Inc. "Australian Product Information.".