PHENOLPHTHALEIN

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H14O4
Molecular Weight	318.3235
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2(OC(=O)C3=CC=CC=C23)C4=CC=C(O)C=C4

InChI

InChIKey=KJFMBFZCATUALV-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H14O4
Molecular Weight	318.3235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://monographs.iarc.fr/ENG/Monographs/vol76/mono76-15.pdf
Curator's Comment: description was created based on several sources, including http://www.sigmaaldrich.com/catalog/product/sial/105945?lang=en®ion=RU | https://www.ncbi.nlm.nih.gov/pubmed/12940878

Phenolphthalein is a chemical compound often used as an indicator in acid-base titrations. For this application, it turns colorless in acidic solutions and pink in basic solutions. In medicine, phenolphtaleine was used as a laxative, but is now being removed from over-the-counter laxatives because of concerns over carcinogenicity. The mechanism of action of phenolphthalein is poorly understood. It is speculated that laxative effect of phenolphthalein in part to be mediated by the efflux of potassium from cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
store-operated calcium entry 4 Target ID: GO:0002115 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19247192	Blocker 555
potassium ion export 1 Target ID: GO:0071435 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12940878	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Constipation 112 Sources: https://www.drugs.com/mmx/phenolphthalein.html	Curative		Approved 8583	FAM-LAX Approved Use Fam-Lax Phenolphthalein Tablets work by increasing bowel movement which helps to empty the contents of the bowel. Fam-Lax Phenolphthalein Tablets are used for the relief of constipation.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	activator 23

