DrugBank: Phenolphthalein (DB04824)

targets (1)

Identification

Name

Phenolphthalein

Accession Number

DB04824

Type

small molecule

Groups

withdrawn

Description

Phenolphthalein was withdrawn in Canada due to concerns with carcinogenicity in 1997.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

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 [czech]
Fenolftaleina [inn-spanish]
Phenolphtaleine [inn-french]
Phenolphthaleinum [inn-latin]
Phenophthalein

Salts

Not Available

Brand names

Name	Company
Agoral
Alophen
Chocolax
Colax
Correctol
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
Phthalimetten
Phthalin
Prulet
Purga
Purgen
Purgophen
Spulmako-lax
Trilax

Brand mixtures

Not Available

Categories

Indicators and Reagents

CAS number

77-09-8

Weight

Average: 318.3228
Monoisotopic: 318.089208936

Chemical Formula

C₂₀H₁₄O₄

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

show (10.4 KB)

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Used for over a century as a laxative.

Pharmacodynamics

Not Available

Mechanism of action

Not Available

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

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	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	9.92e-03 g/l	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	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	91.04	ChemAxon
polarizability	32.65	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D05456
KEGG Compound	C14286
PubChem Compound	4764
PubChem Substance	46506108
ChemSpider	4600
BindingDB	50077844
PharmGKB	PA450915
Wikipedia	http://en.wikipedia.org/wiki/Phenolphthalein

ATC Codes

A06AB04

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. UDP-glucuronosyltransferase 1-9 Pharmacological action: unknown UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols Organism class: human UniProt ID: O60656 Gene: UGT1A9 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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

Targets

1. UDP-glucuronosyltransferase 1-9

Pharmacological action: unknown

UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols

Organism class: human
UniProt ID: O60656 Link_out

Gene: UGT1A9 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Comments

Drug created on September 11, 2007 14:27 / Updated on February 08, 2013 16:23