Page last updated: 2024-12-05

sulfobromophthalein

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Sulfobromophthalein (BSP) is a dye that has been used clinically for over 70 years as a liver function test. It is a water-soluble, non-toxic dye that is excreted by the liver. When injected intravenously, BSP is rapidly removed from the bloodstream and concentrated in the liver. The rate at which BSP is removed from the blood is a measure of liver function. BSP is synthesized by reacting phthalic anhydride with bromine and sulfuric acid. It is an important diagnostic tool for liver disease. The dye is studied to assess liver function, evaluate the efficacy of new drugs, and monitor the progression of liver disease.'
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Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5345
CHEMBL ID574431
CHEBI ID63836
SCHEMBL ID743910
MeSH IDM0020785

Synonyms (33)

Synonym
297-83-6
sulfobromophthalein
NCGC00159391-02
sulphobromophthalein (ban)
D08548
sulphobromophthalein
sulfobromophtalein
CHEMBL574431 ,
chebi:63836 ,
sulfobromphthalein
sulfobromophthalein free acid
bdbm50300126
2-hydroxy-5-[4,5,6,7-tetrabromo-1-(4-hydroxy-3-sulfophenyl)-3-oxo-2-benzofuran-1-yl]benzenesulfonic acid
NCGC00159391-03
0c2p5qkl36 ,
3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)bis(6-hydroxybenzenesulphonic) acid
sulphobromophthalein [ban]
einecs 206-047-5
unii-0c2p5qkl36
benzenesulfonic acid, 3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)bis(6-hydroxy-
4,5,6,7-tetrabromo-3',3''-disulfophenolphthalein
3,3'-(4,5,6,7-tetrabromo-3-oxo-1,3-dihydro-2-benzofuran-1,1-diyl)bis(6-hydroxybenzenesulfonic acid)
sulfobromphthalein [who-dd]
SCHEMBL743910
AKOS024387382
DTXSID4075378
3,3'-(tetrabromophthalidylidene)bis[6-hydroxybenzenesulfonic acid]
SR-01000944702-1
sr-01000944702
3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)-bis[6-hydroxy-benzenesulfonic acid]
DB13215
Q27132840
5,5'-(4,5,6,7-tetrabromo-3-oxo-1,3-dihydroisobenzofuran-1,1-diyl)bis(2-hydroxybenzenesulfonic acid)

Research Excerpts

Effects

ExcerptReferenceRelevance
"sulfobromophthalein complex has been found to be 4."( Isolation of a sulfobromophthalein-binding protein from hepatocyte plasma membrane.
Gazzin, B; Liut, G; Luciani, M; Lunazzi, G; Panfili, E; Sandri, G; Sottocasa, G; Tiribelli, C, 1978
)
1.33

Treatment

ExcerptReferenceRelevance
"In sulfobromophthalein-treated animals, urine excretion increases were only to 0.5 and 3.0% for I and II, respectively."( Comparison of 99mTc-N-pyridoxyl-5-methyltryptophan and 99mTc-N-(3-bromo-2,4,6-trimethylacetanilide)-iminodiace tate as hepatobiliary radiopharmaceuticals in rats.
Bloedow, DC; Eshima, D; Fritzberg, AR; Johnson, DL, 1984
)
0.78

Toxicity

ExcerptReferenceRelevance
" The same total dose administered at daily rates of 50 or 200 micrograms/kg was more toxic and killed all sheep."( The toxicity of phomopsin for sheep.
Jago, MV; Payne, AL; Peterson, JE; Stewart, PL, 1987
)
0.27
"An animal model for the identification and definition of toxic liver damage, based on the investigation of the BSP metabolism in the rat is proposed."( Bromsulphalein (BSP) kinetics in the rat: a new approach in evaluating experimental hepatotoxicity.
Biondi, AM; Cavanna, A; Macrì, G; Molino, G; Ugazio, G; Urigu, S, 1982
)
0.26
"Administration of the non-metabolizable organic anion indocyanine green (ICG) prior to a toxic dose of acetaminophen (4-acetamidophenol; APAP) reduces liver injury 24h after dosing."( Cholestasis induced by model organic anions protects from acetaminophen hepatotoxicity in male CD-1 mice.
Hennig, GE; Manautou, JE; Silva, VM, 2006
)
0.33

