fluorescein

Small moleculeapproved

Approved

Nov 10, 1976

Fluorescein is a synthetic organic compound available as a dark orange/red powder slightly soluble in water and alcohol. It is widely used as a fluorescent tracer for many applications. Fluorescein was first synthesized by Adolf von Baeyer in 1871. It can be prepared from phthalic anhydride and resorcinol in the presence of zinc chloride via the Friedel-Crafts reaction. Fuorescein sodium is used intravenously in diagnostic fluorescein angiography or angioscopy of the retina and iris vasculature. 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. Topical, oral, and intravenous use of fluorescein can cause adverse reactions, including nausea, vomiting, hives, acute hypotension, anaphylaxis and related anaphylactoid reaction, causing cardiac arrest and sudden death due to anaphylactic shock. The most common adverse reaction is nausea, due to a difference in the pH from the body and the pH of the sodium fluorescein dye; a number of other factors however, are considered contributors as well. The nausea usually is transient and subsides quickly. Intravenous use has the most reported adverse reactions, including sudden death, but this may reflect greater use rather than greater risk. Both oral and topical uses have been reported to cause anaphylaxis, including one case of anaphylaxis with cardiac arrest (resuscitated) following topical use in an eye drop. Reported rates of adverse reactions vary from 1% to 6%. The higher rates may reflect study populations that include a higher percentage of persons with prior adverse reactions. The risk of an adverse reaction is 25 times higher if the person has had a prior adverse reaction. The risk can be reduced with prior (prophylactic) use of antihistamines and prompt emergency management of any ensuing anaphylaxis. A simple prick test may help to identify persons at greatest risk of adverse reaction — NCATS

Clinical trial activity

48 trials · 47 clinical orgs · 10 marketing orgs

Phase 1
15
Phase 2
16
Phase 3
3
Phase 4
6

Earliest trial started Aug 1, 2004 (NCT00856869)

Timeline

1970s

  1. Nov 10, 1976

    Novartis — Earliest FDA Approval

  2. Nov 10, 1976

    Novartis — NDA Secondary Org

  3. Nov 10, 1976

    Novartis — NDA Organization

2000s

  1. Jan 1, 2004

    Earliest Phase 1 Sponsor(trial)

  2. Mar 28, 2006

    Alcon — NDA Secondary Org

  3. Mar 28, 2006

    Nestle — NDA Secondary Org

  4. Jan 1, 2008

    Earliest Phase 2 Sponsor(trial)

  5. Jan 1, 2008

    Earliest Phase 3 Sponsor(trial)

  6. Aug 8, 2008

    Akorn, Inc. — NDA Secondary Org

  7. Aug 8, 2008

    LONG GROVE PHARMS — Marketing Organization

2010s

  1. Dec 14, 2017

    Altair Therapeutics — Marketing Organization

  2. Dec 14, 2017

    Altair Therapeutics — NDA Secondary Org

2020s

  1. Mar 9, 2020

    Bausch Health Companies — NDA Secondary Org

  2. Sep 25, 2023

    Nexus Pharmaceuticals — Marketing Organization

  3. Apr 30, 2026

    BPI — Marketing Organization

  4. Jun 1, 2026

    Zydus Discovery DMCC — Marketing Organization

Indications

Mechanism of action

  • Unspecified targetOTHER

    Disclosing agent

  • UnclearUnclear

    Unclear unclear

Combination products

Approval history

  • approvedNov 10, 1976

Chemistry & pharmacology

Loading structure…

SMILES

O=C(O)c1ccccc1-c1c2ccc(=O)cc-2oc2cc(O)ccc12
Mol. weight
332.31 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Availability
Prescription Only

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • 3',6'-dihydroxyfluoran
  • 3',6'-dihydroxyfluoran
  • 3,6-fluorandiol
  • 3,6-fluorandiol
  • 9-(o-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one
  • 9-(o-carboxyphenyl)-6-hydroxy-3h-xanthen-3-one
  • 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
  • 9-(o-carboxyphenyl)-6-hydroxy-3-isoxanthenone
  • ak-fluor
  • c.i. solvent yellow 94
  • c.i. solvent yellow 94
  • d and c yellow no. 7
  • d and c yellow no. 7
  • d&c yellow no. 7
  • d&c yellow no. 7
  • fluor-amps
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein
  • fluorescein acid
  • fluoresceine
  • fluoresceine
  • fluorescein lisicol
  • fluorescein sodium
  • fluorescein sodium
  • fluorescein sodium
  • fluorescein sodium
  • fluorescein sodium
  • fluorescein sodium
  • fluorescein, soluble
  • fluorescein, soluble
  • fluorescite
  • fluorescite
  • fluoreszein
  • fluoreszein
  • fluorets
  • fluorets
  • funduscein
  • funduscein
  • funduscein-25
  • funduscein-25
  • funduscein-25
  • japan yellow 201
  • japan yellow 201
  • nrl972
  • nrl972
  • resorcinolphthalein
  • resorcinolphthalein
  • resorcinolphthalein
  • retinofluor
  • sodium fluorescein
  • sodium fluorescein
  • solvent yellow 94
  • solvent yellow 94
  • uranin
  • vst-1001
  • yellow fluorescein
  • yellow fluorescein
  • yellow fluorescein

