Details of the Drug

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Constipation DD91.1 Withdrawn from market [1]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
Logarithm of the Partition Coefficient (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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [4]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [4]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [4]
Aldo-keto reductase family 1 member C4 (AKR1C4) OTW2MMOF AK1C4_HUMAN Gene/Protein Processing [4]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [5]
Sex hormone-binding globulin (SHBG) OTPWU5IW SHBG_HUMAN Protein Interaction/Cellular Processes [6]
Thymidylate synthase OTXTG0C7 TYSY_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 2B15 OTABTFU2 UDB15_HUMAN Biotransformations [8]
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] [9]
Midostaurin DMI6E0R Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Midostaurin. Acute myeloid leukaemia [2A60] [9]
Arn-509 DMT81LZ Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Arn-509. Acute myeloid leukaemia [2A60] [9]
Gilteritinib DMTI0ZO Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Gilteritinib. Acute myeloid leukaemia [2A60] [9]
Oliceridine DM6MDCF Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Oliceridine. Acute pain [MG31] [10]
Dronedarone DMA8FS5 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Dronedarone. Angina pectoris [BA40] [9]
Bedaquiline DM3906J Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [9]
Retigabine DMGNYIH Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Retigabine. Behcet disease [4A62] [10]
Eribulin DM1DX4Q Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Eribulin. Breast cancer [2C60-2C6Y] [9]
Bosutinib DMTI8YE Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Bosutinib. Breast cancer [2C60-2C6Y] [9]
PF-04449913 DMSB068 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and PF-04449913. Chronic myelomonocytic leukaemia [2A40] [9]
Pasireotide DMHM7JS Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pasireotide. Cushing syndrome [5A70] [9]
Osilodrostat DMIJC9X Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Osilodrostat. Cushing syndrome [5A70] [10]
Tetrabenazine DMYWQ0O Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Tetrabenazine. Dissociative neurological symptom disorder [6B60] [9]
Deutetrabenazine DMUPFLI Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Deutetrabenazine. Dystonic disorder [8A02] [9]
Fostemsavir DM50ILT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Fostemsavir. Human immunodeficiency virus disease [1C60-1C62] [9]
Rilpivirine DMJ0QOW Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Rilpivirine. Human immunodeficiency virus disease [1C60-1C62] [9]
Crizotinib DM4F29C Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Crizotinib. Lung cancer [2C25] [9]
Ceritinib DMB920Z Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Ceritinib. Lung cancer [2C25] [9]
Osimertinib DMRJLAT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Osimertinib. Lung cancer [2C25] [9]
Selpercatinib DMZR15V Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Selpercatinib. Lung cancer [2C25] [10]
Lumefantrine DM29GAD Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lumefantrine. Malaria [1F40-1F45] [10]
Inotuzumab ozogamicin DMAC130 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Inotuzumab ozogamicin. Malignant haematopoietic neoplasm [2B33] [9]
Vemurafenib DM62UG5 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Vemurafenib. Melanoma [2C30] [9]
LGX818 DMNQXV8 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and LGX818. Melanoma [2C30] [9]
Panobinostat DM58WKG Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Panobinostat. Multiple myeloma [2A83] [9]
Siponimod DM2R86O Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Siponimod. Multiple sclerosis [8A40] [9]
Romidepsin DMT5GNL Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Romidepsin. Mycosis fungoides [2B01] [10]
Nilotinib DM7HXWT Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Nilotinib. Myeloproliferative neoplasm [2A20] [9]
Entrectinib DMMPTLH Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Entrectinib. Non-small cell lung cancer [2C25] [10]
Lofexidine DM1WXA6 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lofexidine. Opioid use disorder [6C43] [9]
Triclabendazole DMPWGBR Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Triclabendazole. Parasitic worm infestation [1F90] [10]
Pimavanserin DMR7IVC Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pimavanserin. Parkinsonism [8A00] [9]
Lefamulin DME6G97 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lefamulin. Pneumonia [CA40] [9]
Degarelix DM3O8QY Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Degarelix. Prostate cancer [2C82] [9]
ABIRATERONE DM8V75C Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and ABIRATERONE. Prostate cancer [2C82] [9]
Enzalutamide DMGL19D Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Enzalutamide. Prostate cancer [2C82] [9]
Iloperidone DM6AUFY Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Iloperidone. Schizophrenia [6A20] [9]
Asenapine DMSQZE2 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Asenapine. Schizophrenia [6A20] [9]
LEE011 DMMX75K Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and LEE011. Solid tumour/cancer [2A00-2F9Z] [9]
Vandetanib DMRICNP Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Vandetanib. Solid tumour/cancer [2A00-2F9Z] [9]
Triptorelin DMTK4LS Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Triptorelin. Solid tumour/cancer [2A00-2F9Z] [9]
Pitolisant DM8RFNJ Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Pitolisant. Somnolence [MG42] [9]
Telavancin DM58VQX Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Telavancin. Staphylococcal/streptococcal disease [1B5Y] [9]
Lenvatinib DMB1IU4 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Lenvatinib. Thyroid cancer [2D10] [9]
Cabozantinib DMIYDT4 Moderate Increased risk of ventricular arrhythmias by the combination of Phenolphthalein and Cabozantinib. Thyroid cancer [2D10] [9]
⏷ 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 Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.
5 Profiling of the Tox21 10K compound library for agonists and antagonists of the estrogen receptor alpha signaling pathway. Sci Rep. 2014 Jul 11;4:5664. doi: 10.1038/srep05664.
6 Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and -fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27.
7 Identification of the binding modes of N-phenylphthalimides inhibiting bacterial thymidylate synthase through X-ray crystallography screening. J Med Chem. 2011 Aug 11;54(15):5454-67.
8 Characterization of a cloned human dihydrotestosterone/androstanediol UDP-glucuronosyltransferase and its comparison to other steroid isoforms. Biochemistry. 1993 Oct 12;32(40):10648-57. doi: 10.1021/bi00091a015.
9 Canadian Pharmacists Association.
10 Cerner Multum, Inc. "Australian Product Information.".