SULFOBROMOPHTHALEIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H10Br4O10S2
Molecular Weight	794.033
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OHTXTCNTQJFRIG-UHFFFAOYSA-N

InChI=1S/C20H10Br4O10S2/c21-15-13-14(16(22)18(24)17(15)23)20(34-19(13)27,7-1-3-9(25)11(5-7)35(28,29)30)8-2-4-10(26)12(6-8)36(31,32)33/h1-6,25-26H,(H,28,29,30)(H,31,32,33)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9825739 | https://www.ncbi.nlm.nih.gov/pubmed/6072484 | https://www.ncbi.nlm.nih.gov/pubmed/772488 | https://www.ncbi.nlm.nih.gov/pubmed/14192521

Sulfobromophthalein (BSP) is a dye with a high affinity for organic anion transporting polypeptides (OATPs) and has been used as a substrate for multidrug resistance associated protein 2 (Mrp2). BSP is transported into hepatocytes by OATPs and, after conjugation to glutathione, is excreted into bile by Mrp2.3 It was found to inhibit the aldo-keto reductase ARK1C20. Sulfobromophthalein (BSP) is used in diagnosis of hepatic disorders.It is also used for the quantitative determination of proteins.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23920221 \| https://www.ncbi.nlm.nih.gov/pubmed/22394605	Substrate 661	44.0 nM [Ki]
glutathione S-transferase, Oesophagostomum dentatum 2 Target ID: glutathione S-transferase, Oesophagostomum dentatum Sources: https://www.ncbi.nlm.nih.gov/pubmed/18771610 \| https://www.ncbi.nlm.nih.gov/pubmed/21241694	Inhibitor 8504
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL2073676 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15618649	Inhibitor 8504	2.18 µM [Ki]
aldo-keto reductase family 1, member C20 2 Target ID: 116852.0 Gene Symbol: Akr1c20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16508162	Inhibitor 8504	1.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver disease 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6072484 https://www.ncbi.nlm.nih.gov/pubmed/772488 https://www.ncbi.nlm.nih.gov/pubmed/14192521 https://www.ncbi.nlm.nih.gov/pubmed/8903382	Diagnostic		Approved 8583	Bromosulfoftaleina Sodium Approved Use Diagnostic aid in hepatic function determination

AUC

Value	Dose	Co-administered	Analyte	Population
0.943 mg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19226651/	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFOBROMOPHTHALEIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1551.5 μg × min/mL EXPERIMENT https://koreascience.kr/article/JAKO199011919458798.pdf	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFOBROMOPHTHALEIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.07 min EXPERIMENT https://koreascience.kr/article/JAKO199011919458798.pdf	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		SULFOBROMOPHTHALEIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/	Disc. AE: Diaphoresis, Hypotension... AEs leading to discontinuation/dose reduction: Diaphoresis Hypotension Consciousness loss Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/

AEs

AE	Significance	Dose	Population
Consciousness loss	Disc. AE	5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/
Diaphoresis	Disc. AE	5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/
Hypotension	Disc. AE	5 mg/kg single, intravenous Recommended Dose: 5 mg/kg Route: intravenous Route: single Dose: 5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5319723/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP2B1 157 OATP1B3 961 MRP2 499 OAT3 747 NTCP 39 ASBT 7 OAT2 153 OAT4 150 OATP1B1 1079	OATP1A2 67 OATP1C1 2 NTCP 22

Drug as perpetrator

Target	Modality	Activity
OAT4 150	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	no [Inhibition 50 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [IC50 0.05 uM]
NTCP 40	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Mjg3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [IC50 7.3 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [Inhibition 0.52 uM]
OAT3 749	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjQxMzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [Inhibition 5 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [Inhibition 80 uM]
ASBT 8	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNzc4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [Ki 144 uM]
OAT2 155	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTU1NzExIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes
OATP2B1 162	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU3NDQzMSJ9fQ==	yes

Drug as victim

Target	Modality	Activity
OATP1A2 67	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIzIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes [Km 20 uM]
NTCP 22	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Mjg3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes
OATP1C1 2	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ1MzkwNCJ9fQ==	yes

PubMed

Title	Date	PubMed
Involvement of Mrp2 (Abcc2) in biliary excretion of moxifloxacin and its metabolites in the isolated perfused rat liver.	2008-01	18088505
Biliary excretion of flavopiridol and its glucuronides in the isolated perfused rat liver: role of multidrug resistance protein 2 (Mrp2).	2003-10-17	14511769

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 350mg/day, i.v.

Route of Administration: Intravenous

In Vitro Use Guide

In competitive binding studies in vitro between Sulfobromophthalein (BSP) and a series of organic anions (sodium fluorescein, indocyanine green, bilirubin, sodium taurocholate, flavaspidic acid glucaminate, and iodipamide methylglucamine), the incubation mixture contained 500 ug of BSP and equimolar amounts of the aforementional organic anions. On the average, 160 +/- 2 ug BSP was bound per mg of membrane protein and 1.4 +/-0.1 ug BSP bound per unit of Co++-CMPase activity in 15 membrane isolates. BSP binding was maximal at 500 ug BSP/ml in the incubation mix with proportionately less binding observed at lower concentrations. BSP concentrations above 500 ug/ml reduced BSP binding and produced dissolution of cell membranes.

Name

Type

Language

SULFOBROMOPHTHALEIN

Common Name

English

SULFOBROMPHTHALEIN

Preferred Name

English

SULFOBROMOPHTALEIN

Common Name

English

SULFOBROMOPHTHALEIN FREE ACID

Common Name

English

4,5,6,7-TETRABROMO-3',3''-DISULFOPHENOLPHTHALEIN

Common Name

English

BENZENESULFONIC ACID, 3,3'-(4,5,6,7-TETRABROMO-3-OXO-1(3H)-ISOBENZOFURANYLIDENE)BIS(6-HYDROXY-

Common Name

English

Sulfobromphthalein [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

V04CE02