A synthetic dye called sulfobromophthalein disodium salt was first presented in 1925 as a therapeutic tool for evaluating liver function[1]. The pH indicator dye sulfobromophthalein (BSP) exhibits rapid (17 s, proton-dependent quinoidal-phenolic tautomerism, pK = 8.5) [1]. Organic anionic transporting polypeptide 1B1 (OATP1B1), OATP1B3, OATP1A2, and OATP2B1, as well as multidrug resistance protein 2 (MDR2), have all been shown to be both substrates and inhibitors of bromosulfalein [2].

Absorption, Distribution and Excretion
WHEN HEPATIC FUNCTION IS SEVERELY IMPAIRED, UP TO 10-25%...MAY BE EXCRETED IN URINE. NORMALLY...LESS THAN 2% OF DOSE IS EXCRETED IN THIS WAY, & EXTRAHEPATIC REMOVAL OF SULFOBROMOPTHALEIN CAN BE DISREGARDED.
NORMAL METABOLISM & EXCRETION OF SULFOBROMOPHTHALEIN DEPEND ON HEPATIC BLOOD FLOW, ABILITY OF LIVER CELLS TO TAKE UP & CONCN THE DYE, & INTAKE BILIARY EXCRETION.
...METABOLIZED IN LIVER BY CONJUGATION WITH GLUTATHIONE, & BOTH FREE & CONJUGATED...ARE EXCRETED INTO BILE. ... DYE DOES NOT UNDERGO ENTEROHEPATIC CIRCULATION...& IS EXCRETED PRIMARILY IN FECES. ... EXCRETION OF DYE IS USUALLY COMPLETE WITHIN 24 HR.
FOLLOWING IV ADMIN...ALMOST COMPLETELY BOUND TO PLASMA PROTEINS IN BLOOD, MAINLY ALBUMIN & ALPHA1 LIPOPROTEINS. DYE IS RAPIDLY TAKEN UP & BRIEFLY STORED BY HEPATIC PARENCHYMAL CELLS. ... SMALL AMT...MAY BE TAKEN UP BY SKELETAL MUSCLE, BUT EXTRA-HEPATIC TISSUE UPTAKE IS MINIMAL. ...DOES NOT CROSS PLACENTA.
For more Absorption, Distribution and Excretion (Complete) data for SODIUM SULFOBROMOPHTHALEIN (6 total), please visit the HSDB record page.

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Metabolism / Metabolites
S-ARYLTRANSFERASE IS THOUGHT TO BE INVOLVED IN METABOLISM OF SULFOBROMOPHTHALEIN...
IT IS EXCRETED IN BILE OF RATS AS BSP-GLUTATHIONE & OTHER AMINOACYL CONJUGATES, FORMED BY CONDENSATION OF BSP WITH GLUTATHIONE, PROBABLY WITHOUT ELIMINATION OF ANY OF BROMINE ATOMS.
SULFOBROMOPHTHALEIN /WAS METABOLIZED TO THE FOLLOWING/ S-(3,3-BIS(4-HYDROXY-3-SULFOPHENYL) TRIBROMOPHTHALIDYL)GLUTATHIONE IN DOG; JAVITT NB, ET AL, J CLIN INVEST, 39, 1570 (1960). SULFOBROMOPHTHALEIN-BETA-D-GLUCURONIDE IN LIVER; HIRAYAMA C, ET AL, SAISHIN IGAKU, 17, 2520 (1962).

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Biological Half-Life
IN ONE STUDY IN SMALL NUMBER OF NORMAL SUBJECTS, PLASMA HALF-LIFE AVG ABOUT 4 MIN. LIVER HAS STORAGE CAPACITY...WHICH IS PROPORTIONAL TO PLASMA CONCN OF DYE, & RANGES FROM 50-75 MG OF SULFOBROMOPHTHALEIN...PER MG OF DYE PER 100 ML OF PLASMA IN PT WITH NORMAL LIVER FUNCTION.

Interactions
DEHYDROCHOLIC ACID, CHLORTETRACYCLINE, SULFONAMIDES, NOVOBIOCIN, & MONOAMINE OXIDASE INHIBITORS MAY ALSO INCR SULFOBROMOPHTHALEIN RETENTION, ALTHOUGH POSSIBILITY OF ACTUAL LIVER DAMAGE SHOULD BE CONSIDERED IN PT RECEIVING CHLORTETRACYCLINE, SULFONAMIDES, OR NOVOBIOCIN.
SIMULTANEOUS ADMIN OF INDOCYANINE GREEN...MAY RESULT IN IMPAIRMENT OF HEPATIC EXCRETION...
CHOLECYSTOGRAPHIC AGENTS...REPORTED TO COMPETITIVELY INTERFERE WITH SULFOBROMOPHTHALEIN CLEARANCE & EXCRETION... ETHOXAZENE, PHENAZOPYRIDINE, PHENOLPHTHALEIN, & PHENOLSULFONPHTHALEIN (PSP) MAY PRODUCE APPARENT DECR EXCRETION OF SULFOBROMOPHTHALEIN BY INTERFERING WITH COLORIMETRIC MEASUREMENT...
BILIARY EXCRETION RATE & RATE OF PLASMA DISAPPEARANCE OF SULFOBROMOPHTHALEIN... WERE SHOWN...TO INCR AFTER PRE-TREATMENT WITH PHENOBARBITAL & OTHER MICROSOMAL-ENZYME INDUCERS IN RATS, & INCR EXCRETION CORRELATED WELL WITH INCR IN BILE FLOW RATES.
For more Interactions (Complete) data for SODIUM SULFOBROMOPHTHALEIN (7 total), please visit the HSDB record page.

