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Fluorescein Sodium

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Macsen Fluorescein Sodium

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Also known as: Fluorescein disodium salt, Soluble fluorescein, Uranin, Sodium fluorescein, Fluorescein, disodium salt, C.i. acid yellow 73

Molecular Formula

C₂₀H₁₀Na₂O₅

Molecular Weight

376.3 g/mol

InChI Key

NJDNXYGOVLYJHP-UHFFFAOYSA-L

FDA UNII

93X55PE38X

A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.

1 2D Structure

Fluorescein Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate

2.1.2 InChI

InChI=1S/C20H12O5.2Na/c21-11-5-7-15-17(9-11)25-18-10-12(22)6-8-16(18)19(15)13-3-1-2-4-14(13)20(23)24;;/h1-10,21H,(H,23,24);;/q;2*+1/p-2

2.1.3 InChI Key

NJDNXYGOVLYJHP-UHFFFAOYSA-L

2.1.4 Canonical SMILES

C1=CC=C(C(=C1)C2=C3C=CC(=O)C=C3OC4=C2C=CC(=C4)[O-])C(=O)[O-].[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

93X55PE38X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. C.i. 45350

2. Colircusi Fluoresceina

3. D And C Yellow No. 7

4. D And C Yellow No. 8

5. Diofluor

6. Dipotassium Salt, Fluorescein

7. Disodium Fluorescein

8. Disodium Salt, Fluorescein

9. Fluor I Strip A.t.

10. Fluor-i-strip A.t.

11. Fluorescine Sodique Faure

12. Fluorescein

13. Fluorescein Dipotassium Salt

14. Fluorescein Disodium Salt

15. Fluorescein Monosodium Salt

16. Fluorescein Sodium, Minims

17. Fluorescein, Disodium

18. Fluorescein, Sodium

19. Fluoresceina, Colircusi

20. Fluoresceine, Minims

21. Fluorescite

22. Fluorets

23. Ful Glo

24. Ful-glo

25. Funduscein

26. Minims Fluorescein Sodium

27. Minims Fluoresceine

28. Minims Stains

29. Monosodium Salt, Fluorescein

30. Optifluor Diba

31. Sodium Fluorescein

32. Sodium, Fluorescein

33. Uranine

2.3.2 Depositor-Supplied Synonyms

1. Fluorescein Disodium Salt

2. Soluble Fluorescein

3. Uranin

4. Sodium Fluorescein

5. Fluorescein, Disodium Salt

6. C.i. Acid Yellow 73

7. Resorcinol Phthalein Sodium

8. Uranine Wss

9. C.i. 45350

10. Fluorescein, Soluble

11. Ki202

12. 93x55pe38x

13. Disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate

14. Ki202(1)

15. Ki202(2)

16. Disodium 2-(6-oxido-3-oxo-3h-xanthen-9-yl)benzoate

17. Ci 45350

18. Aizen Uranine

19. Calcocid Uranine B4315

20. Spiro(isobenzofuran-1(3h),9'-(9h)xanthen)-3-one, 3',6'-dihydroxy-, Sodium Salt (1:2)

21. Spiro(isobenzofuran-1(3h),9'-(9h)xanthene)-3-one, 3'6'-dihydroxy, Disodium Salt

22. Funduscein

23. Flurenate

24. Furanium

25. Obiturine

26. Hidacid Uranine

27. Uranine Yellow

28. Fluorescein Lt

29. Fluoresein Sodium

30. Uranine A

31. Uranine O

32. Ak-fluor

33. Uranin A

34. Uranin S

35. Uranine A Extra

36. Uranine Ss

37. Fluor-i-strip

38. Yellow 8

39. Soluble Fluoresceine

40. Floures (tn)

41. Sodium Fluoresceinate

42. Certiqual Fluoresceine

43. Fluoresceinum Natricum

44. Fluorescein Free Acid

45. Basacid Yellow 226

46. Fluor-i-strip A.t.

47. Fluorescein Sodium B.p

48. D&c Yellow No. 8

49. Fluorescein, Sodium Salt

50. 11824 Yellow

51. 12417 Yellow

52. Soluble Fluoresceine Bps

53. Japan Yellow 202(1)

54. D & C Yellow No. 8

55. Acid Yellow 73 Sodium Salt

