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=CC=C(C=C1S(O)(=O)=O)C2(OC(=O)C3=C(Br)C(Br)=C(Br)C(Br)=C23)C4=CC(=C(O)C=C4)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

Molecular Formula	C20H10Br4O10S2
Molecular Weight	794.033
Charge	0
Count

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

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 8297
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL2073676 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15618649	Inhibitor 8297	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 8297	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 8429	Bromosulfoftaleina Sodium Approved Use Diagnostic aid in hepatic function determination

PubMed

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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:43:53 UTC 2023` Edited by `admin` on `Fri Dec 15 16:43:53 UTC 2023`
Record UNII	0C2P5QKL36
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFOBROMOPHTHALEIN

Common Name

English

SULFOBROMOPHTALEIN

Common Name

English

SULFOBROMOPHTHALEIN FREE ACID

Common Name

English

SULFOBROMPHTHALEIN

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