PHENOLSULFONPHTHALEIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H14O5S
Molecular Weight	354.376
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(OS(=O)(=O)C3=CC=CC=C23)C4=CC=C(O)C=C4

InChI

InChIKey=BELBBZDIHDAJOR-UHFFFAOYSA-N

InChI=1S/C19H14O5S/c20-15-9-5-13(6-10-15)19(14-7-11-16(21)12-8-14)17-3-1-2-4-18(17)25(22,23)24-19/h1-12,20-21H

HIDE SMILES / InChI

Molecular Formula	C19H14O5S
Molecular Weight	354.376
Charge	0
Count

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

Description
Sources: https://www.drugs.com/mmx/psp.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15871747 and http://www.fci-ophthalmics.com/files/pdf/zone_quick_web.pdf

Phenolsulfonphthalein (Phenol red) is a pH indicator frequently used in cell biology laboratories. In medicine phenolsulfonphthalein is used as a test to help diagnose problems or disease of the kidneys. This test determines how well the kidneys are working. The test is based on the fact that phenol red is excreted almost entirely in the urine. Phenol red solution is administered intravenously, the urine produced is collected. By measuring the amount of phenol red excreted colorimetrically, kidney function can be determined. Phenolsulfonphthalein has being shown to be a mild estrogenic stimulus. Phenolsulfonphthalein as Phenol red thread test is used to diagnose dry eyes syndrome.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
oogenesis 1 Target ID: GO:0048477 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15871747	Activator 1447
amyloid fibril formation 8 Target ID: GO:1990000 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18457421	Inhibitor 8504		1.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dry eye syndrome 21 Sources: http://www.fci-ophthalmics.com/files/pdf/zone_quick_web.pdf	Diagnostic		Approved 8583	Phenol red thread test Approved Use Used to diagnose dry eyes syndrome
Kidney disease 6 Sources: https://www.drugs.com/cons/phenolsulfonphthalein-injection.html	Diagnostic		Approved 8583	PSP test Approved Use Renal function studies—PSP is indicated for evaluation of renal blood flow to aid in determination of renal function.

Doses

Dose	Population	Adverse events
1 mg/kg single, intravenous Studied dose Dose: 1 mg/kg Route: intravenous Route: single Dose: 1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/5911153/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5911153/	Sources: https://pubmed.ncbi.nlm.nih.gov/5911153/