[1]. Substrate-dependent inhibition of organic anion transporting polypeptide 1B1: comparative analysis with prototypical probe substrates estradiol-17β-glucuronide, estrone-3-sulfate, and sulfobromophthalein. Drug Metab Dispos. 2013 Oct;41(10):1859-66.

Bromosulfophthalein sodium is an organic sodium salt that is the disodium salt of bromosulfophthalein. It has a role as a dye. It contains a bromosulfophthalein(2-). It is functionally related to a 2-benzofuran-1(3H)-one.
A phenolphthalein that is used as a diagnostic aid in hepatic function determination.

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Mechanism of Action
SULFOBROMOPHTHALEIN TEST FOR LIVER FUNCTION IS BASED ON THE FACT THAT IN PT WITH HEPATIC DYSFUNCTION, PERCENTAGE DISAPPEARANCE RATE & EST STORAGE CAPACITY...ARE DECR & PLASMA HALF-LIFE & EST EXCRETORY TIME OF DYE ARE INCR.

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Therapeutic Uses
Indicators and Reagents; Phthalein Dyes
FORTY-FIVE MIN AFTER INJECTION...4-5 ML OF BLOOD IS WITHDRAWN FROM OPPOSITE ARM TO AVOID CONTAMINATION OF SAMPLE. ...SOME CLINICIANS TAKE SINGLE SAMPLE @ 30 MIN & OTHERS @ 60 MIN. AMT OF DYE RETAINED IN THE SERUM IS DETERMINED COLORIMETRICALLY.
USE...IN HEPATIC FUNCTION DETERMINATION IS NOT BASED ON ITS PHARMACOLOGIC EFFECTS BUT ON ITS DISTRIBUTION, METABOLISM, & EXCRETION FROM BODY.
...HELPFUL IN DETECTING HEPATIC DAMAGE IN PT WHO HAVE BEEN EXPOSED TO HEPATOTOXINS & IN RECOGNIZING METASTATIC CARCINOMA. ...ALSO BEEN USED TO DISTINGUISH UPPER GI HEMORRHAGE DUE TO PEPTIC ULCER FROM THAT DUE TO ESOPHAGEAL VARICES & FOR DIAGNOSIS OF DUBIN-JOHNSON OR ROTOR SYNDROMES. ...USED TO EST HEPATIC BLOOD FLOW...
For more Therapeutic Uses (Complete) data for SODIUM SULFOBROMOPHTHALEIN (8 total), please visit the HSDB record page.

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Drug Warnings
HIGH BLOOD LEVELS OF BILIRUBIN MAY INTERFERE WITH MEASUREMENT OF SULFOBROMOPHTHALEIN... HEPARIN...INCR COLOR INTENSITY...IN SERUM & CAUSES SHIFT IN ABSORPTION... ... SULFOBROMOPHTHALEIN MAY PRODUCE...INCR IN OTHER LABORATORY TEST RESULTS...SERUM CALCIUM, SERUM CREATINE & CREATININE, UROBILINOGEN, BLOOD PROTEIN...
PARENTERAL CHOLECYSTOGRAPHIC AGENTS ARE SATURATED SOLN, & PT ALMOST INVARIABLY EXPERIENCE THROMBOPHLEBITIS IF SULFOBROMOPHTHALEIN IS INJECTED INTO SAME ARM WITHIN FEW DAYS FOLLOWING INJECTION OF RADIOPAQUE SUBSTANCE.
VET WARNING: IRRITANT TO VEINS. USE DILUTE SOLN VIA SMALL GAUGE NEEDLES OR CANNULAS. ... ICTERIC STATES PREVENT INTERPRETATION OF TEST.
...USED WITH EXTREME CAUTION, IF @ ALL, IN PT WHO HAVE HAD PREVIOUS SULFOBROMOPHTHALEIN TESTS & IN PT WITH HISTORY OF ALLERGY OR ASTHMA... COMPLETE MEDICAL HISTORY...SHOULD BE OBTAINED BEFORE DYE IS ADMIN.
For more Drug Warnings (Complete) data for SODIUM SULFOBROMOPHTHALEIN (7 total), please visit the HSDB record page.

C20H8BR4NA2O10S2

838.00

833.609

71-67-0

297-83-6 (Parent)

6282

White to off-white solid powder

6.576

2

10

2

38

994

0

GHAFORRTMVIXHS-UHFFFAOYSA-L

InChI=1S/C20H10Br4O10S2.2Na/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);;/q;2*+1/p-2

disodium;2-hydroxy-5-[4,5,6,7-tetrabromo-1-(4-hydroxy-3-sulfonatophenyl)-3-oxo-2-benzofuran-1-yl]benzenesulfonate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: 500 mg/mL (596.66 mM)

Solubility in Formulation 1: ≥ 4.17 mg/mL (4.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 41.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 4.17 mg/mL (4.98 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 41.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 4.17 mg/mL (4.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 41.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)