Pharmacokinetics

ExcerptReferenceRelevance
" A quantitative description of liver function in terms of regional distribution and elimination rate constants will require either a pharmacokinetic model that expressly includes the effects of bilirubin, the development of new anionic hepatobiliary agents capable of displacing endogenous bilirubin from transport binding sites, or the development of new hepatobiliary agents that use a different clearance mechanism from that used by bilirubin."( Hepatic clearance mechanism of Tc-99m-HIDA and its effect on quantitation of hepatobiliary function: Concise communication.
Cooper, M; Faith, W; Harvey, E; Loberg, M; Ryan, J; Sikorski, S, 1979
)
0.26
" Such pharmacokinetic behavior appeared to be related to the contractive effect of morphine on the bile duct, and naloxone facilitated the excretion of morphine via this route."( Naloxone affects both pharmacokinetics and pharmacodynamics of morphine. Application of direct correlation analysis.
Ishikawa, K; Kogure, M; Kubo, T; Shibanoki, S, 1991
)
0.28
" Pharmacokinetic analysis of the plasma elimination curve permitted the calculation of clearance, constants k1 and k2, and the retention percentage at 45 min."( Indocyanine green-sulfobromophthalein pharmacokinetics for diagnosing primary biliary cirrhosis and assessing histological severity.
Chazouillères, O; Giboudeau, J; Gufflet, V; Poupon, R; Vaubourdolle, M, 1991
)
0.62
" A pharmacokinetic study of the results was performed following a multicompartmental model with 7 transfer constants to describe the physiological disposition of the dye."( Pharmacokinetics, hepatic biotransformation and biliary and urinary excretion of bromosulfophthalein (BSP) in an experimental liver disease mimicking biliary cirrhosis.
Esteller, A; Fernandez-Lastra, C; Gomez-Bautista, M; Jimenez, R; Mariño, EL; Torres, MD,
)
0.13
" Paracetamol, the only metabolised drug which is conjugated for which pharmacokinetic parameters have been accurately determined in obesity, undergoes increased clearance in obese subjects."( Pharmacokinetics of drugs in obesity.
Abernethy, DR; Greenblatt, DJ,
)
0.13
"022 is a novel recombinant, unglycosylated plasminogen activator comprising only the kringle 2 and protease domains of human tissue-type plasminogen activator (t-PA), and it has a longer half-life than t-PA."( Influence of hepatic and renal failure on pharmacokinetic properties of the novel recombinant plasminogen activator BM 06.022 in rats.
Martin, U; Sponer, G; Strein, K,
)
0.13
"This study contains a pharmacokinetic analysis on the efflux of organic anions from the liver into the bloodstream (sinusoidal efflux) with specific reference to the influence of albumin."( Pharmacokinetic modeling of the sinusoidal efflux of anionic ligands from the isolated perfused rat liver: the influence of albumin.
Groothuis, GM; Meijer, DK; Nijssen, HM; Proost, JH; Strating, CB, 1993
)
0.29
"A physiologically based pharmacokinetic model was established to describe the hepatobiliary excretion process for ligands which are excreted into the bile without metabolic conversion."( Construction of a physiologically based pharmacokinetic model to describe the hepatobiliary excretion process of ligands: quantitative estimation of intracellular diffusion.
Hanano, M; Sathirakul, K; Sugiyama, Y; Suzuki, H; Yasuda, K, 1993
)
0.29
" Estimates of pharmacokinetic variables were compared among the 4 exercise intensities, using a Friedman repeated-measures analysis on ranks and linear regression."( Intensity-dependent effects of acute submaximal exercise on the pharmacokinetics of bromsulphalein in horses.
Dyke, TM; Hinchcliff, KW; Sams, RA, 1998
)
0.3
" Elimination half-life of BSP increased significantly with increasing exercise intensity and was linearly related to exercise intensity."( Intensity-dependent effects of acute submaximal exercise on the pharmacokinetics of bromsulphalein in horses.
Dyke, TM; Hinchcliff, KW; Sams, RA, 1998
)
0.3
" The aims of this study were to elucidate its pharmacokinetic characteristics, tissue distribution, plasma protein binding and excretion properties and underlying mechanisms of deuxemether in rats based on the simultaneous determination of MHD and DMD."( Pharmacokinetics, tissue distribution and excretion of a new photodynamic drug deuxemether.
Hao, H; He, H; Li, X; Wang, G; Wang, R; Wang, W; Xie, H; Xu, M, 2008
)
0.35
" Previous reports indicate that ELT is mainly eliminated in the liver, although its pharmacokinetic profile has not yet been clarified in detail."( Pharmacokinetics and hepatic uptake of eltrombopag, a novel platelet-increasing agent.
Horikawa, M; Ishiwata, N; Kato, Y; Matsubara, K; Nakamichi, N; Silver, DL; Sugiura, T; Takeuchi, K; Umeda, S, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
" These parameters were compared with literature and in vivo experimental values, and the results suggest that the model should be suitable for the study of metabolic drug-drug interactions occurring in the rat liver."( An assessment of the suitability of a modified technique of in situ rat-liver perfusion for the study of certain hepatic drug-drug interactions.
Fairweather, I; Maguire, TA; Swanton, JG; Temple, DJ, 1984
)
0.27