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT2B15 236 UGT1A9 423

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 2141	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/23611293/	yes [Activation 0.7 uM]
CYP2C9 2497	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/23611293/	yes [Activation 7.2 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16897040/	yes
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17223084/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-00053	http://www.3bsc.com/index/pro_info.php?id=20265
AA Blocks	AA003TLJ	http://www.aablocks.com/goods/Goods/detail?id=AA003TLJ
Aaron Chemicals	AR003UDB	http://www.aaronchem.com/77-09-8
abcr GmbH	AB118438	http://www.abcr.com/shop/en/AB118438
abcr GmbH	AB208414	http://www.abcr.com/shop/en/AB208414
abcr GmbH	AB208415	http://www.abcr.de/shop/en/AB208415
abcr GmbH	AB208416	http://www.abcr.com/shop/en/AB208416
abcr GmbH	AB355006	http://www.abcr.com/shop/en/AB355006
Acadechem	ACDS-033204	http://www.acadechemical.com/product/107903
Achemo Scientific Limited	AC-34291	http://www.achemo.com/product_view.asp?ID=132052
Acros Organics	AC147710025	https://www.fishersci.com/shop/products/phenolphthalein-indicator-acros-organics/AC147710025
Acros Organics	AC147711000	https://www.fishersci.com/shop/products/phenolphthalein-indicator-acros-organics-1/AC147711000
Acros Organics	AC147715000	https://www.fishersci.com/shop/products/phenolphthalein-indicator-acros-organics-1/AC147715000
Acros Organics	AC417180026	https://www.fishersci.com/shop/products/phenolphthalein-for-analysis-acs-acros-organics/AC417180026
Acros Organics	AC417181000	https://www.fishersci.com/shop/products/phenolphthalein-for-analysis-acs-acros-organics-1/AC417181000
Alfa Aesar	38703	https://www.alfa.com/en/catalog/038703/
Alfa Aesar	38704	https://www.alfa.com/en/catalog/038704/
Alfa Aesar	38705	https://www.alfa.com/en/catalog/038705/
Alfa Aesar	A17135	https://www.alfa.com/en/catalog/A17135/
Alfa Aesar	J61785	https://www.alfa.com/en/catalog/J61785/
Alichem	19146207	http://www.alichem.com/en/products/77-09-8.html
Ark Pharm	AK130019	http://www.arkpharminc.com/products/77-09-8.html
Aronis	ARONIS002962	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=4626
Aurora Fine Chemicals LLC	K00.417.972	http://online.aurorafinechemicals.com/info?ID=K00.417.972
Aurum Pharmatech LLC	NE46883	http://www.Aurumpharmatech.com/Product/ProductDetails/NE46883
Aurum Pharmatech LLC	T8172	http://www.Aurumpharmatech.com/Product/ProductDetails/T8172
Avantor Inc	101182-052	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101182-052
Avantor Inc	200013-970	https://us.vwr.com/store/product/7515288/phenolphthalein-98-5-pure-indicator-grade
Avantor Inc	700005-602	https://us.vwr.com/store/product/7829636/phenolphthalein-powder-acs
Avantor Inc	700005-604	https://us.vwr.com/store/product/7829636/phenolphthalein-powder-acs
Avantor Inc	700005-606	https://us.vwr.com/store/product/7829636/phenolphthalein-powder-acs
BioSynth	Q-201555	https://www.biosynth.com/en/products/life-science/dyes-stains-indicators-labels/products/Q-201555.html
BLD Pharm	BD105915	http://www.bldpharm.com/products/77-09-8.html
BOC Sciences	77-09-8	https://www.bocsci.com/phenolphthalein-cas-77-09-8-item-13570.html
BroadPharm	BP-30100	http://www.broadpharm.com/web/product.php?catalog=BP-30100
Capot Chemical	7084	http://www.capotchem.com/en/7084.htm
Capot Chemical	PubChem7084	http://www.capotchem.com/en/7084.htm
Chem Scene	CS-8152	http://www.chemscene.com/77-09-8.html
ChemMol	30103872	http://www.chemmol.com/chemmol/30103872.html
ChemMol	49416706	http://www.chemmol.com/chemmol/49416706.html
Chemspace	CSSB00000764093	https://chem-space.com/CSSB00000764093
Clearsynth	CS-O-11712	https://www.clearsynth.com/en/CSO11712.html
CSNpharm	CSN10103	https://www.csnpharm.com/products/phenolphthalein.html
DC Chemicals	DC34141	http://www.dcchemicals.com//product_show-Phenolphthalein.html
Enamine	Z57233591	https://www.enaminestore.com/catalog/Z57233591
Finetech	FT-0659094	http://www.finetechnology-ind.com/prod/detail/pub/77-09-8.html
Fisher Chemical	P79100	https://www.fishersci.com/shop/products/phenolphthalein-certified-acs-fisher-chemical-2/p-180259
Fisher Chemical	P79500	https://www.fishersci.com/shop/products/phenolphthalein-certified-acs-fisher-chemical-2/p-180259
Fisher Chemical	SP621	https://www.fishersci.com/shop/products/phenolphthalein-solution-alcoholic-1-0-fisher-chemical-2/p-213667
Fisher Chemical	SP62500	https://www.fishersci.com/shop/products/phenolphthalein-solution-alcoholic-1-0-fisher-chemical-2/p-213667
Glentham Life Sciences	GT9951	http://www.glentham.com/products/product/GT9951/
Huateng Pharma	F94596	https://en.huatengsci.com/products/intermediates/
Lab Network	LN00195715	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195715
LGC Standards	DRE-C16027000	https://www.lgcstandards.com/US/en/p/DRE-C16027000
LGC Standards	LGCFOR3351.00	https://www.lgcstandards.com/US/en/p/LGCFOR3351.00
LGC Standards	MM3351.00	https://www.lgcstandards.com/US/en/p/MM3351.00
Matrix Scientific	134418	https://www.matrixscientific.com/134418.html
mcule	MCULE-5232154932	https://mcule.com/MCULE-5232154932/
MedChem Express	HY-D0211	https://www.medchemexpress.com/Phenolphthalein.html
MuseChem	R045102	https://www.musechem.com/product/R045102.html
Oakwood	99714	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=130763&ExtHyperLink=1
Renno Tech	RL04943	http://www.rennotech.com/product_show.asp?id=5192
Sigma-Aldrich	105945_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/105945?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1524908_USP	https://www.sigmaaldrich.com/catalog/product/usp/1524908?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	16019_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/16019?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	24-1440_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/241440?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	24-1450_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/241450?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017547	http://www.sinfoobiotech.com/product/1020945
Smolecule	S539449	http://www.smolecule.com/products/s539449
Smolecule	S793324	https://www.smolecule.com/products/s793324
TCI (Tokyo Chemical Industry)	P0094	http://www.tcichemicals.com/eshop/en/us/commodity/P0094/index.html
TCI (Tokyo Chemical Industry)	P0700	http://www.tcichemicals.com/eshop/en/us/commodity/P0700/index.html
TCI (Tokyo Chemical Industry)	P0701	http://www.tcichemicals.com/eshop/en/us/commodity/P0701/index.html
TCI (Tokyo Chemical Industry)	P0702	http://www.tcichemicals.com/eshop/en/us/commodity/P0702/index.html
THE BioTek	bt-279495	https://www.thebiotek.com/product/inhibitors/bt-279495
THE BioTek	bt-461368	https://www.thebiotek.com/product/others/bt-461368
VladaChem	VL143765	https://www.vladachem.com/product.php?products=77-09-8
VladaChem	VL164244	https://www.vladachem.com/product.php?products=77-09-8
VladaChem	VL166721	https://www.vladachem.com/product.php?products=77-09-8
VladaChem	VL167946	https://www.vladachem.com/product.php?products=77-09-8
VladaChem	VL263953-100G	https://www.vladachem.com/product.php?products=77-09-8
Yuhao Chemical	LL0074	http://www.chemyuhao.com/77-09-8.html