56. Schembl264060

57. Unii-93x55pe38x

58. Ci 45350 (na Salt)

59. Ccris 6239

60. Chembl1628233

61. Fluorescein Sodium [jan]

62. Fluorescein Sodium (jp17/usp)

63. Hsdb 8007

64. Fluorescein Sodium [vandf]

65. Ki202(1) [inci]

66. Ki202(2) [inci]

67. Moli001004

68. Nci-c54706

69. Fluorescein Sodium [mart.]

70. Fluorescein Sodium [usp:ban:jan]

71. Fluorescein Sodium [who-dd]

72. Fluorescein Sodium [who-ip]

73. Nsc 5070

74. Einecs 208-253-0

75. Akos024364966

76. Fluorescein Disodium Salt [mi]

77. Fluorescein Sodium [ep Impurity]

78. Fluorescein Sodium [orange Book]

79. Fluorescein Sodium [ep Monograph]

80. As-17142

81. Fluorescein Sodium [usp Monograph]

82. F0096

83. Fluoresceinum Natricum [who-ip Latin]

84. Ft-0626450

85. D02024

86. Disodium 6-hydroxy-3-oxo-9-xanthene-o-benzoate

87. Sodium Salt Of Hydroxy-o-carboxy-phenyl-fluorone

88. Fluorescein Sodium Component Of Altafluor Benox

89. Q27271622

90. Z1262246141

91. 9-o-carboxyphenyl-6-hydroxy-3-isoxanthone, Disodium Salt

92. Benzoic Acid, 2-(6-hydroxy-3-oxo-3h-xanthen-9-yl)-, Disodium Salt

93. 3',6'-dihydroxyspiro(isobenzofuran-1(3h),9'-(9h)xanthen)-3-one, Disodium Salt

94. Spiro(isobenzofuran-1(3h),9'-(9h)xanthen)-3-one, 3',6'-dihydroxy-, Disodium Salt

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₀Na₂O₅
Molecular Weight	376.3 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	376.03236198 g/mol
Monoisotopic Mass	376.03236198 g/mol
Topological Polar Surface Area	89.5 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	644
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

Contrast Media; Fluorescent Dyes

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

/Fluorescein sodium/ 10% (100 mg/mL) and 25% (250 mg/mL) is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for AK-FLUOR (fluorescein sodium) injection (August 2011). Available from, as of October 21, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a1823be3-a739-48bc-a3ea-ceb7cc5105ce

Fluorescein injection, (USP) 10% is indicated in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature.

US Natl Inst Health; DailyMed. Current Medication Information for Fluorescite (fluorescein sodium) injection, solution (2009). Available from, as of October 19, 2009: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=Fluorescein+sodium

Uranine is used topically in the fitting of hard contact lenses and in other ocular diagnostic and therapeutic areas, particularly in corneal challenges.

The National Academies; Institute of Medicine: Health Effects of Project Shad Chemical Agent: Uranine Dye (Sodium Fluorescein) 518-47-8 p. 5 (2004). Available from, as of October 24, 2011: https://www.iom.edu/Reports.aspx

For more Therapeutic Uses (Complete) data for D&C Yellow No. 8 (9 total), please visit the HSDB record page.

4.2 Drug Warning

/Fluorescein sodium/ is contraindicated in patients with known hypersensitivity to fluorescein sodium or any other ingredients in this product. Rare cases of death due to anaphylaxis have been reported.

Caution should be exercised in patients with a history of allergy or bronchial asthma. An emergency tray should always be available.