Bioavailability

ExcerptReferenceRelevance
" A kinetic model study on the transfer constants between various body compartments has indicated that rifampicin is rapidly absorbed from the intestine and that the absorption rate increases with time."( Clinical pharmacokinetics of rifampicin.
Acocella, G,
)
0.13
" The amphiphilic compound exhibits virtually no systemic bioavailability despite proteolytic stability and proven enteral absorption."( First-pass elimination of a peptidomimetic thrombin inhibitor is due to carrier-mediated uptake by the liver. Interaction with bile acid transport systems.
Dickneite, G; Eckhardt, U; Petzinger, E; Reers, M; Stüber, W, 1996
)
0.29
" In continuation of the tests investigating the factors limiting bioavailability of boswellic acids, the present study examined the permeability of KBA and AKBA in human Caco-2 cell lines."( Permeation of Boswellia extract in the Caco-2 model and possible interactions of its constituents KBA and AKBA with OATP1B3 and MRP2.
Abdel-Tawab, M; Fricker, G; Hummel, J; Kanzer, J; Krüger, P; Schubert-Zsilavecz, M, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" The other cholestatic reaction is dependent on dosage and type of preparation and can develop in any OC user."( [Oral contraceptives and the liver].
Brandt, KH; Bronkhorst, FB; de Pagter, AG; van Berge Henegouwen, GP, 1979
)
0.26
" Repeated dosing with tilorone produced a dose-dependent increase in hepatic concentration of unchanged and metabolized tilorone."( Effect of tilorone hydrochloride on hepatic disposition of sulphobromophthalein (BSP) in the rat.
Hoenig, V; Werner, F, 1978
)
0.26
" These permit the elaboration of dose-response lines for the substances in question, the calculation of median effective doses and the statistical analysis of differences in liver-damaging potency."( Quantitative aspects in the assessment of liver injury.
Plaa, GL, 1976
)
0.26
" A tendency for slower elimination of BSP at 10 mg kg-1 suggested saturation of excretory mechanisms, while at 2 mg kg-1 accurate dosing and assay of low BSP concentrations were difficult."( Bromsulphthalein and indocyanine green elimination from plasma, and urinary bromsulphthalein excretion, in normal cats.
Middleton, DJ; Watson, AD, 1989
)
0.28
") or repeated clonidine dosing (0."( Clonidine effects on disposition of xenobiotics in rats: inhibited elimination of flow-limited but not extraction-limited agents.
Ben-Zvi, Z; Hurwitz, A, 1988
)
0.27
" Chronic dosing with morphine or clonidine caused partial tolerance and cross-tolerance to the rise in hepatic BSP caused by an acute challenge with either agonist."( Tolerance to effects of clonidine and morphine on sulfobromophthalein disposition in mice.
Ben-Zvi, Z; Graham, CE; Hurwitz, A, 1987
)
0.53
" The log dose-response curve for E217G-induced cholestasis was much steeper and was shifted to the right in the presence of a 60 mumol/hr infusion of taurocholate."( Taurocholate and steroid glucuronides: mutual protection against cholestasis in the isolated perfused rat liver.
Durham, S; Vore, M, 1986
)
0.27
"A significant dose-response correlation was found between taurolithocholate and the degree of cholestasis."( Cholestasis induced by sodium taurolithocholate in isolated hamster liver.
King, JE; Schoenfield, LJ, 1971
)
0.25
" However, tissue concentrations of Adr were generally lower in rats treated ip with Adr or Adr/L than in animals dosed iv."( Effect of route administration and liposome entrapment on the metabolism and disposition of adriamycin in the rat.
Parker, RJ; Priester, ER; Sieber, SM,
)
0.13