PubMed

Title	Date	PubMed
The evolution of cyclodextrin glucanotransferase product specificity.	2009-08	19367403
Examination of seminal stain by HPLC assay of phenolphthalein.	2009-04	19342276
On the mechanism of floating and sliding of liquid marbles.	2009-03-09	19177484
Hydrolytic fragmentation of seed gums under microwave irradiation.	2009-03-01	19135082
Phenolphthalein as a prototype drug for a group of structurally related calcium channel blockers in human platelets.	2009-03	19247192
Active oxygen doctors the evidence.	2009-02	18936905
Chemical enhancement techniques of bloodstain patterns and DNA recovery after fire exposure.	2009-01	19018938
Notch1 is a frequent mutational target in chemically induced lymphoma in mouse.	2008-12-01	18798262
The genetics of feto-placental development: a study of acid phosphatase locus 1 and adenosine deaminase polymorphisms in a consecutive series of newborn infants.	2008-09-03	18768081
[A new method for safety monitoring of natural dietary supplements--quality profile].	2008-07	19035183
Analysis of six synthetic adulterants in herbal weight-reducing dietary supplements by LC electrospray ionization-MS.	2008-07	18569001
Phenolsulfonphthalein, but not phenolphthalein, inhibits amyloid fibril formation: implications for the modulation of amyloid self-assembly.	2008-06-03	18457421
Metabolic comparison of radiolabeled aniline- and phenol-phthaleins with (131)I.	2008-05	18482686
Synthesis and characterization of an amphiphilic cyclodextrin, a micelle with two recognition sites.	2008-04-15	18341360
Stable RNA markers for identification of blood and saliva stains revealed from whole genome expression analysis of time-wise degraded samples.	2008-03	17579879
Pseudo-obstruction with pitch black colon--a very rare presentation of melanosis coli.	2008-01	18269120
Modulation of rat intestinal nuclear factor NF-kappaB by gum arabic.	2008-01	17486449
The cyclodextrin glycosyltransferase of Paenibacillus pabuli US132 strain: molecular characterization and overproduction of the recombinant enzyme.	2008	18704190
Pt(II) and Pd(II) complexes with beta-alanine.	2008	18528519
Gene expression-based screening for inhibitors of PDGFR signaling.	2008	18312689
The toxicology and carcinogenesis study of phenolphthalein (CAS No. 77-09-8) in genetically modified haploinsufficient p16(Ink4a)/p19(Arf) mice (feed study).	2007-12	18784766
Establishment of an early liver fibrosis model by the hydrodynamics-based transfer of TGF-beta1 gene.	2007-10-19	17949486
Novel approaches to analysis by flow injection gradient titration.	2007-09-26	17903467
Dynamical description of transient x-ray lasers seeded with high-order harmonic radiation through Maxwell-Bloch numerical simulations.	2007-09-21	17930505
Particle size of fillers affects permeability of polymethylmethacrylate.	2007-08	17762329
Sucrose, xylitol, and erythritol increase PMMA permeability for depot antibiotics.	2007-08	17549030
Amino terminal domains of human UDP-glucuronosyltransferases (UGT) 2B7 and 2B15 associated with substrate selectivity and autoactivation.	2007-05-01	17223084
Properties of stimulus-dependent synchrony in retinal ganglion cells.	2007-03-20	18093370
[An improved method of photometric determination of cyclodextrin glucanotransferase activity].	2007-03-10	17345870
Identification of the human liver UDP-glucuronosyltransferase involved in the metabolism of p-ethoxyphenylurea (dulcin).	2007-03	16897040
Evaluation of six presumptive tests for blood, their specificity, sensitivity, and effect on high molecular-weight DNA.	2007-01	17209919
A full automatic device for sampling small solution volumes in photometric titration procedure based on multicommuted flow system.	2007	18317510
[Current problems in the quality control of pharmaceutical preparations manufactured in pharmacies III. Investigation of theophilline containing suppositories].	2007	17933266
Bidirectional and colorimetric recognition of sodium and potassium ions.	2006-12-07	17134275
Optimizing use of opiates in the management of cancer pain.	2006-12	18360655
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Profiling of the resin glycoside content of Mexican jalap roots with purgative activity.	2006-10	17067162
Enhancement of absorption by gum arabic in a model of gastrointestinal dysfunction.	2006-08	16943452
A comparison of the presumptive luminol test for blood with four non-chemiluminescent forensic techniques.	2006-04-29	16645959
Activity measurement of a 176Lu sample using coincidence peaks and Monte Carlo simulations.	2006-04-11	16603370
Phenolphthalein and bisacodyl: assessment of genotoxic and carcinogenic responses in heterozygous p53 (+/-) mice and syrian hamster embryo (SHE) assay.	2006-04	16373391
Technical note: Determination of acidity in whole raw milk: comparison of results obtained by two different analytical methods.	2006-03	16507678
Tibolone metabolism in human liver is catalyzed by 3alpha/3beta-hydroxysteroid dehydrogenase activities of the four isoforms of the aldo-keto reductase (AKR)1C subfamily.	2006-03	16339391
Sequential injection titration with spectrophotometric detection for the assay of acidity in fruit juices.	2006-01	16429794
Expression and significance of nerve growth factor receptor p75 in rats' cathartic colonic wall.	2006	17054585
Laxative-induced burns in a child.	2006	16996446
[Clinical observation on moving cupping therapy combined with moxibustion for treatment of senile habitual constipation].	2005-12	16419707
Study of the concentration and separation of cadmium with microcrystalline phenolphthalein modified by crystal violet.	2004-11-15	18969688
Carbon analysis for inspecting carbonation of concrete using a TEA CO2 laser-induced plasma.	2004-08	18070383
Sequential injection redox or acid-base titration for determination of ascorbic acid or acetic acid.	2002-12-06	18968850

