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 liver function is severely impaired, up to 10-25% of the drug may be excreted in the urine. Under normal circumstances, less than 2% of the dose is excreted in the urine, so extrahepatic clearance of sulfobromophthalein is negligible. Normal metabolism and excretion of sulfobromophthalein depend on hepatic blood flow, the ability of hepatocytes to take up and concentrate the dye, and bile excretion. Sulfobromophthalein is metabolized in the liver by binding with glutathione; both free and bound sulfobromophthalein are excreted in the bile. The dye does not pass through enterohepatic circulation and is primarily excreted in feces. After intravenous injection, the dye is usually completely eliminated within 24 hours. It is almost entirely bound to plasma proteins, primarily albumin and α1-lipoprotein. The dye is rapidly absorbed by hepatocytes and temporarily stored. A small amount of dye may be absorbed by skeletal muscle, but absorption by extrahepatic tissues is minimal. ...Does not cross the placenta. For more complete data on the absorption, distribution, and excretion of sulfobromophthalein (6 types), please visit the HSDB record page.

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Metabolism/Metabolites
S-aryltransferases are thought to be involved in the metabolism of sodium sulfobromophthalein…
It is excreted in rat bile as BSP-glutathione and other aminoacyl conjugates formed by the condensation of BSP with glutathione, possibly without the removal of any bromine atom.
Sodium sulfobromophthalein is metabolized to the following substances/in dogs: S-(3,3-bis(4-hydroxy-3-sulfophenyl)tribromophthalyl)glutathione; JAVITT NB et al., J CLIN INVEST, 39, 1570 (1960). Sodium sulfobromophthalein-β-D-glucuronide in the liver; HIRAYAMA C et al., SAISHIN IGAKU, 17, 2520 (1962).

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Biological Half-Life
In a study involving a small number of normal subjects, the average plasma half-life was approximately 4 minutes. The liver has a storage capacity... which is directly proportional to the concentration of dye in the plasma. For patients with normal liver function, 50-75 mg of sodium sulfobromophthalein can be stored per 100 ml of plasma per milligram of dye.

Interactions
Dehydrocholic acid, chlortetracycline, sulfonamides, neomycin, and monoamine oxidase inhibitors may also increase sulfobromophthalein retention; however, the possibility of actual liver injury should be considered in patients receiving chlortetracycline, sulfonamides, or neomycin. Concomitant use of indocyanine green… may lead to impaired hepatic excretion… Cholecystography agents… have been reported to competitively interfere with the clearance and excretion of sulfobromophthalein… ethoxyziridazine, phenapyridine, phenolphthalein, and phenolsulfonphthalein (PSP) may reduce the apparent excretion of sulfobromophthalein by interfering with colorimetric assays… Pretreatment of rats with phenobarbital and other microsomal enzyme inducers increased both bile excretion and plasma clearance of sulfobromophthalein, and the increase in excretion was closely related to the increase in bile flow rate. For more complete data on interactions of sulfobromophthalein (7 in 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.

Sodium bromosulfonphthalein is an organosodium salt, the disodium salt of bromosulfonphthalein. It is used as a dye. It contains a bromosulfonphthalein (2-) group. Its function is related to 2-benzofuran-1(3H)-one. A phenolphthalein compound used as an adjunct to liver function tests. Mechanism of Action: The bromosulfonphthalein liver function test is based on the fact that in patients with abnormal liver function, the clearance and estimated storage capacity of the dye are decreased, while the plasma half-life and estimated excretion time are prolonged. Therapeutic Uses: Indicator and reagent; phthalocyanine dye. 45 minutes after injection… 4-5 ml of blood is drawn from the contralateral arm to avoid sample contamination. …Some clinicians collect a single sample at 30 minutes, others at 60 minutes. The amount of residual dye in serum is determined by colorimetry. Uses… In liver function tests, the basis is not pharmacological action, but rather its distribution, metabolism, and excretion in the body.
...It helps detect liver damage in patients exposed to hepatotoxins and to identify metastatic cancer. It has also been used to differentiate upper gastrointestinal bleeding caused by peptic ulcers from upper gastrointestinal bleeding caused by esophageal varices, and to diagnose Durbin-Johnson syndrome or Rotor syndrome. Used to assess hepatic blood flow...
For more complete data on the therapeutic uses of sodium sulfobromophthalein (8 types), please visit the HSDB record page.

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Drug Warnings
Hyperbilirubinemia may interfere with the measurement of sodium sulfobromophthalein...Heparin...increases the color intensity in serum...and causes changes in absorption...Sodium sulfobromophthalein may cause elevations in other laboratory test results...serum calcium, serum creatine and creatinine, urobilinogen, hemoglobin...
Parenteral cholecystography contrast agents are saturated solutions. Thrombophlebitis will almost certainly occur if sodium sulfobromophthalein is injected into the same arm within days after the injection of a radioactive contrast agent.
Veterinary Warning: Irritates veins. Use a diluted solution and inject through a fine needle or cannula. Jaundice can interfere with the interpretation of test results.
Use with extreme caution, or avoid use altogether, in patients who have previously undergone testing for sulfobromophthalein sodium or who have a history of allergies or asthma. …A complete medical history should be obtained before injecting the dye.
For more complete data on drug warnings for sulfobromophthalein sodium (7 in total), please visit the HSDB records 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.)