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Also known as: 2321-07-5, Solvent yellow 94, Resorcinolphthalein, Yellow fluorescein, Fluoresceine, 3',6'-dihydroxy-3h-spiro[isobenzofuran-1,9'-xanthen]-3-one
Molecular Formula
C20H12O5
Molecular Weight
332.3  g/mol
InChI Key
GNBHRKFJIUUOQI-UHFFFAOYSA-N
FDA UNII
TPY09G7XIR

Fluorescein
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.
Fluorescein is a Diagnostic Dye. The mechanism of action of fluorescein is as a Dye.
1 2D Structure

Fluorescein

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
2.1.2 InChI
InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
2.1.3 InChI Key
GNBHRKFJIUUOQI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C(=C1)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
2.2 Other Identifiers
2.2.1 UNII
TPY09G7XIR
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 Dipotassium Salt

13. Fluorescein Disodium Salt

14. Fluorescein Monosodium Salt

15. Fluorescein Sodium, Minims

16. Fluorescein, Disodium

17. Fluorescein, Sodium

18. Fluoresceina, Colircusi

19. Fluoresceine, Minims

20. Fluorescite

21. Fluorets

22. Ful Glo

23. Ful-glo

24. Funduscein

25. Minims Fluorescein Sodium

26. Minims Fluoresceine

27. Minims Stains

28. Monosodium Salt, Fluorescein

29. Optifluor Diba

30. Sodium Fluorescein

31. Sodium, Fluorescein

32. Uranine

2.3.2 Depositor-Supplied Synonyms

1. 2321-07-5

2. Solvent Yellow 94

3. Resorcinolphthalein

4. Yellow Fluorescein

5. Fluoresceine

6. 3',6'-dihydroxy-3h-spiro[isobenzofuran-1,9'-xanthen]-3-one

7. 3,6-fluorandiol

8. D&c Yellow No. 7

9. Japan Yellow 201

10. D And C Yellow No. 7

11. C.i. Solvent Yellow 94

12. 3',6'-dihydroxyfluoran

13. Fluorescein Acid

14. Fluoreszein

15. Soap Yellow F

16. Hidacid Fluorescein

17. Resorcinol Phthalein

18. D & C Yellow No. 7

19. D+c Yellow No. 7

20. 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone

21. Fluorescein (free Acid)

22. 11712 Yellow

23. Chebi:31624

24. 9-(o-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one

25. Japan Yellow No. 201

26. Zlut Kysela 73

27. 3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one

28. Fluoran, 3',6'-dihydroxy-

29. Nsc 667256

30. 3',6'-fluorandiol

31. C.i. 45350:1

32. Mfcd00005050

33. Tpy09g7xir

34. Spiro[isobenzofuran-1(3h),9'-[9h]xanthen]-3-one, 3',6'-dihydroxy-

35. Chembl1057

36. Ci 45350:1

37. 3h-xanthen-3-one, 9-(o-carboxyphenyl)-6-hydroxy-

38. Nsc667256

39. Benzoic Acid, O-(6-hydroxy-3-oxo-3h-xanthen-9-yl)-

40. Nsc-667256

41. Nsc-759114

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

43. Ncgc00161643-03

44. 3',6'-dihydroxyspiro(isobenzofuran-1(3h),9'(9h)-xanthen)-3-one

45. 3',6'-dihydroxyspiro(isobenzofuran-1(3h),9'-(9h)xanthen)-3-one

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

47. 3,6-dihydroxyspiro(xanthene-9,3'-phthalide)

48. Dsstox_cid_18887

49. Dsstox_rid_79416

50. Dsstox_gsid_38887

51. 3',6'-dihydroxy-3h-spiro[2-benzofuran-1,9'-xanthen]-3-one

52. Fluorescein Red

53. Cas-2321-07-5

54. 3,6-dihydroxyspiro[xanthene-9,3'-phthalide]