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06873815Phase 2Mar 7, 2025Memorial Sloan-Kettering Cancer Center
NCT06054178Phase 2Mar 31, 2024Stanford University
NCT05664555Phase 4Feb 1, 2023Seoul National University
NCT05556525N/ADec 15, 2022Mayo Clinic, National Cancer Institute (NCI)
NCT04597801Phase 2Oct 31, 2020Carl Zeiss Meditec, Inc., Technical University of Munich
NCT04687488N/AJul 23, 2020Katholieke Universiteit Leuven
NCT07230548Phase 3Jun 10, 2020Medical University of Vienna
NCT04351373Phase 2Jun 1, 2020Mayo Clinic
NCT04017975Phase 2Aug 31, 2019Harvard University, National Heart, Lung, and Blood Institute (NHLBI)
NCT04071080Phase 1Aug 22, 2019Medicor Research Inc., UpTru Inc.
NCT04008121Early Phase 1 (Phase 1)Jul 31, 2019MediBeacon
NCT03752203N/AJul 31, 2019University of Colorado, University of Colorado, Denver
NCT03189134Phase 1Apr 2, 2018Harvard University, National Heart, Lung, and Blood Institute (NHLBI)
NCT03297489Early Phase 1 (Phase 1)Nov 6, 2017State University of New York, Buffalo
NCT03291977Phase 3Oct 5, 2017University of Rennes
NCT03244982Phase 4Oct 1, 2017Kresge Eye Institute
NCT03220711Phase 1Jul 28, 2017University of Michigan
NCT02857374N/ANov 3, 2016National Cancer Institute (NCI), State University of New York, Buffalo
NCT02971800N/AAug 1, 2016Laval University
NCT02757417N/AJul 1, 2016Case Western Reserve University
Showing 20 of 48 trials
Page 1 / 3

Organizations

Research & Development (47)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
NorgineFor profit8832004
National Cancer Institute (NCI)Government4012009
State University of New York, BuffaloAcademic/Hospital3322013
University of UtahAcademic/Hospital3212008
Carl Zeiss Meditec, Inc.For profit2012016
Harvard UniversityAcademic/Hospital2222018
Mayo ClinicAcademic/Hospital2222020
MHAPT Zarita Johanna University HospitalAcademic/Hospital2012006
National Heart, Lung, and Blood Institute (NHLBI)Government2022018
Shandong UniversityAcademic/Hospital2222015
Stanford UniversityAcademic/Hospital2222009
St. Ivan Rilski's University HospitalAcademic/Hospital2022004
University of Colorado, DenverAcademic/Hospital2212015
Advent HealthAcademic/Hospital1112015
Baylor UniversityAcademic/Hospital1112009
Case Western Reserve UniversityAcademic/Hospital1112016
Columbia UniversityAcademic/Hospital1112015
Dartmouth UniversityAcademic/Hospital1112016
Duke UniversityAcademic/Hospital1012008
Hoosier Cancer Research NetworkAcademic/Hospital1112014
47 organizations
Page 1 / 3

Marketing (14)

OrganizationOrg typeRelationshipDate
Akorn, Inc.For profitNDA2Aug 8, 2008
AlconFor profitNDA2Mar 28, 2006
Altair TherapeuticsFor profitMKTGDec 14, 2017
Altair TherapeuticsFor profitNDA2Dec 14, 2017
BPIFor profitMKTGApr 30, 2026
Bausch Health CompaniesFor profitNDA2Mar 9, 2020
Bausch Health CompaniesFor profitNDA2Mar 9, 2020
LONG GROVE PHARMSFor profitMKTGAug 8, 2008
NestleFor profitNDA2Mar 28, 2006
Nexus PharmaceuticalsFor profitMKTGSep 25, 2023
Nexus PharmaceuticalsFor profitSYNSep 25, 2023
NovartisFor profitNDA2Nov 10, 1976
NovartisFor profitNDANov 10, 1976
Zydus Discovery DMCCFor profitMKTGJun 1, 2026