Please Wait

Applying Filters...

Technical details about DSSTox_CID_3621, learn more about the structure, uses, toxicity, action, side effects and more

DSSTox_CID_3621

Synopsis, Chemistry

DOSSIERs // Finished Dosage Forms

1 Dossiers, 1 Europe

GLOBAL SALES INFORMATION

1 Finished Drug Prices

1 Finished Drug Prices

DSSTox_CID_3621
Chemistry
Full Screen View

1. Also known as: Bromosulfalein, 71-67-0, Bromsulphalein, Bromthalein, Bromosulphthalein, Hepatestabrome

Molecular Formula

C₂₀H₈Br₄Na₂O₁₀S₂

Molecular Weight

838.0 g/mol

InChI Key

GHAFORRTMVIXHS-UHFFFAOYSA-L

A phenolphthalein that is used as a diagnostic aid in hepatic function determination.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

GHAFORRTMVIXHS-UHFFFAOYSA-L

2.1.4 Canonical SMILES

C1=CC(=C(C=C1C2(C3=C(C(=C(C(=C3Br)Br)Br)Br)C(=O)O2)C4=CC(=C(C=C4)O)S(=O)(=O)[O-])S(=O)(=O)[O-])O.[Na+].[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bromosulphthalein

2. Bromsulphalein

3. Bromthalein

4. Disodium, Sulfobromophthalein

5. Sodium, Sulfobromophthalein

6. Sulfobromophthalein

7. Sulfobromophthalein Disodium

8. Sulfobromophthalein Sodium

9. Tetrabromsulphthalein

2.2.2 Depositor-Supplied Synonyms

1. Bromosulfalein

2. 71-67-0

3. Bromsulphalein

4. Bromthalein

5. Bromosulphthalein

6. Hepatestabrome

7. Hepatosulfalein

8. Hepartest

9. Bromsulphthalein

10. Bsp Sodium

11. Bromsulfalein

12. Sodium Bromosulfalein

13. Sodium Bromsulphalein

14. Sodium Bromsulphthalein

15. Sodium Bromosulfophthalein

16. Sodium Sulphobromophthalein

17. Sulphobromophthalein Sodium

18. Disodium Bromosulfophthalein

19. Tetrabromophenolsulfophthalein

20. Sodium Phenol Tetrabromophthalein

21. Sodium Sulfobromophthalein

22. Sulfobromophthalein Disodium Salt

23. Disodium Phenoltetrabromophthalein Sulfonate

24. Chebi:63827

25. 4,5,6,7-tetrabromo-3',3''-disulfophenolphthalein Disodium Salt

26. Dsstox_cid_3621

27. Dsstox_rid_77114

28. Dsstox_gsid_23621

29. Bromsulfthalein

30. Hepartestabrome

31. Bromotaleina

32. Brom-tetragnost

33. Bromsulfophthalein

34. Bsf Simes

35. Cas-71-67-0

36. Benzenesulfonic Acid, 3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)bis(6-hydroxy-, Disodium Salt

37. Benzenesulfonic Acid, 3,3'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)bis[6-hydroxy-, Disodium Salt

38. Bsf

39. Disodium 3,3'-(4,5,6,7-tetrabromo-3-oxo-1,3-dihydro-2-benzofuran-1,1-diyl)bis(6-hydroxybenzenesulfonate)

40. Cbsp

41. Bromsulphalein R Sodium

42. Ncgc00159391-02

43. Ncgc00159391-03

44. Unii-62e5ju30ov

45. Hsdb 2183

46. Disodium 2-hydroxy-5-[4,5,6,7-tetrabromo-1-(4-hydroxy-3-sulfonatophenyl)-3-oxo-1,3-dihydro-2-benzofuran-1-yl]benzene-1-sulfonate

47. Einecs 200-761-0

48. Sulfobromophthalein Sodium [usp:jan]

49. Bromsulphthalein Sodium

50. Bromosulfophthalein Sodium

51. [3h]bsp

52. Disodium 6,6'-dihydroxy-3,3'-(4,5,6,7-tetrabromo-1,3-dihydro-3-oxoisobenzofuran-1-ylidene)dibenzenesulphonate

53. Schembl487073

54. [3h]-bsp

55. Chembl453904

56. Gtpl4505

57. Gtpl4506

58. Bromosulfophthalein Disodium Salt

59. Dtxsid9023621

60. Sulfobromophthalein Sodium (jp17)

61. Sulfobromophthaleinsodiumtetrahydrate

62. Tox21_111628

63. Akos024373601

64. Tox21_111628_1

65. 5,5'-(4,5,6,7-tetrabromo-3-oxo-1(3h)-isobenzofuranylidene)bis(2-hydroxybenzenesulfonic Acid) Disodium Salt

66. Ft-0643010

67. D02210

68. Q926998

69. 4,5,6,7-tetrabromo-3',3'-disulfophenolphthalein Disodium Salt

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₈Br₄Na₂O₁₀S₂
Molecular Weight	838.0 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	2
Exact Mass	837.60468 g/mol
Monoisotopic Mass	833.60878 g/mol
Topological Polar Surface Area	198 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	994
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Therapeutic Uses

Indicators and Reagents; Phthalein Dyes

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

USE...IN HEPATIC FUNCTION DETERMINATION IS NOT BASED ON ITS PHARMACOLOGIC EFFECTS BUT ON ITS DISTRIBUTION, METABOLISM, & EXCRETION FROM BODY.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

...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...

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

For more Therapeutic Uses (Complete) data for SODIUM SULFOBROMOPHTHALEIN (8 total), please visit the HSDB record page.

4.2 Drug Warning

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...

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

VET WARNING: IRRITANT TO VEINS. USE DILUTE SOLN VIA SMALL GAUGE NEEDLES OR CANNULAS. ... ICTERIC STATES PREVENT INTERPRETATION OF TEST.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 578

...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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

For more Drug Warnings (Complete) data for SODIUM SULFOBROMOPHTHALEIN (7 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)

Coloring Agents

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

5.2 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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

NORMAL METABOLISM & EXCRETION OF SULFOBROMOPHTHALEIN DEPEND ON HEPATIC BLOOD FLOW, ABILITY OF LIVER CELLS TO TAKE UP & CONCN THE DYE, & INTAKE BILIARY EXCRETION.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

...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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

For more Absorption, Distribution and Excretion (Complete) data for SODIUM SULFOBROMOPHTHALEIN (6 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

S-ARYLTRANSFERASE IS THOUGHT TO BE INVOLVED IN METABOLISM OF SULFOBROMOPHTHALEIN...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 368

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.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 25

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).

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. S-15

5.4 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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

5.5 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.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 36:44

POST ENQUIRY