55. Zlut Kysela 73 [czech]

56. Fluorecein

57. Diofluor

58. Ccris 7076

59. Hsdb 2128

60. Fluorescite (tn)

61. Diresorcinolphthalein

62. Einecs 219-031-8

63. Brn 0094324

64. Fluorescite (salt/mix)

65. 3',6' Dihydroxyfluoran

66. Fluorescein (jan/usp)

67. Fluorescein [ii]

68. Fluorescein [mi]

69. Unii-tpy09g7xir

70. Fluorescein [jan]

71. Fluorescein [hsdb]

72. Epitope Id:137337

73. Upcmld-dp087

74. Yellow 7 [inci]

75. Fluorescein [vandf]

76. Fluorescein [mart.]

77. Schembl16533

78. Fluorescein [usp-rs]

79. Fluorescein [who-dd]

80. Fluorescein [usp:ban:jan]

81. Ki201 [inci]

82. Dtxsid0038887

83. Upcmld-dp087:001

84. Acid Yellow 73 [inci]

85. Gnbhrkfjiuuoqi-uhfffaoysa-

86. Fluorescein (solvent Yellow 94)

87. C.i. 45350 (salt/mix)

88. Fluorescein [ep Monograph]

89. Hms2093f21

90. Hms3744c17

91. Moli001003

92. Pharmakon1600-01505396

93. Fluorescein [usp Monograph]

94. Amy22388

95. Hy-d0251

96. Zinc3860453

97. Tox21_113500

98. Tox21_303508

99. Bdbm50237588

100. C.i. Acid Yellow 73 (salt/mix)

101. Nsc759114

102. S5488

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

104. Akos015903296

105. Ccg-213417

106. Cs-7537

107. Db00693

108. C.i. 45350a

109. Fluorescein, For Fluorescence, Free Acid

110. Ncgc00161643-01

111. Ncgc00161643-02

112. Ncgc00257491-01

113. D & C Yellow No. 7 K7133

114. Sy012645

115. Sbi-0206827.p001

116. F0095

117. Fluorescein (free Acid), Dye Content 95 %

118. Ft-0668579

119. D01261

120. D70685

121. Ec 219-031-8

122. Ab00643381_02

123. 5-19-06-00456 (beilstein Handbook Reference)

124. Q410922

125. Sr-05000001696

126. Sr-05000001696-1

127. W-107417

128. Brd-k21913543-001-01-6

129. 3',6'-dihydroxyspiro[isobenzofuran-3,9'-xanthene]-1-one

130. E89fa0b4-4844-46a2-af9b-29eca50e5599

131. Fluorescein, European Pharmacopoeia (ep) Reference Standard

132. 3',6'-dihydroxy-3h-spiro[isobenzo[b]furan-1,9'-xanthen]-3-one

133. Fluorescein, United States Pharmacopeia (usp) Reference Standard

134. Fluorescein Low Range Dna Standard, Fluorescein-labeled Marker For Dna Electrophoresis

135. Spiro[isobenzofuran-1(3h),9'-[9h]xanthene]-ar-carboxylicacid, 3',6'-dihydroxy-3-oxo-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 332.3 g/mol
Molecular Formula C20H12O5
XLogP33.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Exact Mass332.06847348 g/mol
Monoisotopic Mass332.06847348 g/mol
Topological Polar Surface Area76 Ų
Heavy Atom Count25
Formal Charge0
Complexity522
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFluorescite
PubMed HealthFluorescein (Injection)
Drug ClassesDisclosing Agent
Drug LabelFLUORESCITE (fluorescein injection, USP) 10% contains fluorescein sodium (equivalent to fluorescein 10% w/v). It is a sterile solution for use intravenously as a diagnostic aid. Its chemical name is spiro[isobenzofuran-1(3H), 9'-[9H]xanthene]-3-one..
Active IngredientFluorescein sodium
Dosage FormInjectable
RouteIntravenous
Strengtheq 500mg base/5ml (eq 100mg base/ml)
Market StatusPrescription
CompanyAlcon Pharms

2 of 2  
Drug NameFluorescite
PubMed HealthFluorescein (Injection)
Drug ClassesDisclosing Agent
Drug LabelFLUORESCITE (fluorescein injection, USP) 10% contains fluorescein sodium (equivalent to fluorescein 10% w/v). It is a sterile solution for use intravenously as a diagnostic aid. Its chemical name is spiro[isobenzofuran-1(3H), 9'-[9H]xanthene]-3-one..
Active IngredientFluorescein sodium
Dosage FormInjectable
RouteIntravenous
Strengtheq 500mg base/5ml (eq 100mg base/ml)
Market StatusPrescription
CompanyAlcon Pharms

4.2 Therapeutic Uses

Contrast Medium

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


VET: Deep corneal ulcers, descemetocele, and iris prolapse are seen with some frequency in dogs, cats, and horses. ... Important diagnostic aids are the Schirmer tear test to measure aqueous tear production and topical fluorescein to examine the corneal ulcer. ...

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 1416


Fluorescein is now sometimes used for determination of circulation time, adequacy of blood supply, and viability of tissue.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1004


In determination of circulation time, ... by rapid iv ... appearance of fluorescence in lips, eyes, or intact skin or in wheals (histamine or scratch) ... is taken as end point.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1004


Measurement of arm-to-retina circulation time is employed for diagnosis of carotid artery occlusion.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 985


4.3 Drug Warning

Adverse effects following topical administration to the eye may include irritation and rash. Fluorescein may cause yellow discoloration of skin or eyes. urine may attain a bright yellow color. Adverse effects following intravenous administration include nausea, vomiting, headache, dizziness, fainting, and low blood pressure.

United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Fluorescein; Catalog Number: 1277004; (Revision Date: January 31, 2005)


4.4 Drug Indication

For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.


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 Active Moiety
FLUORESCEIN
5.2.2 FDA UNII
TPY09G7XIR
5.2.3 Pharmacological Classes
Dyes [MoA]; Diagnostic Dye [EPC]
5.3 ATC Code

S01JA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


S - Sensory organs

S01 - Ophthalmologicals

S01J - Diagnostic agents

S01JA - Colouring agents

S01JA01 - Fluorescein


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly distributed


Route of Elimination

Fluorescein and its metabolites are mainly eliminated via renal excretion.