Patents

Sample Use Guides

In Vivo Use Guide

For treatment of constipation, phenolphtalein was administered orally as tablets.

Route of Administration: Oral

In Vitro Use Guide

The transport of 86Rb+ across human colonocyte cells (T84) cultured on trans-well inserts was examined. The T84 cells were cultured until they developed tight junctions and a high trans-epithelial resistance. Phenolphthalein applied to the apical, but not the basolateral, surface of cells at doses 10-40 uM causes the release of 86Rb+ from the apical surface. Basolateral treatment of cells with phenolphthalein had no effect on the release of 86Rb+.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:08:49 GMT 2025` Edited by `admin` on `Wed Apr 02 07:08:49 GMT 2025`
Record UNII	6QK969R2IF
Record Status	`FAILED`
Record Version

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Related Record Type

YSD58V84XK

NO NAME

(not present in database)

Alternative Definition

Name

Type

Language

PHENOLPHTHALEIN,WHITE

Preferred Name

English

PHENOLPHTHALEIN

Official Name

English

PHENOLPHTHALEIN [HSDB]

Common Name

English

PHENPOLPHTHALEIN [VANDF]

Common Name

English

PHENOLPHTHALEIN [EP MONOGRAPH]

Common Name

English

NSC-10464

Code

English

PHENOLPHTHALEIN [MART.]

Common Name

English

PHENOLPHTHALEIN [IARC]

Common Name

English

PHENOLPHTHALEIN, WHITE

Common Name

English

3,3-BIS(P-HYDROXYPHENYL)PHTHALIDE

Common Name

English

PHENOLPHTHALEIN,WHITE [VANDF]

Common Name

English

Phenolphthalein [WHO-DD]

Common Name

English

1(3H)-ISOBENZOFURANONE, 3,3-BIS(4-HYDROXYPHENYL)-

Systematic Name

English

PHENOLPHTHALIN [MI]

Common Name

English

PHENOLPHTHALEIN [MI]

Common Name

English

PHENOLPHTHALEIN [VANDF]

Common Name

English

phenolphthalein [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A06AB04