PubMed

Title	Date	PubMed
Absorption of urea through the oral mucosa and estimation of the percentage of secreted whole saliva inadvertently swallowed during saliva collection.	2006-02	16023991
Simultaneous determination of naproxen, ketoprofen and phenol red in samples from rat intestinal permeability studies: HPLC method development and validation.	2005-09-15	15899568
The clearance of protein-bound solutes by hemofiltration and hemodiafiltration.	2005-08	16014068
Validated HPLC analytical method with programmed wavelength UV detection for simultaneous determination of DRF-4367 and Phenol red in rat in situ intestinal perfusion study.	2005-06-01	15907637
Antagonism of ATP responses at P2X receptor subtypes by the pH indicator dye, Phenol red.	2005-06	15778739
Oogenesis in cultures derived from adult human ovaries.	2005-05-05	15871747
Evaluation of the Schirmer and phenol red thread tests for measuring tear secretion in rabbits.	2005-04-09	15828747
Effect of red wine on the intestinal absorption of thiamine and folate in the rat: comparison with the effect of ethanol alone.	2005-04	15834233
Novel and established potassium channel openers stimulate hair growth in vitro: implications for their modes of action in hair follicles.	2005-04	15816824
A new tactic to treat postprandial hyperlipidemia in diabetic rats with gastroparesis by improving gastrointestinal transit.	2005-03-07	15740731
Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis.	2005-03	15743715
Characterization of secretory intestinal transport of phenolsulfonphthalein.	2005-02	15770077
Quantifying individual fruit fly consumption with Anastrepha suspensa (Diptera: Tephritidae).	2004-12	15666736
Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products.	2004-11-24	15548002
Inhibition of islet amyloid polypeptide fibril formation: a potential role for heteroaromatic interactions.	2004-11-16	15533050
Development of implant tablet for a week-long sustained release.	2004-11-05	15491811
Melatonin does not react rapidly with hydrogen peroxide.	2004-11	15621691
[Effect of glutamine on the non-steroidal anti-inflammatory drug-induced bacterial translocation].	2004-11	15564804
Absorption characteristics of compounds with different molecular weights after application to the unilateral kidney surface in rats.	2004-11	15451548
Ecdysone-induced accumulation of mosquito cells in the G1 phase of the cell cycle.	2004-09	15350503
A pH-sensitive assay for galactosyltransferase.	2004-07-15	15203327
Comparison of urinary excretion of phenolsulfonphthalein in an animal model for Wilson's disease (Long-Evans Cinnamon rats) with that in normal Wistar rats: involvement of primary active organic anion transporter.	2004-07-13	15367380
A comparison of tear volume (by tear meniscus height and phenol red thread test) and tear fluid osmolality measures in non-lens wearers and in contact lens wearers.	2004-07	15499232
Highly selective spectrophotometric flow-injection determination of trace amounts of bromide by catalytic effect on the oxidation of m-cresolsulfonephthalein by periodate.	2004-07	15248985
Increasing dialysate flow and dialyzer mass transfer area coefficient to increase the clearance of protein-bound solutes.	2004-07	15213283
Evaluation of lipid peroxidation in red blood cells by monitoring the uptake of sucrose and phenol red.	2004-06-24	15211617
[Influence of single leaf Asarum himalaicum on renal function of rabbits].	2004-05	15339444
Absorption of phenolsulfonphthalein as a model across the mesenteric surface in rats to determine the drug absorption route after intraperitoneal administration.	2004-05	15142348
Comparison of the disposition behavior of organic anions in an animal model for Wilson's disease (Long-Evans Cinnamon rats) with that in normal Long-Evans Agouti rats.	2004-04	15499181
Pharmacokinetics of phenol red in rat models of liver damage prepared by liver targeting of carbon tetrachloride.	2004-04	15056875
Ion transport across model lipid membranes containing light-harvesting complex II: an effect of light.	2004-03-19	15043842
Proton uptake upon anaerobic reduction of the Paracoccus denitrificans cytochrome c oxidase: a kinetic investigation of the K354M and D124N mutants.	2004-03-16	15005632
[Studies on antitussive, antiasthmatic and expectorant action of chenodeoxycholine acid].	2004-03	15272787
Effects of culture conditions on taurine uptake by various variants of human endometrial carcinoma cells in culture.	2004-03	15042449
Drinking 300 mL of clear fluid two hours before surgery has no effect on gastric fluid volume and pH in fasting and non-fasting obese patients.	2004-02	14766684
Expression levels of renal organic anion transporters (OATs) and their correlation with anionic drug excretion in patients with renal diseases.	2004-01	14984259
Segmental difference in epithelial and mucosal barrier functions between the jejunum and the ileum in cold storage small bowel grafts in the rat.	2004	15150898
Interexaminer difference and the effect of training on the phenol red thread test results in Hong Kong-Chinese.	2003-12	14688545
Differences in clinical parameters and tear film of tolerant and intolerant contact lens wearers.	2003-12	14638706
The relation between tear film tests in patients with dry eye disease.	2003-11	14622360
Role of bile in intestinal barrier function and its inhibitory effect on bacterial translocation in obstructive jaundice in rats.	2003-11	14572768
The effects of lectins on indomethacin-induced small intestinal ulceration.	2003-10	14690482
Sildenafil, a phosphodiesterase-5 inhibitor, delays gastric emptying and gastrointestinal transit of liquid in awake rats.	2003-10	14627356
Major role of organic anion transporters in the uptake of phenolsulfonphthalein in the kidney.	2003-08-15	12954363
Effects of phenol red on CFU-f differentiation and formation.	2003-08	14565599
[The reactions between acidic phenolsulfonphthaleins and human serum albumin].	2003-06	12953536
[Study on extraction separation of Bi(III), Fe(III), Cu(II), Ni(II), Co(II) and Pb(II) in PEG-(NH4)2SO4-PR system using spectrophotometry].	2003-04	12961891
[The high-sensitivity determination of protein concentration by the enhancement of resonance light scattering of chlorophenol red].	2003-04	12961856
Mechanism of active secretion of phenolsulfonphthalein in the liver via Mrp2 (abcc2), an organic anion transporter.	2003	15618741
Spraying of phenol red dye as a screening test for Helicobacter pylori infection in surgically resected stomach specimens.	2003	14673721

Patents

Sample Use Guides

In Vivo Use Guide

Usual adult and adolescent dose Renal function studies and Residual bladder urine determinations Intravenous (rapid) or intramuscular, 6 mg. Test procedure: Empty bladder; receive injection; empty bladder again

Route of Administration: Intravenous

In Vitro Use Guide

Phenolsulfonphthalein at 10 mM inhibited hIAPP core amyloidogenic peptides aggregation

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:53 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:53 GMT 2025`
Record UNII	I6G9Y0J1OJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENOLSULFONPHTHALEIN

Official Name

English

NSC-10459

Preferred Name

English

PHENOLSULFONPHTHALEIN [MI]

Common Name

English

PHENOLSULFONPHTHALEIN [EP MONOGRAPH]

Common Name

English

PHENOL, 4,4'-(3H-2,1-BENZOXATHIOL-3-YLIDENE)BIS-, (S,S-DIOXIDE)

Common Name

English

Phenolsulfonphthalein [WHO-DD]

Common Name

English

PHENOLSULFONPHTHALEIN [MART.]

Common Name

English

3,3-BIS(4-HYDROXYPHENYL)-3H-2,1-BENZOXATHIOLE 1,1-DIOXIDE

Systematic Name

English

PHENOLSULFONPHTHALEIN [JAN]

Common Name

English

PHENOL RED

Common Name

English

PHENOLSULFONPHTHALEIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

V04CH03