If a potential allergy is suspected, an intradermal skin test may be performed prior to intravenous administration, i.e., 0.05 mL injected intradermally to be evaluated 30 to 60 minutes following injection. Given the sensitivity and specificity of skin testing, a negative skin test is not proof that a patient is not allergic to fluorescein.

Extravasation during injection can result in severe local tissue damage due to high pH of fluorescein solution. The following complications resulting from extravasation of fluorescein have been noted to occur: Sloughing of the skin, superficial phlebitis, subcutaneous granuloma, and toxic neuritis along the median nerve in the antecubital area. Complications resulting from extravasation can cause severe pain in the arm for up to several hours. When extravasation occurs, the injection should be discontinued and conservative measures to treat damaged tissue and to relieve pain should be implemented.

For more Drug Warnings (Complete) data for D&C Yellow No. 8 (13 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Contrast Media

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

Fluorescent Dyes

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Dyes [MoA]; Diagnostic Dye [EPC]

5.3 Absorption, Distribution and Excretion

Uranine is rapidly absorbed in the lungs and in the respiratory tract, and is affected by the presence of surfactants. It is not metabolized in the lung. Inhaled uranine is excreted in the urine.

The National Academies; Institute of Medicine: Health Effects of Project Shad Chemical Agent: Uranine Dye (Sodium Fluorescein) 518-47-8 p. 9 (2004). Available from, as of October 24, 2011: https://www.iom.edu/Reports.aspx

Within 7 to 14 seconds after IV administration into the antecubital vein, fluorescein usually appears in the central retinal artery of the eye. Within a few minutes of IV administration of fluorescein sodium, a yellowish discoloration of the skin occurs, which begins to fade 6 to 12 hours after dosing. Various estimates of volume of distribution indicate that fluorescein distributes into interstitial space (0.5 L/kg).

Fluorescein sodium has been demonstrated to be excreted in human milk.

Fluorescein and its metabolite are mainly eliminated via renal excretion. After IV administration, the urine remains slightly fluorescent for 24 to 36 hours. A renal clearance of 1.75 mL/min/kg and a hepatic clearance (due to conjugation) of 1.50 mL/min/kg have been estimated. The systemic clearance of fluorescein was essentially complete by 48 to 72 hours after administration of 500 mg fluorescein.

For more Absorption, Distribution and Excretion (Complete) data for D&C Yellow No. 8 (7 total), please visit the HSDB record page.

5.4 Metabolism/Metabolites

Fluorescein is metabolized to fluorescein monoglucuronide. After IV administration of fluorescein sodium (14 mg/kg) to 7 healthy subjects, approximately 80% of fluorescein in plasma was converted to glucuronide conjugate after a period of 1 hour post dose.

5.5 Biological Half-Life

... The pharmacokinetics of fluorescein and fluorescein glucuronide /were studied/ for 38 hr in the plasma of five normal subjects given 14 mg/kg of sodium fluorescein intravenously. ... The terminal half-lives of fluorescein and fluorescein glucuronide in the plasma ultrafiltrate were 23.5 and 264 min, respectively, ... .

PMID:3721789 Blair NP et al; Invest Ophthalmol Vis Sci 27 (7): 1107-14 (1986).

5.6 Mechanism of Action

Fluorescein sodium responds to electromagnetic radiation and light between the wavelengths of 465 to 490 nm and fluoresces, i.e., emits light at wavelengths of 520 to 530 nm. Thus, the hydrocarbon is excited by blue light and emits light that appears yellowish green. Following intravenous injection of fluorescein sodium in an aqueous solution, the unbound fraction of the fluorescein can be excited with a blue light flash from a fundus camera as it circulates through the ocular vasculature, and the yellowish green fluorescence of the dye is captured by the camera. In the fundus, the fluorescence of the dye demarcates the retinal and/or choroidal vasculature under observation, distinguishing it from adjacent areas/structures.

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