" Each animal was dosed 30 min."( Effects of quinuronium sulfate pre-exposure on hepatic excretion of sulfobromophthalein (BSP) as measured by isolated perfused rat liver.
Frøslie, A; Mitema, ES; Nafstad, I, 1983
)
0.5
" Furthermore, the results of repetitive dosing may also be simulated."( Physiological flow model for drug elimination interactions in the rat.
Luecke, RH; Thomason, LE; Wosilait, WD, 1980
)
0.26
" Additional dose-response studies of biliary permeability to [14C]sucrose, using sulfobromophthalein and rose bengal, showed that this effect was dose-dependent and rapidly reversed by interruption of dye administration."( Effect of cholephilic dyes on hepatic tight junctional permeability in the rat.
Crocenzi, FA; Marinelli, RA; Rodríguez Garay, EA; Roma, MG, 1995
)
0.52
" Dose-response curves were analysed by a four-parameter sigmoid curve-fitting program to determine competitor potency."( Drug competition for intracellular triiodothyronine-binding sites.
Barlow, JW; Curtis, AJ; Loidl, NM; Raggatt, LE; Stockigt, JR; Topliss, DJ, 1994
)
0.29
" In these studies, overnight fasted male CD-1 mice were dosed (i."( Cholestasis induced by model organic anions protects from acetaminophen hepatotoxicity in male CD-1 mice.
Hennig, GE; Manautou, JE; Silva, VM, 2006
)
0.33
"The objective of this study was to determine whether the rabbit was a suitable model to test new synthetic androgens for potential liver toxicity within a short dosing interval."( Effects of synthetic androgens on liver function using the rabbit as a model.
Attardi, BJ; Hild, SA; Koduri, S; Reel, JR; Till, BA,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
dyenull
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
2-benzofurans
organobromine compoundA compound containing at least one carbon-bromine bond.
organosulfonic acidAn organic derivative of sulfonic acid in which the sulfo group is linked directly to carbon.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency15.81140.140911.194039.8107AID2451
LuciferasePhotinus pyralis (common eastern firefly)Potency28.69540.007215.758889.3584AID624030
USP1 protein, partialHomo sapiens (human)Potency50.11870.031637.5844354.8130AID504865
GLS proteinHomo sapiens (human)Potency11.22020.35487.935539.8107AID624170
Microtubule-associated protein tauHomo sapiens (human)Potency35.48130.180013.557439.8107AID1460
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency89.12510.010323.856763.0957AID2662
DNA polymerase kappa isoform 1Homo sapiens (human)Potency28.18380.031622.3146100.0000AID588579
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency28.18380.251215.843239.8107AID504327
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency35.48130.060110.745337.9330AID492961
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hematopoietic prostaglandin D synthaseHomo sapiens (human)IC50 (µMol)27.00000.07100.92223.8000AID442514
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processHematopoietic prostaglandin D synthaseHomo sapiens (human)
prostaglandin metabolic processHematopoietic prostaglandin D synthaseHomo sapiens (human)
signal transductionHematopoietic prostaglandin D synthaseHomo sapiens (human)
locomotory behaviorHematopoietic prostaglandin D synthaseHomo sapiens (human)
negative regulation of male germ cell proliferationHematopoietic prostaglandin D synthaseHomo sapiens (human)
glutathione metabolic processHematopoietic prostaglandin D synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
magnesium ion bindingHematopoietic prostaglandin D synthaseHomo sapiens (human)
glutathione transferase activityHematopoietic prostaglandin D synthaseHomo sapiens (human)