Volume of Distribution

0.5 L/kg


Clearance

renal cl=1.75 mL/min/kg [After IV administration]

hepatic cl=1.50 mL/min/kg [After IV administration]


Fluorescence of skin persists for several hr, and dye appears in urine for as long as 30 hr.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1004


Within 7 to 14 seconds after IV administration into antecubital vein, fluorescein usually appears in the central 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 after 6 to 12 hours of dosing. Various estimates of volume of distribution indicate that fluorescein distributes well into interstitial space (0.5 L/ kg).

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


Fluorescein and its metabolites 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.

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


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

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


The permeability of the blood-retinal and blood-aqueous barriers to fluorescein and the rate of aqueous flow can be estimated by measurements of fluorescein in the vitreous, aqueous, and plasma after systemic administration. Fluorescein is commonly measured by fluorescence, but fluorescein glucuronide, a metabolite of fluorescein, also fluoresces. To assess the influence of fluorescein glucuronide on the quantitation of fluorescein by fluorescence, we studied the pharmacokinetics of fluorescein and fluorescein glucuronide for 38 hr in the plasma of five normal subjects given 14 mg/kg of sodium fluorescein intravenously. The plasma and the plasma ultrafiltrate were measured by fluorescence and by high performance liquid chromatography. In our fluorophotometer, fluorescein glucuronide was 0.124 times as fluorescent as fluorescein. Fluorescein was rapidly converted to fluorescein glucuronide, and within 10 min the concentration of unbound fluorescein glucuronide exceeded that of unbound fluorescein. The terminal half-lives of fluorescein and fluorescein glucuronide in the plasma ultrafiltrate were 23.5 and 264 min, respectively, so that fluorescein glucuronide contributed almost all of the plasma fluorescence after 4-5 hr. Because fluorescein glucuronide was less bound in the plasma than fluorescein, the ratio of the fluorescence of the plasma ultrafiltrate to that of the plasma increased with time. The greatest proportion of the total fluorescein available to penetrate into the ocular compartments occurred shortly after injection. ...

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


5.5 Metabolism/Metabolites

The permeability of the blood-retinal and blood-aqueous barriers to fluorescein and the rate of aqueous flow can be estimated by measurements of fluorescein in the vitreous, aqueous, and plasma after systemic administration. Fluorescein is commonly measured by fluorescence, but fluorescein glucuronide, a metabolite of fluorescein, also fluoresces. To assess the influence of fluorescein glucuronide on the quantitation of fluorescein by fluorescence, we studied the pharmacokinetics of fluorescein and fluorescein glucuronide for 38 hr in the plasma of five normal subjects given 14 mg/kg of sodium fluorescein intravenously. The plasma and the plasma ultrafiltrate were measured by fluorescence and by high performance liquid chromatography. In our fluorophotometer, fluorescein glucuronide was 0.124 times as fluorescent as fluorescein. Fluorescein was rapidly converted to fluorescein glucuronide, and within 10 min the concentration of unbound fluorescein glucuronide exceeded that of unbound fluorescein. The terminal half-lives of fluorescein and fluorescein glucuronide in the plasma ultrafiltrate were 23.5 and 264 min, respectively, so that fluorescein glucuronide contributed almost all of the plasma fluorescence after 4-5 hr. Because fluorescein glucuronide was less bound in the plasma than fluorescein, the ratio of the fluorescence of the plasma ultrafiltrate to that of the plasma increased with time. The greatest proportion of the total fluorescein available to penetrate into the ocular compartments occurred shortly after injection. ...

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


Fluorescein undergoes rapid metabolism 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, indicating relatively rapid conjugation.

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


Fluorescein is a known human metabolite of zinc15020070.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 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).


5.7 Mechanism of Action

Fluorescein sodium is used extensively as a diagnostic tool in the field of ophthalmology. Fluorescein is a fluorescent compound or fluorophore having a maximum absorbance of 494 m and an emission maximum of 521 nm. The yellowish-green fluorescence of the compound can be used to demarcate the vascular area under observation, distinguishing it from adjacent areas. It is applied topically in the form of a drop or it can be injected intravenously to produce a fluorescein angiogram. Topical fluorescein is a useful tool in the diagnosis of corneal abrasions, corneal ulcers, herpetic corneal infections, and dry eye. Fluorescein angiography is used to diagnose and categorize macular degeneration, diabetic retinopathy, inflammatory intraocular conditions, and intraocular tumors.


Fluorescein sodium responds to electromagnetic radiation and light between the wavelengths of 465-490 nm and fluoresces, i.e., emits light at wavelengths of 520-530 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. /Fluorescein sodium/

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


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23-Jan-2021
23-May-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.4%;0.2...DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.4%;0.25%

USFDA APPLICATION NUMBER - 208582

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DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.4%;0.3...DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.4%;0.3%

USFDA APPLICATION NUMBER - 211039

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