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Details

Stereochemistry ACHIRAL
Molecular Formula C20H8Br4O10S2.2Na
Molecular Weight 837.9981
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFOBROMOPHTHALEIN SODIUM

SMILES

c1cc(c(cc1C(=C2C=CC(=O)C(=C2)S(=O)(=O)O)c3c(c(c(c(c3Br)Br)Br)Br)C(=O)[O-])S(=O)(=O)O)[O-].[Na+].[Na+]

InChI

InChIKey=HXUITPQMHVLBNV-LIYVDSPJSA-L
InChI=1S/C20H10Br4O10S2.2Na/c21-16-14(15(20(27)28)17(22)19(24)18(16)23)13(7-1-3-9(25)11(5-7)35(29,30)31)8-2-4-10(26)12(6-8)36(32,33)34;;/h1-6,25H,(H,27,28)(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/b13-8+;;

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H8Br4O10S2
Molecular Weight 792.0186
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: Sulfobromophthalein sodium (BSP, Bromsulphalein) has been used extensively for testing hepatic function since its introduction by Rosenthal and White in 1925

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Bromosulfoftaleina Sodium

Approved Use

Diagnostic aid in hepatic function determination
PubMed

PubMed

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

Sample Use Guides

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 Sat Jun 26 11:28:56 UTC 2021
Edited
by admin
on Sat Jun 26 11:28:56 UTC 2021
Record UNII
62E5JU30OV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFOBROMOPHTHALEIN SODIUM
HSDB   MART.   MI  
Common Name English
SULFOBROMOPTHALEIN SODIUM
Common Name English
SULFOBROMOPHTHALEIN SODIUM [JAN]
Common Name English
4,5,6,7-TETRABROMO-3',3''-DISULFOPHENOLPHTHALEIN DISODIUM SALT
Common Name English
HEPARTEST
Brand Name English
SULFOBROMPHTHALEIN SODIUM
WHO-DD  
Common Name English
BSP SODIUM
Common Name English
SODIUM BROMSULPHTHALEIN
Common Name English
SULFOBROMPHTHALEIN SODIUM [WHO-DD]
Common Name English
BROMSULPHTHALEIN
Common Name English
SULFOBROMOPHTHALEIN SODIUM [MART.]
Common Name English
HEPATOSULFALEIN
Brand Name English
BENZENESULFONIC ACID, 3,3'-(4,5,6,7-TETRABROMO-3-OXO-1(3H)-ISOBENZOFURANYLIDENE)BIS(6-HYDROXY-, DISODIUM SALT
Common Name English
HEPATESTABROME
Brand Name English
SULFOBROMOPHTHALEIN SODIUM [HSDB]
Common Name English
SULFOBROMOPHTHALEIN SODIUM [MI]
Common Name English
PHENOLPHTHALEIN, 4,5,6,7-TETRABROMO-3',3''-DISULFO-, DISODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C461
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
Code System Code Type Description
FDA UNII
62E5JU30OV
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
CAS
1260372-63-1
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
ALTERNATIVE
NCI_THESAURUS
C87725
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-761-0
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
CAS
71-67-0
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
WIKIPEDIA
Sulphobromophthalein
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL574431
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
EPA CompTox
71-67-0
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
HSDB
2183
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
EVMPD
SUB15430MIG
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
RXCUI
203200
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M10354
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY Merck Index
PUBCHEM
44134957
Created by admin on Sat Jun 26 11:28:57 UTC 2021 , Edited by admin on Sat Jun 26 11:28:57 UTC 2021
PRIMARY
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