prostaglandin-D synthase activityHematopoietic prostaglandin D synthaseHomo sapiens (human)
calcium ion bindingHematopoietic prostaglandin D synthaseHomo sapiens (human)
protein bindingHematopoietic prostaglandin D synthaseHomo sapiens (human)
protein homodimerization activityHematopoietic prostaglandin D synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmHematopoietic prostaglandin D synthaseHomo sapiens (human)
cytoplasmHematopoietic prostaglandin D synthaseHomo sapiens (human)
cytosolHematopoietic prostaglandin D synthaseHomo sapiens (human)
intracellular membrane-bounded organelleHematopoietic prostaglandin D synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID442514Inhibition of human H-PGDS expressed in Escherichia coli BL21 assessed as rate of glutathione-chloro-dinitro benzene conjugation2010European journal of medicinal chemistry, Feb, Volume: 45, Issue:2
Identification and characterisation of new inhibitors for the human hematopoietic prostaglandin D2 synthase.
AID1217112Inhibition of OATP1B1-mediated [3H]estrone-3-sulfate uptake in human OATP1B1 expressing HEK293/PDZK1 cells by scintillation counting2011Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6
Pharmacokinetics and hepatic uptake of eltrombopag, a novel platelet-increasing agent.
AID681235TP_TRANSPORTER: inhibition of thyroxine uptake (thyroxine:10nM, bromosul-fophthalein: 100 uM) in Xenopus laevis oocytes2003The Journal of biological chemistry, Oct-10, Volume: 278, Issue:41
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1217062Inhibition of OATP1B3-mediated [3H]estradiol 17beta-glucuronide uptake in human OATP1B3 expressing HEK293/PDZK1 cells by scintillation counting2011Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6
Pharmacokinetics and hepatic uptake of eltrombopag, a novel platelet-increasing agent.
AID681244TP_TRANSPORTER: inhibition of 3,3',5-triiodothyronine uptake (3,3',5-triiodothyronine:10nM, bromosul-fophthalein: 100 uM) in Xenopus laevis oocytes2003The Journal of biological chemistry, Oct-10, Volume: 278, Issue:41
Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.
AID1217113Inhibition of OATP2B1-mediated [3H]estrone-3-sulfate uptake in human OATP2B1 expressing HEK293/PDZK1 cells by scintillation counting2011Drug metabolism and disposition: the biological fate of chemicals, Jun, Volume: 39, Issue:6
Pharmacokinetics and hepatic uptake of eltrombopag, a novel platelet-increasing agent.
AID588210Human drug-induced liver injury (DILI) modelling dataset from Ekins et al2010Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 38, Issue:12
A predictive ligand-based Bayesian model for human drug-induced liver injury.
AID442515Inhibition of human H-PGDS expressed in Escherichia coli BL21 assessed as rate of glutathione-chloro-dinitro benzene conjugation at 50 uM2010European journal of medicinal chemistry, Feb, Volume: 45, Issue:2
Identification and characterisation of new inhibitors for the human hematopoietic prostaglandin D2 synthase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (2,979)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902588 (86.87)18.7374
1990's230 (7.72)18.2507
2000's103 (3.46)29.6817
2010's52 (1.75)24.3611
2020's6 (0.20)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.51 (24.57)
Research Supply Index8.08 (2.92)
Research Growth Index4.06 (4.65)
Search Engine Demand Index41.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials33 (1.03%)5.53%
Reviews87 (2.71%)6.00%
Case Studies59 (1.84%)4.05%
Observational0 (0.00%)0.25%
Other3,030 (94.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]